Sports contracts are a tricky thing. Do you pay a player for his past greatness? Or do you try to project how they will perform as the clock turns past their 30th birthday? And if you’re in a league with a salary cap, things get even harder as you try to plan out an entire roster without going over budget. No matter how careful teams are, there have been some egregious mistakes over the years.

While MLB probably holds the crown for “Most Terrible Contracts” due to every deal being fully guaranteed in a league with no salary cap, plenty of other major sports have eye-popping contracts that should have been shredded on sight instead of signed, sealed, and delivered to the commissioner’s office. This article will give you, in no particular order, a breakdown of some of the worst, most regrettable contracts in North American sports history.

40. Matt Cain – San Francisco Giants

For a five-year period late between 2007 and 2012, there weren’t many pitchers as durable or as busy as the Giants’ Matt Cain. Starting in 2007, the big righty started 32 games and pitched 200 innings. For the next five campaigns, Cain started anywhere from 33 to 34 games and recorded well over 200 innings each year. In that time his record was 70-65 and his ERA clocking in from a low of 2.79 in 2012 to a high of 3.76 in 2008.

For all his hard work, the Giants rewarded him with a six-year, $112.5 million extension in early in 2012. He rewarded the team with a perfect game (the 22nd in major league history) during that 2012 season, his best in the majors, but it’s been all downhill since. After going 8-10 with a 4.00 ERA in 30 starts in 2013, the three-time All-Star has been hampered by injuries and inconsistency. His 2017 year was a “comeback” of sorts, as he started over 20 games for the first time since 2013 (23), but his numbers were among the most dismal. He went 3-11, with a 5.43 ERA and career worst 1.657 WHIP and then promptly retired.

(AP Photo/Ross D. Franklin)

39. Marc Staal – New York Rangers

Back in 2017-18, the Rangers were in a good cap situation with few fat contracts impeding growth and Rick Nash’s $7.8 million coming off the books (second highest salary on the team). Yet, there is one deal they may want a do-over on and that one belongs to veteran defenceman Marc Staal. A dependable two-way defenceman who isn’t a big scorer, the 31-year-old signed a lucrative six-year, $34.2 million contract with the Blueshirts in 2015-16.

Now a third-pair defenceman, he soaks up $5.7 million of New York cap space and has seen his average ice time decrease a lot since his prime years. It’s a pretty hefty chunk of change to give a guy who doesn’t play on the powerplay and whose numbers have slowly ebbed down — he scored just 8 points in 2017-18, and only 13 points in 2018-19, while also posting a -9 +/- on the season.

(AP Photo/Julie Jacobson)

38. Russell Martin – Toronto Blue Jays

In the last year of his previous contract, Russell Martin had one of the best years of career. While playing for the Pirates in 2014, Martin slashed .290/.402/.430 with 11 home runs, 67 RBI, and 59 walks, playing backcatcher in 111 games. That performance was enough to attract a bunch of suitors when he hit free agency that winter, and the Toronto Blue Jays came calling for the Canadian native.

The Jays inked Martin to a five-year, $82 million contract — that’s a lot of money for a catcher! After he moved north, his batting average plummeted below .250. His power numbers went up slightly, but so did his strikeouts, as the Jays turned into a homer-or-strikeout type of team. In 2017 he only played in 91 games, limited by injuries. In 2018, he played another 90 but saw his average sink to a dismal .194, cranking out just 10 homers on the year. The Jays traded him to the Dodgers ahead of the 2019 season, but had to eat a lot of his remaining salary to make it happen. Meanwhile the Dodgers are barely using him, with the highlights so far being his two emergency relief pitching appearances. Yep, you read that right.

THE CANADIAN PRESS/Nathan Denette

37. Vernon Wells – Toronto Blue Jays

It’s a given that good-to-great players get paid for what they did before, not what they do after signing a big contract. In the Toronto Blue Jays case, management probably wished they’d had a crystal ball when they handed All-Star outfielder Vernon Wells a seven-year, $126 million contract after his monster 2006 season. It was tied for the 60th biggest contract in sports, all-time.

By 2007, his batting average dipped nearly 60 points from 2006 (.303 to .245) and his homers were halved (32 to 16). In an injury shortened 2008 season, he did make a marginal comeback, hitting .300 in 108 games, but for five more seasons, two with Toronto, two with the Angels and one with the Yankees, Wells was strictly ho-hum at the plate. It’s a good thing Wells was an exemplary human being, what with the induction into the Baseball Humanitarians Hall of Fame in 2010.

THE CANADIAN PRESS/Darren Calabrese

36. Andrea Pirlo – New York City FC

Don’t fire up those hate emails just yet, Italian soccer fans. Andrea Pirlo is a certified football legend, having a storied career for the likes of AC Milan, Juventus, and the Italian National Team. He has multiple Serie A titles, a pair of Copa Italia trophies, and two Champions League winners medals. Oh, and a World Cup championship with Italy in 2006. The grand old maestro of Italian football made the jump to MLS in 2015, signing a DP contract to join the New York Yankees/Manchester City-owned expansion team in the middle of their debut season.

Pirlo was already 36 by the time he joined NYCFC, and his age showed. There were still flashes of his old technical brilliance, but here are some hard facts: the MLS is a league that thrives on speed and athleticism, and doesn’t always reward beautiful football. Pirlo scored just a single goal in 62 appearances for the MLS version of the Sky Blues, and was often criticized for his lack of hustle and sub-par defensive efforts. You could usually spot him lingering around the center circle, hoping someone would pass him the ball so he could ping off a 40-yard pass that required very little actual running on his part. To his credit, he did manage 18 assists in his two and half seasons in the Big Apple.

