Sports is a business and trades are just part of life for athletes.

Inevitably, if a star athlete’s worth is still of some value, they can be dealt in a heartbeat.

In the Big 4, many a trade has worked out for the better, while some swaps just get filed under “huh?”

The NFL may not be the leader in swaps — the league doesn’t have a “deadline” — but there have been quite a few off-season and draft day deals that set tongues wagging and fingers flying among learned pundits.

Often, the most spoken about dubious deals are ones like San Diego’s draft day trade to get Ryan Leaf and Atlanta giving away Brett Favre to Green Bay for virtually nothing.

We’ve trod that ground pretty well. There are several other deals that may have been forgotten over the years, or recent transactions whose impact is still being felt today.

Here are 25 NFL trades that backfired miserably on teams who thought they were getting a good return.

25. Cleveland Trades Away Draft Rights To Carson Wentz – 2016

Just try and follow the convoluted trade that Cleveland and Philadelphia made prior to the 2016 entry draft. We dare anyone. What it boils down to is that the Browns — who have eternal problems drafting, keeping and trading for QBs — dealt the rights to one of either future franchise pivot Jared Goff or Carson Wentz to Philadelphia for what really amounts to reserve WR Corey Coleman. In the last 10 seasons, the sorry Browns have used 19 different quarterbacks and the only one left from a recent group that included DeShone Kizer and Robert Griffin III is Kevin Hogan. Yes, the Browns did trade for Tyrod Taylor. Call us in a year to tell us how that worked out. As for Philly trading up to eventually get Wentz, the jury is just taking a break, considering they won a Super Bowl with Nick Foles. Before he was hurt, though, Wentz started 29 games over two seasons and threw for 7,078 yards and 49 touchdowns, against just 21 interceptions. By contrast, the six different pivots Cleveland employed over 32 games between 2016 and 2017 threw for 7,230 yards and 30 touchdowns, along with an ugly 42 interceptions.

(AP Photo/Mark J. Terrill)

24. New York Giants Deal DE Jason Pierre-Paul To Tampa Bay For A Third Round Pick – 2018

Yes, we know the Giants, after a horrible 3-13 season, have to re-stock the cupboard. But, we’re going to call the March 22 trade that sent two-time Pro Bowler Jason Pierre-Paul to Tampa Bay a prohibitive backfire. Still just 29, Pierre-Paul started all 16 games last season and recorded his highest number of sacks (8.0) since 2014, when he had 12.5. He has 58.5 sacks in his career, 13 forced fumbles, 47 passes deflected and two interceptions in 111 games. All Tampa had to do to get sack master Pierre-Paul was give up a 2018 third round pick and swap their own 2018 fourth rounder for New York’s. Historically, the Giants haven’t done all that well with third round picks. The only defensive lineman they have drafted in the third round in recent memory who has actually stuck around is back-up DT Jay Bromley, who has had two sacks in his career since being picked 74th overall in 2014.

(AP Photo/Steven Senne, File)

23. New Orleans Trades Eight Draft Picks To Washington For Chance To Pick Ricky Williams – 1999

All that success Mike Ditka had with Da Bears in the 80s must have gone to his head. Why else, then, would he trade all his 1999 draft picks with the Saints to Washington for the right to take Texas stud running back Ricky Williams? Williams ran for 884 yards in his rookie season, with two TDs in 12 games. While that’t not bad, the Saints were a dismal 3-13 and Ditka got canned at the end of the year. Williams hung around for two more seasons, where he did rush for over 1,000 yards each time, but the Saints ended up trading him to Miami in 2002, for, wait for it, four draft picks. As for all the picks ‘Nawlins dealt away to Washington, the Redskins made out pretty good after further deals. They would eventually pick Pro Bowl DB Champ Bailey and Pro Bowl LB LaVar Arrington. Not bad.

