Living With Regret: Every NFL Team's Most Embarrassing Trade

Sustained success in the NFL isn't built only on the draft as some may lead you to believe, it's also accomplished through well executed trades for draft picks, veteran pieces, or young unproven talent. Elite GMs and personnel executives like Bill Belichick, Bill Polian, and Mickey Loomis as well as others have built their teams in this way.

We have great examples of trades by the mentioned GM's and others that proved to be linchpin pieces for the teams involved. Joe Montana to the Chiefs, Randy Moss in New England, the Elway draft day fiasco. Those were arguably three of the most positive impact trades in NFL history, but what about ones that didn’t end in a happy-ending?

Each team has had a blunder on the trade market at one time or another but what were the biggest regrets by each franchise? Let’s take a look.

32 Arizona Cardinals: Trading FOR Kevin Kolb

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Coming off a disappointing 2010 season where they finished 5-11, the Cardinals had to make a move for the future, and they did.

Arizona sent over cornerback Dominique Rodgers and a second round draft choice in exchange for Kolb. If the price they paid wasn’t bad enough, they handed out a hefty extension of $64mil over 5 years.

But, wait, surely you’re thinking that since the Cards’ backed up the brinks truck that at the bare minimum Kevin Kolb would be ‘adequate’... WRONG. Kolb would finish with his first season starting with a humble 1,955 yards, 9 TDs and 8 INTs, whilst completing 57.7% of those passes. Arizona threw in the towel on the deal the following season by benching Kolb for John Skelton. Kolb would go on to start due to injuries in several games during the 2012 campaign but never found his footing and was released prior to the 2013 season.

31 Atlanta Falcons: Trading AWAY Brett Favre

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Everyone and their mother knows hall of fame quarterback Brett Favre, and rightfully so, he is an all time Green Bay Packer and NFL great. But before Brett laced up at Lambeau he was stationed in the deep south playing for the Dirty Birds.

The Falcons’ head coach at the time, Jerry Glanville didn’t want any part of drafting, playing, or coaching Favre and thus had him shipped to the frozen tundra and cheese capital of the known world… Green Bay, Wisconsin. As they say, the rest is history. Favre went on to make 11 pro bowl’s, win Super Bowl XXXI, and finish hang up his cleats as a hall of fame quarterback.

Had Coach Glanville put his differences aside, and Atlanta not caved to his request, would Favre turned into the all-timer that he’s known as today? Who knows. But what we do know, is if Atlanta could do it all over again, you can bet the farm they would.

30 Baltimore Ravens: Trading FOR Willis McGahee

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Oh, what could’ve been. Willis McGahee had what looked to have -- at the very least -- Pro Bowl potential year in and out. But injuries never allowed him to develop into that super star like talent that most thought he would.

The Ravens took a chance and hopped on the McGahee hype train by trading a pair of third round picks and a seventh round pick to the Buffalo Bills prior to the 2007 season for Willis. Baltimore then signed him to a fat 7 year, $40mil+ contract. Despite rushing for more than 1,200 yards, new head man John Harbaugh put McGahee in the doghouse and focused on Ray Rice as the Ravens’ primary playmaker. Willis McGahee never saw much action again as he was relegated to bench warming duty in his final three seasons in Baltimore.

He finally retired in 2013 after stints with the Broncos and Browns making many wonder, as we said at the outset, what could’ve been.

29 Buffalo Bills: Trading AWAY Sammy Watkins

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Just because the Bills haven’t made the playoffs in kids born after the year 2000’s life, don’t let that distract you from the fact that they actually don’t make many bad trades. But trading up for Sammy Watkins in the 2014 draft was one of them.

Watkins flashed generational talent while shining at Clemson and that in turn motivated the Bills to trade up to land his services. Buffalo parted ways their current 1st rounder, the following years’ 1st and 4th round choice to land Sammy. Yikes.

The first two years of Watkins’ career showed promise, but were also filled with nagging injuries and dropped passes at an uncomfortable rate. After a huge drop off in the 2016 season the Bills parted ways with Watkins and are still in search of a true number one receiving option.

Needless to say, if they could do it over again and not make that trade, they probably would.

28 Carolina Panthers: Trading FOR Armanti Edwards

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Like Buffalo, the Panthers worst trade was a draft day move. Carolina decided to make a move up in the 3rd round of the 2010 NFL Draft and select Armanti Edwards.

During his tenure, Edwards played all over for Carolina as the Panthers looked to get him the ball in space, but alas, it didn’t come to fruition. Armanti was plagued with injuries throughout his career and is now playing in Canada for the Toronto Argonauts.