By 2017, Pirlo’s body was giving him all he signs. He announced he would retire at the end of the season, and was limited to just 15 appearances in his final professional campaign. Pirlo is still one of the all-time greats, but his time in MLS appeared to be not much more than a ploy to sell shirts and season tickets to the Italian community in New York.

(AP Photo/Jason DeCrow)

35. Pablo Sandoval – Boston Red Sox

This season, the San Francisco Giants will finally pay Pablo Sandoval what he’s worth. At $555,000, it’s a far cry from the $18 million average he was making in Boston for a couple of years after signing a whopping five-year, $90 million deal in late 2014. Kung Fu Panda, who was a two-time All-Star with the Giants and played seven good to great seasons with them, took the money and ran to Beantown.

Well, let’s say the portly third baseman waddled there and struggled to maintain a healthy weight for all of 161 games in parts of three seasons. He had just six at bats in 2016 and was shut down for shoulder surgery and then struggled badly in 2017, hitting just .212 in 32 games with four homers before being bought out and waived by Boston. The Giants picked him back up in 2017 for the league minimum and he’s sort of bounced back to being an average MLB player again. Yep, that’s (sort of) worth $535,000, but not the eight-figure paydays that the Red Sox are still on the hook for while he plays in California.

(AP Photo/Marcio Jose Sanchez)

34. Jose Reyes – New York Mets

After six mostly uninspiring and controversy fueled seasons (he was suspended 51 games in 2016 for alleged domestic violence), shortstop Jose Reyes six-year, $106 million contract he signed with Miami way back in 2012 has finally run its course. In those six years, Reyes was traded to Toronto after a lone great season with the Marlins in 2012 and the Blue Jays were so unimpressed with his lack of defense they flipped him to Colorado at the 2015 deadline for Troy Tulowitzki.

He was neither very good, nor very bad, in 47 games with the Rockies after that, however, in the aftermath of the suspension he was bought out of that contract and designated for assignment, where he was picked up for a second go around with the New York Mets. They paid him the league minimum for parts of two seasons, where he hit .246 in 2017 and just .189 in 2018. He became a free agent, but another job in the Bigs has not appeared so far.

(AP Photo/Charles Rex Arbogast)

33. Jayson Werth – Washington Nationals

Jayson Werth’s contract is a perfect example of paying for what a man has done previously. After an All-Star campaign with Philadelphia in 2009, followed by seven homers in Philly’s run to a World Series triumph and then another great year in 2010, the hirsute slugger signed a seven-year, $126 million deal to play in Washington, D.C.

He rewarded his new club with a horrendous 2011 campaign, highlighted by a June where he boasted a .154 batting average, a .291 on-base percentage, and a .286 slugging percentage. In 2012, Werth broke his left wrist on a diving catch, against his ex-team no less, missing exactly half the schedule. In 2013, Werth finished 13th in NL MVP voting after batting .318 with 25 homers and 82 RBI and had a decent 2014, hitting .292 with 16 HR and 82 RBI. It’s been a severely sliding scale since, as he hit .221 an injury filled 2015 and “improved” to .244 in 2016. Werth managed just 70 games in 2017 for his $21 million, hitting .226 with 10 homers. He attempted to continue his career by signing a minor league deal with the Mariners in early 2018, but announced his retirement just three months later.

(AP Photo/David Banks)

32. Shea Weber – Nashville Predators

The Montreal Canadiens will surely end up eating a large portion of Shea Weber’s monster contract in the near future. It seemed like a good idea at the time in the summer of 2016, swinging a huge deal with Nashville to bring in the tough offensive defenceman and leader, sending P.K. Subban the other way. Already 30 when the Habs obtained him, the well-compensated rearguard showed cracks of his age early, and has spent much of his Montreal career on the injured list (while PK thrived in Smashville).

Weber signed a massive front loaded 14-year, $110 million contract with Nashville in 2012 ($68 million as signing bonus). It doesn’t expire until the 2025-26 season when he’ll be 39. Montreal will pay him a sliding scale of $6 million per year from 2018 to 2022, then $3 million for one and $1 million for three more. That is, unless they can find a way to deal him and his fat pact elsewhere. He only played 26 games in 2017-18, and 58 in 2018-19. And he’s not getting any younger.

THE CANADIAN PRESS/Paul Chiasson

31.   Johan Santana – New York Mets

Pre-Clayton Kershaw, Johan Santana was one of the most feared southpaws in baseball. The Venezualan wonder won two Cy Young awards with the Minnesota Twins in 2004 and 2006 and was in the running five years straight. Thus, it seemed like a good idea for the Mets, who acquired him in a trade with the Twins in February 2008, to lock up the then-28-year-old long term, to the tune of seven years and $137.5 million.

He had a Cy Young worthy 2008 with New York, going 16-7, but by 2013 and two full campaigns on the DL (2011 and ’13) the Mets were forced to buy out Santana’s contract, shelling out $5.5 million to pay off the lefthander’s $25 million option for 2014. While he did toss a no-hitter in 2012, his dismal numbers and career-ending injuries make his contract one of the worst ever signed. After an ill-fated minor league tryout with Toronto in 2015 (he never made it back to the majors), his baseball career was over.