(AP Photo/Mark Lennihan)

22. Detroit Lions Send LB Kyle Van Noy To New England For Sixth Round Pick – 2016

To us, the deal that Detroit made with New England made no sense at all, especially after the 2017 draft. On Oct. 25, 2016, the Lions traded four-year veteran LB Kyle Van Noy, along with a 2017 7th round draft pick, to the Patriots for a 2017 6th round selection. At that time, Van Noy had started all seven games of the 2017 season and had 23 tackles. He sat out the first two games of his tenure in New England and once he got in, registered 18 tackles, a sack, his first career interception and two pass deflections. And, he had seven tackles and a half sack in the Pats run to the Super Bowl. As for that player Detroit drafted in the six round, QB Brad Kaaya, well, he was cut by them twice and is now on the Indianapolis Colts practice squad. Van Noy rubbed a little more salt in the wounds in 2017, starting 13 games and recording 73 tackles, 5.5 sacks and two pass deflections. Those 5.5 sacks represent two more than were registered all six linebackers on the current Lions depth chart in 2017.

(AP Photo/Adrian Kraus, File)

21. Chicago Bears Deal First Round Pick To Seattle For QB Rick Mirer – 1997

In the rich tradition of Notre Dame Fighting Irish football there have been many great quarterbacks, some of who went on to outstanding NFL careers like Paul Hornung, Joe Theismann and Joe Montana. Then there was Rick Mirer, who looked like he was going to be a player in the early 1990s. He was a standout at South Bend, good enough to be drafted second overall by the Seattle Seahawks in 1993. But, after a pretty good rookie campaign, his game slowly started to deteriorate and on Feb. 18, 1997, the Seahawks packaged him up with a fourth round pick in the 1997 draft for Chicago’s first round selection (which was later packaged up for Atlanta’s first pick, which happened to be third overall). With that pick, Seattle took Pro Bowl CB Shawn Springs, who would play seven seasons for Seattle, registering 20 interceptions, 367 tackles, 1.5 sacks and 27 pass deflections. As for Mirer, he signed a three-year, $11.4 million contract with Chicago, played all of seven games and was gone after the ’97 campaign. Pretty much a bust, overall.

(AP Photos/Gary Stewart, File)

20. New Orleans Swaps WR Kenny Stills For Miami LB Dannell Ellerbe And Draft Pick – 2015

We think the Saints only scratched the surface of former Oklahoma wideout Kenny Stills’ talent. After being drafted way down at no. 144 by ‘Nawlins in 2013, Stills gave the team great bang for the buck, making 17 starts in 31 games over two seasons and catching 95 passes for 1,572 yards and eight touchdowns. However, the Saints deemed him expendable and on Mar. 12, 2015 he was traded to Miami for LB Dannell Ellerbe and a third round pick in 2015 (turned into DB P.J. Williams). After a so-so campaign in 2015, Still has blossomed into a bona fide starter, catching 127 passes in 48 games for 2,013 yards and 18 touchdowns. And, things should only improve for Stills in 2018 with the impending return of QB Ryan Tannehill. Ellerbe started 12 of 15 games he played in New Orleans and had 68 tackles and four sacks. The jury is still out on Williams a reserve corner who has had injury problems and unspecified disciplinary issues that have kept him out of the line-up and/or a regular starting job since being drafted.

(AP Photo/Wilfredo Lee)

19. Green Bay Acquires QB John Hadl From The Rams For Five Draft Picks – 1974

File this one under “it seemed like a good idea at the time.” In 1974, the Green Bay Packers were off to a 3-3 start and then coach Dan Devine thought a change at pivot would be just the tonic to get the team to the playoffs and maybe another Super Bowl. So, they put five draft picks on the table for the Los Angeles Rams (two first rounders, two second rounders and a third) for aging six-time Pro Bowl QB John Hadl, who was already 34. Hadl would pass for just 1,072 yards in eight games (six starts) with three TDs and eight interceptions as the Pack finished 6-8 and out of the playofss. After a miserable 4-9 record (six TDs, 21 INTs) in 1975, Hadl was gone. The Rams, meanwhile used that load of draft picks to take players they would use to dominate the NFC West for years, culminating in an appearance in Super Bowl XIV. The Packers, meanwhile, would stink out the joint for many years after.


