A fool and his money are soon parted.

In the case of big league sports team owners and league executives, the sky never seems the limit when awarding monster contracts to men playing kids’ games.

We’ve covered them all here, but as usual, there is never enough space to get all the egregiously bad contracts under one banner.

From Alexei Yashin’s idiotic deal to New York Islanders’ teammate Rick DiPietro’s ill-advised pact, we’ve given the NHL it’s due. Over in major league baseball, the insane money given to A.J. Burnett is well documented and we won’t touch A-Rod’s millions. Listing all his dirty laundry is like shooting fish in a barrel. The NBA’s Gilbert Arenas and Allan Houston didn’t slip our attention, either.

So, we’ve got 15 disgustingly bad contracts given to athletes who didn’t warrant the big bucks thrown at them and did little to fulfill them. We should all be so lucky. In no particular order.

15. 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 one) 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. It remains to be seen if he’ll get another chance.

Jim R. Bounds/AP Images for WWE

Jim R. Bounds/AP Images for WWE

14. David Beckham – MLS

The media frenzy that Becks started when he announced his departure from AC Milan to the L.A. Galaxy in early 2007 was like nothing ever seen before. Of course, reports generated that his potential contract was worth a whopping $250 million — a huge sum for a past-his-prime superstar. Now, those figures were wildly inflated, but we think the Galaxy and its fans never got the full “Bend It Like Beckham” experience.

Sure, he sold a lot of jerseys and practically re-made the MLS brand for a while, but the salary and other perks didn’t match his performance on the pitch and certainly didn’t make him any more loyal to the league or his team. He definitely didn’t earn the $6.5 million he was paid annually, given that his aging body was breaking down, nor the provision in his contract that could see him purchase a future MLS franchise (he’s still trying to figure out a Miami stadium deal for this one) for just $25 million. He also had a proviso allowing him to opt out of his contract after just three years. Whatever the case, the Galaxy got 18 goals in 98 games (none in the post-season) from Becks, interspersed with lucrative loans to Milan in between. Although he did raise the profile of the league and win two MLS Cups with the Galaxy.



13. Ilya Kovalchuk – NHL

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 $102 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 195 games and scoring 174 points. So, it wasn’t the (sort-of-declining) production you could sneer at, just the typical lack of loyalty from a superstar player.

AP Photo/Jason DeCrow, File

AP Photo/Jason DeCrow, File

12. 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.



11. Bobby Bonilla – MLB

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 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 this year alone, Bonilla will rake in more than the combined salaries of the Mets’ flame-throwing young pitchers Jacob deGrom ($556,875) and Noah Syndergaard ($507,500). We’re not mathematics grads here, 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

10. Michael Vick – NFL

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 18-14 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

9. Homer Bailey – MLB

Homer who? As of this writing, Cincinnati Reds righthanded starter Homer Bailey has the 13th largest active contract in baseball among pitchers at $105 million for five years, signed in 2014. It is also tied for 114th richest among all sports league contracts (for total value). 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 in 11 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. He still two years left on his deal.

(AP Photo/John Minchillo)

8. Colin Kaepernick – NFL

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 contract 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 then, was just $1 million shy (yearly) of a pact given to a great QB, Aaron Rodgers signed the same year (he was making $22 million average to Kaepernick’s $21 million). And Kaepernick’s contract was for six year vs. 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.

(AP Photo/Marcio Jose Sanchez, File)

7. Vernon Wells – MLB

The Toronto Blue Jays haven’t made it a habit of handing out massive contracts, but the one they gave Vernon Wells at the end of the 2006 season made little sense. His seven-year, $126 million contract is 12th biggest all-time among MLB outfielders. He was a two-time All-Star and three-time Gold Glover at that point, but he peaked too soon. 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 pedestrian 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.

(CP PHOTO/Adrian Wyld)

6. Nicolas Batum – NBA

We don’t begrudge low-key French National Nicolas Batum making a living in the NBA. However, he owns the 17th biggest deal in the NBA, at $120 million over five years, 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 are making considerably less on average per season. Batum is a nice piece of a fairly mediocre team that has made the playoffs just once in his three years, 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.

(AP Photo/Rich Pedroncelli)

5. Jason Heyward – MLB

By our estimation, excellent defensive outfielder Jason Heyward has had one outstanding season. That would have been 2012 with Atlanta, when the five-time Gold Glover had his best year at the plate, too, hitting .269 with career highs in homers (27), doubles (30), triples (6) and RBI (82). Two teams and one enormous contract later, Heyward isn’t among the leaders in any category other than defensive. He had a decent season in 2015 with St. Louis, causing the rival Cubs to go into spasms when he became available in free agency. They threw eight years and $184 million at him to sign, tying him for 17th on the all-time large total contracts list. And he struggled mightily during that magical 2016 season, a championship hiding his glaring inconsistency at the plate (.230 average, 7 HR, 49 RBI). He’s been near invisible in two playoff seasons too, hitting just .107 in 24 games (7-for-65), with just one RBI.

(AP Photo/David Banks)

4. Shea Weber – NHL

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 has shown the cracks of age this year and is now on the DL for a while in a Habs season gone horribly wrong (while PK thrives 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. Not including this season, Montreal will pay him a sliding scale of $6 million for the next four seasons, then $3 million for one and $1 million for three. That is, unless they can find a way to deal him and his fat pact elsewhere.


3. David Price – MLB

The Toronto Blue Jays, along with several other teams, lost out in the David Price sweepstakes during the 2015 off-season. However, they may be breathing a sigh of relief now. Obtained at the trade deadline that year, Price was stellar in helping propel the Jays to their first playoff appearance in 22 years. He seemed to relish his time in the Big Smoke, but when crunch time came, dollars-wise, the 2017 Cy Young winner bolted for astronomical dollars in Boston. It was worth the eye-glazing sum of $217 million over seven seasons. Thing was, though, Price was already 30 and while he was a workhorse regular season hurler, had and still has a reputation for being a mediocre playoff performer (2-8 record in 17 games, 5.03 ERA, 1.214 WHIP). He had a decent year in 2016, but a nagging elbow injury in 2017 limited him to just 11 starts. We think his contract, which doesn’t run out until 2022 (when he turns 37), will be an albatross around the necks of Bosox management, sooner than later.

(AP Photo/David Goldman, File)

2. Mike Conley, Jr. – NBA

Like Nicolas Batum over in Charlotte, veteran point guard Mike Conley Jr. is an excellent defender playing on a good but not yet great team in Memphis. Also a good three point shooter (37.7 percent effective, career) Conley has the distinction of owning the sixth-biggest NBA contract (in total dollars) at $152 million for five years, which he inked in 2016. And, at the time he signed it, it was the greatest contract by total value in NBA history. And here 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 30 and in his 11th season, injuries are taking their toll and with the Grizz struggling along near the bottom of the Western Conference standings, his fat contract looks worse every day.

(AP Photo/ Evan Vucci)

1. Jay Cutler – NFL

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 QB Jay Cutler to a way-above-average seven-year, $126 million contract. In terms of all total value contracts signed by quarterbacks to this point, it remains 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.

(AP Photo/Wilfredo Lee)