(AP Photo/Frank Franklin II)

(AP Photo/Frank Franklin II)

30.   Melvin Upton Jr. – Atlanta Braves

When managers are discussing “bad contracts” or players to “dump”, the man formerly known as B.J. Upton immediately springs to mind, especially for the Atlanta Braves. Early in his career with Tampa Bay, the Norfolk, Virginia native was a dual threat offensively, hitting for power (113 HR between 2007-12) and stealing bases (217 in six seasons). After a stellar 2012 season, Upton signed the largest free agent contract in Braves history (at the time), a five-year, $72.5 million deal.

What he gave the Braves for that pact was just a whole lot of grief, with his reputation as being a slacker following him (he was disciplined twice in Tampa for lack of hustle). Those incidences should have been a harbinger of things to come, as Upton didn’t put in the work to improve a terrible .184 batting average in 2013, along with the worst strikeout rate (151 in just 446 plate appearances) in the the National League. The Braves tired of his act and dealt him to San Diego, where he improved somewhat, later getting short look-see from Toronto. He’s been out of baseball since 2016.

(AP Photo/Lenny Ignelzi)

(AP Photo/Lenny Ignelzi)

29. Dion Phaneuf – Toronto Maple Leafs

The Ottawa Senators are fairly horrible in recent years and part of the reason for that is the play of a diminishing asset like 32-year-old defenceman Dion Phaneuf. Once a three or four D-man in Toronto, he was signed to top tier money in the middle of the 2013-14 season. It was a pretty hefty deal (seven years, $49 million; ninth highest among rearguards) for a guy who was years removed from being a Norris Trophy candidate in Calgary and whose leadership (remember salute-gate?) was questionable.

Phaneuf’s stats declined after signing the pact, to the point he went from a +3 in 2013-14, to a -11 in 10 fewer games in 2014-15. However, Leafs management pulled off the purge of the decade by shipping Phaneuf to Ottawa during a 2016 trade deadline blockbuster. His goodbye cost the Leafs nearly $5 million against the cap that season, but his $7 million cap hit, which is highest on the team, doesn’t expire until 2021. The Sens managed to move him to the L.A. Kings in early 2018, but were forced to retain 25% of his hefty salary. The Kings bought him out after a season and a half.

THE CANADIAN PRESS/Adrian Wyld

28. Troy Tulowitzki – Colorado Rockies

Troy Tulowitzki and his massive contract was shipped to Toronto in 2015 as the team tried to win a championship. They reached the ALCS in both 2015 and 2016, but couldn’t crack the Royals or the Indians to get to the Fall Classic. As for Tulo, he has only shown glimpses of being the perennial All-Star he was while playing in Colorado, and his reputation for being made of glass was solidified. In hindsight, the Rockies offloaded this massive contract at just the right time.

Tulowitzki is still being paid the second half of a massive ten-year, $157.7 million contract. He made $20 million in 2017, and only appeared in 66 games due to a variety of injuries. He seemed to trip and hurt himself every few weeks. Even when he was healthy, he only hit .249/.300/.378 and managed to strike out in over 15 percent of his plate appearances. He didn’t play at all in 2018, after undergoing surgery to remove bone spurs in both of his heels. He still pocketed another $20 million though. The Jays finally had enough, and cut him loose in December 2018, still on the hook for $38 million in remaining salary.

Tulo promptly signed a one-year deal with the Yankees for the league minimum (remember, Toronto is still paying him for 2019, 2020, and 2021), where he promptly got injured again and sent home to rest.

THE CANADIAN PRESS/Fred Thornhill

27. Albert Pujols – Los Angeles Angels

We’re not here to slag on Albert Pujols. The man is a legitimate Hall of Famer and for a long stretch of his career he was the most feared hitter in baseball. He recently joined the 3,000 hit club (which earned him an extra $3 million) and is sixth on the all-time homerun leader board, with 646 career dingers. If he actually plays out his contract, he could get into the top five by passing the likes of Willie Mays (660) and Alex Rodriguez (686).

The problem is that Pujols signed an obscenely large contract with the Angels back in December 2011 — a ten-year, $240 million deal that would pay him until he was 41-years-old. The contract was back loaded, meaning he actually gets paid more as he ages, which also comes with a decline in production.

Pujols still hits around .245, but he used to hit .330 with relative ease. His slugging numbers are way down too. He used to hit 40 homers a year, but he only managed 23 in 2017 and 19 in 2018. His OPS used to hover around 1.100 (which is massive), but recently has been more like .700. He has battled foot injuries that slowed him down considerably, and his defense at first base (when he’s not in the DH spot) has also dropped. Sadly, no athlete has ever defeated Father Time and Pujols is destined to be his next victim.

The Angels are stuck with him though. His contract will pay him a combined $117 million from 2018 to the end of 2021 and he has a full no-trade clause. If he somehow managed to break the all-time home record, he’ll earn another $7 million. He also has a $10 million “personal services” contract that will be paid out after his playing contract expires. He’s already 38-years-old, and isn’t getting any younger. What were the Angels thinking?

(AP Photo/Mark J. Terrill)

26. Eric Gagne – Milwaukee Brewers

Canadians in major league baseball are still fairly rare. Canadians who do well at the big league level are even more unusual. Montreal native Eric Gagne is part of a collective group of Canucks who had success in the MLB, especially for his monster 2003 season with the Dodgers, when he led the majors in saves with 55 and copped the Cy Young (and a sixth place finish in MVP voting). That great season was sandwiched between two other stellar campaigns, where he save 52 and 45 games for a three-year total of 152.