18. Oakland Sends Draft Pick To Houston for QB Matt Schaub – 2014

The Raiders must have been awful desperate after yet another 4-12 season in 2013. Why else would they send anyone, whether a roster player or draft pick, to Houston for declining former Pro Bowl QB Matt Schaub? There were plenty of cheap free agent options available to carry the load while they developed a starter — who would be second round pick Derek Carr. Thus, the Raiders sent a sixth round pick to Houston for Schaub, who set a record in 2013 for throwing a pick-six in four consecutive games and who lost the starting job to Case Keenum. And instead of starting for the Raiders in 2014, he was benched in favor of Carr and threw all of 10 passes in 11 games. He completed five of them for 50 yards and had two interceptions (no TDs.). That sixth round pick turned into RB Alfred Blue, who has been pretty darned good for a 181st overall pick, starting 14 of 56 games in four seasons, with 1,908 rushing yards, 316 receiving yards and eight TDs.

(AP Photo/Tom Gannam)

17. Raiders Get Carson Palmer from Cincinnati for Two Draft Picks – 2011

Let’s just say the Oakland Raiders checkered past involved a lot of knee-jerk moves for starting quarterback help. Two seasons before getting a deteriorating Matt Schaub from Houston, the Raiders found themselves without a starter after Jason Campbell sustained a season-ending injury six games into the 2011 campaign. Over in Cincinnati, the Bengals were at an impasse with then two-time Pro Bowl QB Carson Palmer. He threatened to retire if the moribund team didn’t trade him, which led to the team using Andy Dalton, who posted a 6-2 record in 2011 while Palmer sulked. On Oct. 18, 2011 the Bengals dealt him to Hue Jackson and the Raiders for a first round pick in 2012 (CB Dre Kirkpatrick) and a second rounder in 2013 (RB Giovani Bernard). While his passing stats wouldn’t be all that bad in Oakland, Palmer’s record as starter was just 8-16 and in 2013, he was gone to Arizona. Kirkpatrick has been a fixture in Cincinnati’s defensive backfield since 2012, starting 48 of his 80 games and registering 232 tackles, 10 interceptions (two for TDs) and 55 pass deflections. Bernard has been great as a dual threat back-up running back in five seasons, running for 2,900 yards and 16 TDs, along with 2,060 receiving yards and another eight touchdowns.

(AP Photo/Marcio Jose Sanchez)

16. New Orleans Saints Give Away RB Darren Sproles For Fifth Round Selection – 2014

Drew Brees once said, “you only see a Darren Sproles type of player come around once in your career.” Pretty high praise coming from a surefire Hall of Fame quarterback. It made little sense, then, when the New Orleans Saints traded the highly versatile running back/kick returner to Philadelphia for a 2014 fifth round draft pick. The “Lightning Bug”, who has been a three-time Pro Bowler and won a championship with the Eagles, piled up 1,067 rushing and 1,981 receiving yards, along with 21 touchdowns in three years with New Orleans leading up to the deal. In fact, in 2011 he led the NFL in all-purpose yards with 2,696 yards. Since going to Philly, Sproles has kept up his admirable play, recording 1,145 rushing yards in 49 games (9 starts), as well as 1,275 receiving yards and 14 touchdowns. He also led the NFL in punt return yards and punt return touchdowns two years in a row (2014 and 2015). The player the Saints got in the draft, LB Ronald Powell, played in 14 games during the 2014 season (no starts) and had two tackles. He was released and hasn’t caught on anywhere else.

(AP Photo/Bill Feig)

15. Kansas City Trades TE Tony Gonzalez to Atlanta – 2009

Round about 2019, Tony Gonzalez should be a first ballot Hall of Famer. The 14-time Pro Bowler and six-time First Team All-Pro caught 1,325 passes for 15,127 yards and 111 touchdowns in 17 seasons. As durable as they came — he missed just one game — one of the game’s greatest tight ends ever broke the 1,000 yard barrier four times and led the league in receptions with 102 in 2004. For some odd reason, the Kansas City Chiefs thought that after his fourth 1,000 yards-plus campaign in 2008 that trading him (which he had broached to the team because he was it, offensively) would be a good idea. So, in 2009, the Chiefs sent him to Atlanta for a second round draft pick, in 2010. Yes, a second-round draft pick for the career leader among tight ends in TD receptions. Gonzalez would go on to play five more seasons with the Falcons, amassing 4,187 yards on 409 receptions and scoring 35 more TDs. That pick K.C. got? He turned out to be CB Javier Arenas (50th overall), who started 12 of 47 games in Kansas City and is now looking to play in the CFL.

(AP Photo/Dave Martin, File)

14. Miami Trades Draft Pick For QB Daunte Culpepper – 2006

In the early part of the last decade, the Miami Dolphins weren’t a great football team and they had a quarterback crisis, specifically they were being helmed by Gus Frerotte, who was no one’s choice as a starter. The Fish were coming off a non-playoff 9-7 season and were trying to decide whether to go after Minnesota’s Culpepper, or San Diego’s Drew Brees. As Brees was coming off shoulder surgery, the decision to pursue Culpepper, who was rehabbing a knee but was closer to recovery, was academic. Thus, the Dolphins thought they got a great deal by sending a 2006 second round draft pick to Minny to obtain the two-time First Team All-Pro and 2004 NFL passing yards leader. Culpepper was awful in just four games with Miami, posting a 1-3 record and throwing for 929 yards, two touchdowns and three interceptions. Minnesota’s second round pick turned into center Ryan Cook, who played 70 games with the Vikes, mostly as a guard, starting 40.


13. Indianapolis Colts Trade First Round Pick To Cleveland For RB Trent Richardson – 2013

The Cleveland Browns recent history is a sad milieu of bad trades, bad drafts and worse play on the field. In a roundabout way, the Browns won and lost the trade that sent RB Trent Richardson to the Indianapolis Colts in 2013. Richardson, who broke Jim Brown’s record for TDs by a rookie running back in 2012 (11), started just two games for the Browns in 2013 and was traded to the Indianapolis Colts, who were looking for a replacement for injured starter Vick Ballard. Richardson would struggle and be out of football following a disappointing 29 games in a Colts uniform. Following the trade requires a bit of patience. The Browns “won” in that they were able to unload Richardson to re-stock the cupboard and have two 2014 first rounders. After selecting CB Justin Gilbert eighth overall, they traded the pick they acquire from Indy, no. 26, to Philadelphia for their pick, 22nd overall. Here is where they “lost.” They used the 22nd pick to take massive bust, QB Johnny Manziel.

(AP Photo/Darron Cummings)

12. Oakland Trades Randy Moss To New England – 2007

Like the Cleveland Browns, the Oakland Raiders were a hot mess last decade. They were coming off yet another cruddy season in 2006, going 2-14 under the unfortunate Art Shell. Wide receiver Randy Moss, who led the NFL three times in touchdown receptions and had posted seven seasons of 1,000 or more yards up until that season, was coming off a statistically poor year. He caught just 42 passes in 13 games for 553 yards and three TDs in 2006, making him expendable in the team’s eyes. The Raiders felt all they needed in return for shipping him to New England was a fourth round draft pick in 2007. Moss went on to have yet another fantastic year with the Patriot, catching a personal best 23 TDs (tops in the loop) on 98 catches and another personal best 1,493 yards. The Pats also went undefeated that season and won another AFC championship. The fourth round pick that Oakland recouped was Cincinnati Bearcats CB John Bowie, who played five games in a Raiders uniform and made two tackles.