Injuries would limit Gagne to just 16 appearances between 2005 and 2006, but in 2007, he had a renaissance of sorts with Texas and Boston, posting a 4-2 record in 54 games, with 16 saves and 51 strikeouts in 52 innings. The Milwaukee Brewers thought maybe he was all the way back and signed him to a one year, $10 million contract (despite his name being listed in the Mitchell Report as an alleged HGH user). It would be Gagne’s final season in the Bigs, as he blew seven of 17 save opportunities and had a 5.44 ERA. He was labeled by Brewers’ fans as a “10 million dollar mistake.” At least it wasn’t a multi-year deal.

(AP Photo/Morry Gash)

25. Colorado Rockies – P Mike Hampton

The Rockies actually made two blunders prior to the 2001 season, signing soon-to-be pitching duds Mike Hampton and Denny Neagle. Neagle, though, cost less and actually “out-pitched” Hampton, if truth be told. In any case, Colorado saw two former 20-game winners as signing fodder and then tossed a massive eight-year, $121 million contract in front of good pitch, good hit Hampton.

The thin Colorado air, though, would be anathema to Hampton, who went 14-13 with a lofty 5.41 ERA and career high 31 homers against in 2001. He did redeem himself by hitting seven homers and driving in 16 runs during in limited plate appearances, but that’s beside the point. Hampton was much, much worse in 2002, going 7-15 with a 6.15 ERA and a paltry 74 strikeouts in 178.2 innings. The Rockies unloaded him to Florida at the conclusion of that season as they couldn’t get rid of him fast enough.

(AP Photo/John Bazemore)

24. Homer Bailey – MLB

Homer who? Cincinnati Reds righthanded starter Homer Bailey had one of the largest active contracts in baseball among pitchers, at $105 million for five years when he signed in 2014. And just what, pray-tell, did David Dewitt “Homer” Bailey, Jr. do to merit such an outlay of cash from perennially thrifty Cincinnati? Not a whole lot, in our estimation. He has never been an All-Star or had his name mentioned in any Cy Young conversation so far in 13 big league seasons.

In the two years preceding the fat contract award, Bailey did pitch over 200 innings in each and had an overall record of 24-22 and an ERA north of 3.50. In the first year of the pact, 2014, Bailey went 9-5 and had to pack it in after just 23 starts with arm fatigue — which means a physical wasn’t done correctly before ink was spilled on that pact. That arm fatigue didn’t get any better and then in 2015 he had to have Tommy John for a torn UCL, limiting him to just two starts.

He didn’t make another start for nearly a year, taking the mound on July 31, 2016 and finishing that campaign with a 2-3 record in six starts, with a 6.65 ERA. He missed the first part of the 2017 season and when he did make it back in, Bailey was 6-9 with a 6.43 ERA. The next year, 2018, wasn’t much better, although he did make 20 starts (but went 1-14 with a 6+ ERA again). Bailey was traded to the Dodgers in the winter, who promptly released him the same day. He signed a league minimum contract with the Royals, but will still get $22+ million in 2019 from his previous employer.

(AP Photo/John Minchillo)

23. Mike Conley, Jr. – Memphis Grizzlies

Veteran point guard Mike Conley Jr. was an excellent defender playing on a good but not-yet-great team in Memphis. Also a good three point shooter (37.5 percent effective, career) Conley has the distinction of signing the biggest NBA contract in total dollars (at the time), for $152 million over five years, which he inked in 2016. Others have surpassed it since, but it was eye-popping back then. And still it.

We thought that kind of dough was reserved only for superstars like James Harden and Stephen Curry. Apparently, slightly better than average floor generals qualify too. Now 31 and with 12 seasons under his belt, we have concerns. Injuries took their toll in 2017-18, limiting Conley to just 12 games. He bounced back in 2018-19, posting career highs in points and rebounds. Just good enough to be traded to the contending Utah Jazz in the summer of 2019, who will have to pay him up to $66 million over the next two seasons as the miles continue to pile on.

(AP Photo/ Evan Vucci)

22. Steven Gerrard (L.A. Galaxy)

Stevie G was (and still is) a Liverpool legend after spending almost his entire career playing for the Reds in Mersyside. He started to slow down as he approached his mid-30s, as most players do. After all, those legs had a ton of mileage on them from carrying Liverpool to FA Cup wins in 2001 and 2006, and a famous Champions League victory in 2006 (but zero Premier League titles, as opposing fans are quick to point out). He also had a long career in the midfield of the England National Team, although they failed to win any major intentional silverware.

In 2015, Gerrard left Liverpool and followed in the the footsteps of fellow Englishman David Beckham by signing for the L.A. Galaxy on an 18-month designated player contract, reportedly worth as much as $9 million. In that season and a half, the Galaxy made the playoffs twice but failed to make it back to the MLS Cup. Gerrard was often ineffective on the field, scoring just five goals in 34 appearances for the West Coast club. He decided to retire at the end of his contract, saying that the long away trips, changes in elevation, and diverse weather across North America made it hard for him to adapt to the league. He was an average, if not a little slow, midfielder while with the Galaxy, and certainly not worth the $9 million he was paid. Probably sold some shirts though.

(AP Photo/Jae C. Hong, File)

21. Mike Richards – Philadelphia Flyers

The Flyers did the deed and the L.A. Kings suffered much of the fallout. In December 2007, the Flyers, undaunted by a little thing called the salary cap, signed Richards to a rich 12-year contract worth $69 million. After all, he was their future captain and like “goalie of the future” Ilya Bryzgalov, the team wanted him around for a while.  Soon though, he and a few others (including teammate Jeff Carter) were accused of being boozy nighthawks, which didn’t sit well with Richards. Flyers management must have believed the press and shipped him out just and a half years after the contract award.

The Kings, who gave up Brayden Schenn and Wayne Simmonds in the deal, must not have been reading Philly newspapers back then. Richards, not a great skater to begin with, skated even slower in L.A. and his production tailed alarmingly. His best season, 2008-09 with the Flyers, he had 80 points, and his first season in La-la land he had just 44. By 2014-15, he was was down to 16 points in 53 games and plodding along at -10. A drug bust and suspension followed, as did a buyout. The Kings are still pay Richards a quarter million a year until 2031-32 as per the buyout agreement.

(AP Photo/Chris Szagola, File)

(AP Photo/Chris Szagola, File)

20. Marian Gaborik – Los Angeles Kings

It was a tough choice between former Stanley Cup heroes Dustin Brown and Marian Gaborik , but in the end we went with the old(er) guy. While Brown carries a cap hit of $5.875 million until 2022, he’s enjoyed a renaissance of sorts and put up 61 and 51 points, respectively, in the last two seasons.

Gaborik, who was huge in the Kings last Stanley Cup run in 2014 when he had 14 goals in 26 games, missed huge chunks of time due to injuries and really hasn’t been a boon to the team’s offence since. His production dipped to a career low 21 points in 2016-17, and he matched that mark in 2017-18. Now 37-years-old and playing in Canada after a trade to Ottawa in early 2018, he is still owed the end of the seven-year, $34 million contract that pays him until the end of 2021. He also missed the entire 2018-19 season after back surgery, so a late-career resurgence looks next to impossible.

(AP Photo/Chris Carlson)

19. Milan Lucic – Edmonton Oilers

The Oilers could be forgiven for signing tough-as-nails playmaker Milan Lucic to a rich, seven-year, $42 million contract in 2016. After all, he had plenty of playoff experience, had won a Stanley Cup and his services were in huge demand. The team, with Lucic in the line-up, made the playoffs for the first time in a long time and went two rounds into the post-season before succumbing.

Lucic was good in that first season, scoring 50 points in 82 games, earning his $6 million cap hit, for the most part. The next two years, though, has Oilers fans scratching their heads. Lucic posted just 34 points in 2017-18 and then just 20 the following campaign.  He went from posting +/- numbers in the positive double digits to scoreing -12 and -9. Beyond that, Edmonton has failed to make the playoffs for two straight seasons, even with Connor McDavid being the best player on the planet. Now that McD’s massive contract extension has kicked in, paying him $12+ million a year, Lucic’s cap hit of $6 million until the end of the 2022-23 season hurts even more.

THE CANADIAN PRESS/Jason Franson

18.   Barry Zito – San Francisco Giants

On December 29, 2006, Barry Zito signed a historic deal with the San Francisco Giants, a seven-year pact worth $126 million, plus an $18 million option for 2014 with a $7 million buyout. At the time, Zito’s contract was the most for any pitcher in MLB history. The Giants saw a 28-year-old inning eater (six straight years of 200+ innings) and Cy Young winner (he was 23-5 in 2002) and lured him across the bay from the Athletics.

The Giants, sadly, would never get 200 innings out of Zito in seven seasons and would see his ERA balloon from 3.83 in 2006 with Oakland to 5.15 in 2008. He posted a 63-80 record and a 4.62 ERA in 197 starts and for the Giants between 2007 and 2013, after going 102-61 with Oakland. The Giants declined the option in 2014, which is still payable in installments with 1% interest tacked on each year through 2020. His only saving grace was a win for the champion Giants during the 2012 World Series.

(AP Photo/Jeff Chiu)

(AP Photo/Jeff Chiu)

17. Ryan Howard, Philadelphia Phillies

Ryan Howard quietly slipped away from baseball in 2016, hitting a horrible .196 with 25 homers, just four years removed from signing a lucrative five-year, $125 million deal with the Phillies prior to the 2012 season. The 2006 NL MVP and power hitter was coming off his sixth straight year of finishing among the top ten in National League MVP voting when he signed the extension of his dreams at age 32. It has been all downhill since.

Between 2012 and 2013 he missed 173 games and saw his average numbers tumble across the board. He rebounded in 2014 to hit 23 homers and 95 RBIs, but led the National League in strikeouts for the second time in his career with 190, while batting a dismal .223 and slugging just .380. In 2015, the albatross of that contract loomed larger, with his RBI total falling by 18. His defense, or lack thereof, went from “just okay” to “terrible” in 2016, when he made 11 errors on just 613 chances. Coupled with his tepid bat, it hastened his departure.

(AP Photo/Chris Szagola)

(AP Photo/Chris Szagola)

16. Ilya Kovalchuk – New Jersey Devils

We have said a few times that Ilya Kovalchuk should still be playing in the NHL. Just not at the money he was making when he left. One of the most talented and enigmatic scorers the league has ever known certainly stiffed the New Jersey Devils before bolting to Russia. The contract he signed in 2010 was as contentious as it was ludicrous. Already 27 and without much of a post-season resume, Lou Lamoriello and the Devils tried to circumvent the salary cap with an insane 17-year, $102 million deal.