(AP Photo/David Duprey, File)

11. Houston Oilers Send Steve Largent To Seattle For An Eighth Round Pick

One of the worst all-time trades looks worse only in hindsight. In 1976, the Houston Oilers took a flyer on Tulsa wide receiver Steve Largent in the fourth round of the draft, picking him 117th overall. He was an all-America and caught 51 passes for 1,000 yards and 14 TDs for the Golden Hurricane in 1975. He didn’t perform well in four pre-season games with the Oilers, who were going to cut him, but instead dealt him to the expansion Seattle Seahawks for an eighth round selection in the 1977 draft. As it turned out, that late round selection for Largent was highway robbery. The sure-handed, if not overly speedy Largent would play 14 great seasons in Seattle, eight times surpassing 1,000 yards in receiving and catching 100 TD passes. He was a first ballot Hall of Famer in 1995.

Source: Seattle Seahawks

10. St. Louis Rams Deal Jerome Bettis To Pittsburgh For Two Draft Picks – 1996

For most of the 90s, the Rams franchise was an also ran in the NFC, posting nine straight losing seasons from 1990 to 1998. Bettis, who the Rams picked 10th overall out of Notre Dame, quickly became their best offensive threat, rushing for 2,454 yards and 10 TDs his first two seasons. The Rams selected future bust Lawrence Phillips in 1996 and for some reason wanted to move Bettis to fullback to make room for the collegiate star. Bettis’ production fell off to just 637 yards rushing and three scores in 1995, prompting the staff to want to make that move. Figuring that Phillips was the answer, they moved Bettis and a 1996 third rounder to the Steelers for a second (1996) and fourth round pick in the 1997 draft (not amounting to much). The “Bus” would become one of Pittsburgh’s all-time great runners, scampering for 10,571 yards and 78 touchdowns in 10 seasons. He won a Super Bowl (XL) with them and was a four-time Pro Bowler. As we all know, his successor Phillips played just 25 games with St. Louis and was out of football by 1999.

(AP Photo/Tony Tribble)

9. Dallas Trades Up With Seattle To Pick Tony Dorsett – 1977

How good would Tony Dorsett and Steve Largent have looked in Seahawks uniforms together? A year after robbing Houston to get future star wideout Largent, the Seahawks sent their first round pick in the ’77 draft (second overall) to Dallas for the Cowboys first rounder (14th overall) and three second round picks. On the face of it, not a bad deal, but its effects would have lasting implications. Big D took Pittsburgh’s Heisman Trophy winner Dorsett, while the Seahawks took Tulsa guard Steve August, then three inconsequential players in the second. Dorsett, despite his small size, would become one of the game’s premier rushers, eight times running for over 1,000 yards and ending his 12-year career (11 with Dallas, one with Denver) with a Super Bowl ring and 12,739 yards rushing, which was then second only to Walter Payton on the all-time list.

(AP Photo/File)

8. Washington Redskins Obtain Clinton Portis From Denver – 2004

Once mighty, the Washington Redskins were just a run-of-the-mill football club in the early part of the last decade. After winning a Super Bowl title in 1992 (XXVI), their second in five seasons, the Skins fell on hard times, recording just four winning seasons between 1992 and 2003. After a 5-11 finish in ’03, Washington went looking for a game-changing offensive player to snap them out of the doldrums. Lo and behold, the Denver Broncos dangled premier RB Clinton Portis, who was coming off a 2003 season that saw him rush for over 1,500 yards (1,591) for the second straight season. Between 2002 and 2003, he also scored 29 touchdowns and led the NFL in yards per carry in 2003 at 5.5.  Portis, despite a few good seasons with the Redskins, battled injuries and missed 28 games of a possible 112 and was released after an injury riddled 2010 campaign. Going the other way was six-time First Team All-Pro cornerback Champ Bailey, who would anchor the Broncos defence for nine good seasons, leading the NFL in interceptions with 10 in 2006. The Broncos also got Washington’s second round pick in 2004, who turned out to be RB Tatum Bell (2,591 yards rushing, 15 TD in 49 games).