Now, we’re not talking Alexei Yashin here, but the term seemed out of this world and the NHL agreed. The deal was lowered to a still eye-rolling 15 years and $100 million. Plus it cost the Devils draft picks and a fine from the NHL (both later rescinded or rolled back, in the case of the money). Kovalchuk lasted just three seasons — two and a half if you don’t count the lockout shortened 2012-13 — under his new deal, playing in 222 games and scoring 201 points. When play in the NHL resumed, Kovalchuk decided to stay in Russia anyway.

In 2018, the reclusive Russian attempted a comeback in the NHL. He signed a three-deal to play with the Kings, and scored just 34 points on a dreadful L.A. team.

AP Photo/Jason DeCrow, File

AP Photo/Jason DeCrow, File

15. Bobby Bonilla – New York Mets

For a while in the major leagues, former New York Mets slugger Bobby Bonilla was the highest paid player in baseball, making about $6 million a season in the early 1990s. Not too shabby for a guy who’s all-time high in homers was 34 and was an All-Star just six times in 16 seasons. But, in 2000, the Mets owed Bonilla $5.9 million, but his production was so paltry they had no choice but to get out from under that millstone of a deal. So, what did they do to alleviate the strain on their cash flow.

They agreed to make deferred payments, in the amount of $1.19 million per year, until 2035. Yes, you did hear us correctly! 2035! How bad are the optics, then, on this deal? Well, consider that the Mets paid Bonilla more than the combined salaries of their flame-throwing young pitchers Jacob deGrom ($556,875) and Noah Syndergaard ($507,500) back in 2015, and roughly equal amounts again in 2016. We’re not mathematics geniuses or anything, but when Bobby turns 72 in 2035, he’ll have been paid almost $30 million to be bought out of a $5.9 million contract. Yikes!

Source: usatoday.com

Source: usatoday.com

14. Michael Vick – Philadelphia Eagles

Michael Vick, early in his career, had oodles of talent, but cement for brains. How else to describe the vicious and not-very-well-thought-out choice to run a clandestine dog-fighting ring, when most of America reviles a dog abuser worse than a domestic abuser. Once he left prison, Vick’s early contracts reflected his status as a pariah —  short one-year deals with no guaranteed money. But, he was able to resurrect his career enough that the Philadelphia Eagles were prepared to compensate him handsomely. Too handsomely, in hindsight.

A six-year, $100 million contract in 2011 for a 31-year-old convicted felon was way, way too dumb for words. Yes, he had a fine season in 2010 and went to a Pro Bowl, but not long after that, his production declined badly (from 21 TDs and six INTs in 2010, to 18 and 14 in 2011). By 2013, he’d worn out his welcome in Philly and was gone to the equally inept New York Jets. The kicker of the contract is that $40 million was guaranteed. But, then again, this is the Eagles we’re talking about.

AP Photo/Ben Margot

AP Photo/Ben Margot

13. CM Punk – UFC

UFC guru Dana White never met a marketing opportunity he didn’t like, but with the multi-fight deal (rumored at eight but so far only two) he threw at CM Punk — aka Phillip Brooks — we think he’s finally lost his marbles. It’s not that Punk isn’t marketable or maybe even tough, but the dude was 37 when he made the switch from WWE to MMA, and had only been training for a short time.

The move to bring in Brooks was met with howls of disapproval across the MMA scene, with many fighters calling him out right away. Nate Diaz said simply, on Twitter, “why?” Alp Ozkilic tweeted, “I hope CM Punk realizes that ufc is actually real fighting. Lol”

Bringing Brock Lesnar into the fold was a fairly successful venture while it lasted, but even White himself wasn’t quite certain that Punk will have any staying power. “He could be one and done, or he could have a career here. I don’t know. We’ll see,” White said. Notice he said “one and done” first? Punk’s first UFC fight was a shameful defeat to novice youngster Mickey Gall. He lasted longer in his second try, but lost a lopsided decision to Mike Jackson in June 2018. He probably won’t get another shot in the UFC, especially now that he’s over 40.

Jim R. Bounds/AP Images for WWE

Jim R. Bounds/AP Images for WWE

12. Colin Kaepernick – San Francisco 49ers

We have been critical of the NFL for blackballing the controversial Kaepernick — really, he should be a back-up somewhere, at least. However, the six-year, $126 million contract ($54 million guaranteed) he signed with San Francisco in June 2014 rates as monumentally short-sighted. He was coming off a pretty good 2013 season, his first full campaign after going to the Super Bowl after the 2012 campaign, recording a 12-4 record with 3,197 yards passing, 21 TDs, and eight interceptions. He added another 576 yards passing in three playoff games.

However, he wasn’t even a Pro Bowler and wasn’t given consideration for offensive player of the year or MVP. The deal he signed was just $1 million shy (yearly) of a pact given to great QB Aaron Rodgers, who signed his the same year. And Kaepernick’s contract was for six year versus Rodgers’ five. The first year of his deal, he was adequate, then it sunk to back-up level performance by 2015 and controversy-stoked mediocrity in 2016. He opted out of his deal after the 2016 season, perhaps foolishly, and hasn’t played since.

(AP Photo/Marcio Jose Sanchez, File)

11. Frank Lampard – New York City FC

Remember the Steven Gerrard section? Basically, you can copy and paste it down here for Frank Lampard’s time in MLS. They arrived at the same time, left at the same time, were both England greats, and spent many impressive years with a big English club. At least Lampard actually won the Premier League with Chelsea though, right?