(AP Photo/Ross D. Franklin, File)

7. Miami Sends Wes Welker To New England – 2007

The Patriots have been pretty deft over the years, stealing premier wide receivers for next to nothing in return. Besides the heist of Randy Moss from Oakland in 2007, they also plucked Wes Welker from the Miami Dolphins the same year. The cost? Just a second and seventh round pick in the ’07 draft. Now, in Miami’s defence, Welker was no Randy Moss. He never started his first year with the team (2004) and caught all of 96 passes for 1,121 yards and one TD in the next two seasons. The Patriots caught lightning in a bottle with the diminutive Welker, as he fluorished under Bill Belichick, catching 672 passes in the next six seasons (three times leading the league in receptions) for 7,459 yards and 37 touchdowns. He was also a five-time Pro Bowl selection and two-time First Team all-pro. The draft picks the Dolphins received in return were second round center Samson Satele (three seasons in Miami) and seventh rounder DE Abraham Wright (never played).

(AP Photo/Stephan Savoia)

6. Washington Trades Up With St. Louis To Draft Robert Griffin III – 2012

Trading up in any particular NFL draft is old hat. Some trades work out, others, not so much. In 2012, the Washington Redskins were coming off a horrid 5-11 season in 2011, one where career back-up Rex Grossman was the starting QB. The Skins had their sights set on Robert Griffin III at no. 2 in the draft, and thought it good business to deal their first round picks in 2012 (6th overall), 2013 (22nd) and 2014 (no. 2), as well as a 2012 second rounder 939th overall). The swap looked great in 2012, as RGIII passed for 3,200 yards and 20 TDs (against just five interceptions). He had another decent year in 2013, but injuries have plagued him since, as he’s played just 14 games between Washington and Cleveland, missing the 2015 season entirely. The Rams total haul of four picks turned into seven total through further trades, including DT Michael Brockers (14th, 2012), CB Janoris Jenkins (39th 2012) LB Alec Ogletree (30th 2013) and OT Greg Robinson (2nd 2014).

(AP Photo/Patrick Semansky)

5. Dallas Swaps Three Draft Picks With Detroit For Roy Williams – 2008

Dallas has been equally astute with trades (see Tony Dorsett, 1977) as they have been knuckle-headed, as in the deal for malcontent Texas-born wide receiver Roy Williams in 2008. The Lions were in the midst of what would be a 0-16 season in 2008 and University of Texas product Williams was champing at the bit to get out. After posting a 1,310-yard season in 2006, Williams stats declined as the Lions played some horrid football overall. The Lions had a young Calvin “Megatron” Johnson in the line-up already, making Williams expendable. So, five games into that historic 0-16 campaign, Detroit gave Williams his wish, packaging him up for first (20th, TE Brandon Pettigrew), third (82nd Derrick Williams) and sixth (192nd Aaron Brown) picks in the 2009 draft. Williams never hit his stride from the get go in Dallas, including just 198 yards receiving in 10 games during the remainder of the 2008 season. Over the next two in Big D (18 games started out of 30), he caught 75 passes for 1,126 yards and 12 TDs.

(AP Photo/Tony Gutierrez)

4. Washington Obtains Donovan McNabb From Philadelphia – 2010

From what we can see here, the Washington Redskins are the Kings of the dubious deal. Now, they couldn’t be faulted, at least at first blush, for sending a second round pick in the 2010 draft and a conditional third-fourth rounder in 2011 to get QB Donovan McNabb. The Skins were 4-12 in 2009 and used three different pivots, principally the so-so Jason Campbell. McNabb was a six-time Pro Bowler and 2004 NFC offensive player of the year that the Redskins had seen all too much of, playing in the same division. McNabb started out well enough during the 2010 season, but his play fell off gradually to the point he finished the season on the bench for the final three games. In his 13 total starts, he passed for 3,377 yards, 14 TDs and 15 INTs (the first time his differential was negative). Of the selections going Philadelphia’s way, further wheeling and dealing netted DB Nate Allen, LB Casey Matthews, QB Nick Foles and LB DeMeco Ryans.

(AP Photo/Nick Wass)

3. New Orleans Sends Jimmy Graham To Seattle For Max Unger And First Rounder – 2015

The tale of this trade is still playing out. On the face of it, Seattle wins right now, depending how the career arcs of the principles go. Why the Saints, who have a premier QB in Drew Brees, sent dependable TE Graham to Seattle is a head-scratcher. In five seasons and 78 games (50 starts) with NOLA, Graham caught 386 passes for 4,572 yards and 51 touchdowns, including a league leading 16 in 2013, when he went to his second of four Pro Bowls so far. In March 2015, New Orleans sent Graham the Seahawks way in what could also be perceived as a cost-cutting move, as Graham was the highest paid TE in the league after signing a four-year, $40 million deal in 2014. He had an injury shortened 2015 campaign, but bounced back in 2016 to garner his fourth Pro Bowl nomination on the strength of a 923-yard, six TD season. As for Unger, he hasn’t made it back to Pro Bowl status with the Saints and will start the 2017 season on the PUP list with a foot injury. The first rounder (31st overall, 2015), LB Stephone Anthony, was stellar in his first season, but injuries have hampered his effectiveness since.

(AP Photo/Elaine Thompson)

2. New England Trades Down And Misses Chance On Jerry Rice – 1985

Some trades are so pivotal, they have to be called an all-time heist. The New England Patriots, pre-Bill Belichick, can be forgiven for not knowing how good their first round (16th overall) pick in the 1985 draft was going to be, whoever it was. Well, as it turns out, the Pats were convinced by the 49ers to trade that 16th pick (not a bad idea at the time) for the 27th pick, the 56th pick and 84th pick. It wasn’t common practice then, but Rice was coveted highly by 49ers legendary coach Bill Walsh to use in his West Coast offensive scheme. It was Walsh’s crown jewel, as it turns out, with Rice going on to become the greatest wide receiver of all time. He won three Super Bowls and holds the record for most career receptions (1,549), receiving yards (22,895) and receiving TDs (197). None of who New England got in return ever panned out. At least they were able to wash a little of the smell away from that deal with the steals of Wes Welker and Randy Moss years later.

(AP Photo/Bill Haber/FIle)

1. Tampa Bay Buccaneers Ship Steve Young To San Francisco – 1987

Just two seasons after pulling off a huge draft swindle with New England to get WR Jerry Rice, the already rich 49ers pulled off another sweet deal with Tampa Bay in 1987. Steve Young, who began his career in the USFL, was actually picked in the 1984 supplemental draft by Tampa Bay. He played just a season and a bit in the upstart league before financial problems saw him leave for Tampa. Yet, the formal collegiate standout could do no better than a 3-16 record between 1985 and 1986 with the Bucs, prompting the team to draft Vinny Testaverde first overall in the 1987 draft, signalling the end of Young’s tenure there. He was dealt to San Fran, where Joe Montana was still king, for a second round pick in 1987 (LB Winston Moss) and fourth rounder (WR Bruce Hill). After apprenticing under Montana for most of the next four seasons, Young got the starting job in 1991 and never looked back. He, as well as Jerry Rice, would win three Super Bowls, as well as two MVP trophies and a Super Bowl MVP. Young ended his career with the fifth highest passer rating (96.8) and the holder of several post-season records, including most TD passes in one Super Bowl (six) and most rushing yards by a QB, post-season career (594).

(AP Photo/David Longstreath, File)