In his defense, Lampard actually got on the scoresheet a lot for New York City — 15 goals in 31 appearances. The real problem with Lampard in MLS came down to two factors, that are obviously tied together: his age and his health. He was already 36 when he arrived, with plenty of miles on his legs after more than a decade of midfield grinding for Chelsea. Nagging injuries were definitely catching up to him. The final blow for Lampard in New York was when Toronto FC dismantled City 7-0 on aggregate in the 2016 playoffs, with Frank playing both legs and failing to make an impact. Those were the last professional games of Lampard’s career.

(AP Photo/Craig Ruttle, File)

10. Roberto Luongo – Vancouver Canucks

Bobby Lu was once a great NHL goalie, earning All-Star nominations and often finishing in the top five of Vezina Trophy voting. As he got older, though, the nagging injuries become more and more pronounced. Before that, though, the Canucks signed Luongo to a 12-year, $43 million contract extension. The contract was front-loaded, at least, helping alleviate the troubles that the more common back-loaded deals come with. Even so, he’s going to get paid until he’s 43 — the end of the 2021-22 season. Oh, and he just retired.

The Canucks somehow unloaded the contract on the Florida Panthers via a trade in 2014. Luongo even has some solid seasons in the Sunshine State, but that contract remains a stinker. To make matters worse, the Canucks will now get hit with an additional salary cap penalty because their former goalie retired before the end of his contract — a full five years after they traded him away!

(AP Photo/Bill Kostroun)

9. Alexei Yashin – New York Islanders

The Islanders just recently stopped paying Alexei Yashin $2.2 million dollars a year in dead money, the last payment of which was sent out in 2015. That was a full eight years after he last played for the Isles! Yashin was the No. 2 overall selection in the 1992 NHL Entry Draft, and did register a couple of 40-goal seasons in his time with Ottawa before being dealt to the Islanders on draft day in 2001.

The contract he signed was actually pre-salary cap era (10 years and $87.5 million in 2001) and wasn’t terrible based on his production, but the terribly enigmatic player would sometimes disappear in games, especially the ones that mattered. The buyout, which was negotiated under the terms of the new CBA (thus post-salary cap) netted Yashin roughly $17.63 million, at which point he packed his bags and took off for the KHL, only playing half of the agreed term but walking away with oodles of cash regardless.

(AP Photo/Kathy Willens)

(AP Photo/Kathy Willens)

8.   Prince Fielder – Detroit Tigers

In 2012, the Detroit Tigers signed the portly Fielder to a nine-year, $214 million contract, which is still one of the richest deals ever made in sports. In the short term, it seemed like money well spent, as Fielder hit 228 homers and drove in 646 runs in six seasons with Milwaukee between 2006 and 2011 to earn the massive payday. Fielder did hit well during his two seasons in Detroit, but his post-season numbers left the Tigers cold, leading to a trade following the 2013 season.

He had a .071 batting average in a World Series sweep at the hands of the San Francisco Giants in 2012, only to follow that up with an equally dismal turnout in the 2013 playoffs, when he hit .182 in the ALCS against Boston with no homers and no RBIs. Fielder faded in the worst possible way and was dealt immediately following the season, with the Tigers having to eat $30 million in salary. Fielder faded badly in Texas, with the 2015 All-Star season being the lone bright spot. As for his lone post-season appearance with Texas, the 2015 ALDS against Toronto, he hit .150, with one RBI. He hit just .212 in 89 games in 2016, and was forced to quit baseball due to serious neck injuries. He didn’t officially retire though, because he can collect the rest of that cushy deal until the end of 2020. He’ll make $36 million to sit at home and “rehab.”

(AP Photo/LM Otero)

(AP Photo/LM Otero)

7. Carl Crawford – Boston Red Sox

What is it about former Tampa Bay Rays who flounder once they leave Florida? In December 2010, Crawford had just come off a fourth All-Star campaign in nine seasons, along with his first Gold Glove and Silver Slugger awards. The triples and base stealing machine (he led the AL in those categories four times each) became a free agent and cashed in with the Boston Red Sox in late 2010, to the tune of an astounding $142 million over seven years.

It must have been a great Christmas gift for the outfielder, who then went on to struggle in 2011, batting just .255 (after a .307 season in 2010) with 18 stolen bases after swiping 47 in 2010. He would play all of just 31 games in 2012 and have season-ending Tommy John surgery. He was subsequently traded to the Dodgers and added fuel to an unhappy chorus about his play by calling Boston fans “toxic.” He enjoyed a bit of a renaissance with the Dodgers in 2013-14, but the injury bug bit again and his numbers declined precipitously in the last two seasons of his career, which ended after just 30 games (.185 batting average) in 2016. Still got paid though.

(AP Photo/Ross D. Franklin)

(AP Photo/Ross D. Franklin)

6. Kimbo Slice – Bellator MMA

The late Kimbo Slice fought just twice after signing a lucrative five-year deal with Bellator MMA in January of 2015. He won his first bout, but at the expense of 51-year-old Ken Shamrock. Yeesh, Shamrock is closer to senior’s discounts than he is to his prime, so what in the name of Kenneth Allen (you can Google this one) was Slice doing fighting him? Probably had something to do with the fact that a then-36-year-old Slice lost to Matt Mitrione his last time out in 2010. A 2016 fight with Dada 5000 (look, Bellator is a weird place) was originally a TKO victory for Slice before it was overturned into a No Contest when Slice failed a PED test.

All together, Slice’s record in MMA was 5-2 (1), hardly the stuff of multi-year, multi-million dollar contracts. The fight with Shamrock, predictably, was met with heaps of scorn and derision on Twitter. One Tweeter nailed it right with “Kimbo Slice vs Ken Shamrock with the co- main event Rocky vs Ivan Drago!” Ron Burgundy on MMA (@RonBurgundy_MMA) said it best, “Kimbo vs. Shamrock gonna be fiya y’all. Winner gets a senior discount at Golden Corral.”

Slice was originally going to get a rematch against James Thompson, but passed away suddenly at the age of 42 in 2016.

THE CANADIAN PRESS/Neil Davidson

THE CANADIAN PRESS/Neil Davidson

5. Nicolas Batum – Charlotte Hornets

We don’t begrudge low-key French National Nicolas Batum making a living in the NBA. However, he owns a ridiculous deal, at $120 million over five years, which he signed in 2016. The Charlotte Hornets swing man is an excellent defender and decent three-point shooter, but from a purely statistical point of view, is he worth $24 million average per year? Not when better and more accomplished players like Kyrie Irving, Kawhi Leonard, and Jimmy Butler were making considerably less on average.

Batum is a nice piece of a fairly mediocre team that has made the playoffs just once in his four years there, bowing to the Miami Heat in the first round of the 2015-16 season. Batum has never led the league in any one statistical category and has never been an All-Star, yet gets paid like one. $120 million is a lot of dough for a guy who averages 11.8 points and 5.3 rebounds per game.

(AP Photo/Rich Pedroncelli)

4. Jay Cutler – Chicago Bears

We’re not certain what the Chicago Bears braintrust was thinking in early 2014, but they were clearly having an episode of fantasy when they signed average quarterback Jay Cutler to a way-above-average seven-year, $126 million contract. In terms of all total value contracts signed by quarterbacks at that point, it was the fourth largest, ever. All that cash, for a surly guy who threw for over 4,000 yards just once, his Pro Bowl year with Denver in 2008.

Otherwise, his career numbers are less than inspiring. He has thrown 227 touchdown passes, but also 160 interceptions, 48 of them in the 49 games he’s played since put his John Hancock on that outrageous contract. Other than one Pro Bowl, the only categories that the slow-footed Cutler has led the league in are interceptions (twice) and sacks (52 in 2010). Little wonder the Bears opted out of that deal in early 2017, exercising a $2 million buyout clause. The Dolphins gave him a shot in 2017 (for much less money), but another losing season followed.

(AP Photo/Wilfredo Lee)

3. Rafa Marquez (New York Red Bulls)

Typically speaking, Designated Player contracts in MLS are most often used on attacking players. Defense might be important, but goals win games. There’s a good reason that more DP contracts are given out to offensive players than defensive players. One of the biggest exceptions to that rule was Rafael Marquez, the Mexican international centerback who joined the New York Red Bulls in 2010. He signed a three-and-half-year contract with the club that was worth big bucks, but never lived up to it.

Marquez’s time in New York was marred by criticism from both the fans and the media. He was often injured. When he did play, he was prone to foolish red cards that resulted in missing further games due to suspensions. In short, it didn’t look like Rafa really cared about his effort, the team’s results, or the critics harsh words — as long as those big DP paychecks didn’t bounce. Marquez would later trash the league entirely, telling ESPN Deportes that coming to MLS was a “bad decision” and perhaps the worst decision of his entire career. He claimed to regret turning down offers from European clubs, including Juventus. Red Bull fans regret it, too.

(AP Photo/Rich Schultz)

2. Rick DiPietro – New York Islanders

This is the grand-daddy of all bad contracts and one that would probably be in the curriculum if there was a course on how to be a sports GM. In the 2006-07 season, the New York Islanders’ somehow decided it would be a great move to sign a goalie who had never recorded an NHL save percentage of .915 or better to a whopping 15-year deal. The pact given to Rick DiPietro was for a whopping $67.5 million, easily the least prescient and later deemed dumbest contract ever awarded in the NHL — possibly in all of pro sports.

DiPietro was injury riddled and inconsistent and had barely played two full seasons worth of games across six years after being selected No. 1 overall out of Boston University in 2000. For his entire career, he played a grand total of 318 NHL games and logged a pretty pedestrian .902 save percentage. He was finally bought out of his deal and tried (but failed) in a AHL tryout with the Carolina Hurricanes organization in 2013-14.

(AP Photo/Kathy Kmonicek, File)

(AP Photo/Kathy Kmonicek, File)

1. Alex Rodriguez, NY Yankees

It must have chuffed the egotistical Rodriguez that Miami’s Giancarlo Stanton inked a deal that dwarfed his own massive contract by $50 million. And it’s ironic now that Stanton is a Bronx Bomber. Don’t get us wrong, the three-time MVP A-Rod will surely go down as one of the top third basemen/DH the game has known (with an asterisk forever attached because of alleged PED use). But that astronomical 10-year, $275 million pact he signed in 2008 slowly became the albatross of albatrosses around Yankees management’s neck.

He took a lot of grief for bad years in 2011 and 2012, rightly so, hitting just 34 total homers and then playing just 44 games in 2013 before being punished severely by MLB for his steroid use and missing a whole season through suspension. The 33-homer campaign of 2015 was a one-off, especially after he hit .200 in 65 games during the 2016 season, with nine homers. He didn’t get quite the self-congratulatory retirement tour he probably envisioned, slowly phased out in the waning months of 2016. Of course, he still got paid to the bitter end.

(AP Photo/Patrick Semansky)

(AP Photo/Patrick Semansky)