The Panthers are still looking for a DeLorean that can hit 66 mph and send them back to 2010 where instead of selecting Edwards, they would have selected all-pro linebacker NaVorro Bowman, elite tight end Jimmy Graham, or secondary superstar Kam Chancellor instead

27 Chicago Bears: Trading AWAY Greg Olsen

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For whatever reason the Bears decided to trade away one of their few reliable offensive weapons at the time, Greg Olsen. Olsen had been a steady contributor with Chicago and had developed a great rapport with quarterback Jay Cutler in the 09’ season, but sure, trade him away.

Olsen proved to the Bears that cutting ties with him was the worst possible move for them, and has went on to post career highs while becoming not only a fan favorite, but a team favorite too. Cam Newton thanks you, Chicago, for giving him a reliable weapon in the passing game.

26 Cincinnati Bengals: NOT Trading AWAY AJ McCarron

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On the trade deadline in the 2017 season, by all accounts the Browns and Bengals had pulled off a last second deal that would send AJ to Cleveland. Although the Browns are mostly at fault for this debacle (not answering the Cincinnati email), I’m placing a lot of blame on the Bengals front office.

You’re telling me that in 2017, when we have social media til’ kingdom come, messaging apps, facetime, skype, calls, and texts, that not one person in Cincinnati was not in a position to contact Cleveland at all? That the only way of contact was by email, and that’s why the trade wasn’t finalized? Sorry, I’m not buying it. Cincinnati, you dropped the ball and missed out on a great haul for your backup QB, and I know you want this one back.

25 Cleveland Browns: Trading FOR Johnny Manziel


Johnny Football: what to say, what to say. Starring for the Texas A&M Aggies, Manziel quickly tantalized the college football world with otherworldly performances against Alabama, Auburn, Arkansas, and several others.

When you hear his name, what you probably think of is his innate ability to get out of trouble with his eyes still downfield, and execute the play. That natural excitability trait coupled with his bazooka-like arm made him a favorite among NFL general managers, and as usual, Cleveland was one of them. The Browns pulled the trigger on a deal that would place them at the 22nd overall pick instead of 26th, and in prime position to draft Manziel.

As we all are aware, it was a colossal failure. Manziel did have a few good moments during his first year of live game action, but outside of that, not much was done. Johnny Football went on to finish his Browns -- and NFL career -- with a total of 7tds, 7ints, and sub par passing rating overall, Johnny Manziel might go down as one of the biggest regrets of all time. Especially so, when you consider that the Browns passed on Derek Carr, Teddy Bridgewater, and Blake Bortles.

24 Dallas Cowboys: Trading FOR Roy Williams

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Jerry Jones doesn’t make many bad deals but when does… man oh man, does he ever. Following the Detroit Lions 0-16 season Jones thought he might capitalize on the demise going on in The D but sending a first, third, and sixth-round draft choice for the return of former Lions receiver Roy Williams and a seventh rounder wasn’t the best decision Jones has ever made.

The picks traded were bad enough as it was, inking Williams to a 5 year, $45mil deal with $20mil -- that’s right, $20 MILLION guaranteed -- made this whole situation a nightmare for the Cowboys.

Williams never lit the world on fire while in Dallas and after the Cowboys drafted -- now star receiver -- Dez Bryant in 2010, the writing was on the wall and Roy was subsequently released in 2011.

23 Denver Broncos: Trading AWAY Jay Cutler

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Once upon a time, Josh McDaniels was the head coach, -- and made personnel decisions for -- the Denver Broncos. He was widely renowned as the best, young coach in the game and that’s why Denver gave him the keys to the franchise. Bad choice.

Before McDaniels’ arrival, Cutler had just thrown for 4,526 yards (which is still Cutler’s career high). So McDaniels groomed him to become NFL elite, right? Well, obviously not. Cutler was traded to Chicago and then the wheels came off in Denver.

I’m sure they’d love to redo the Josh McDaniels hire in the first place, but keeping Cutler around might not have been a bad idea as they’re still searching for a QB in the post Manning era.

22 Detroit Lions: Trading FOR Mike Thomas

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Mike Thomas lit up the scoreboard and the Pac-12 conference while he attended Arizona back in his college days. Coming out of college, Thomas boasted a 4.30 40yd dash and was drafted by the Jaguars.

He could never put it together while in Jacksonville, so he became available via trade, and Detroit pounced by offering a 4th round draft pick for Thomas.

It turned out that Thomas’ limited success in Jacksonville was nothing more than a flash in the pan and couldn’t be sustained in Detroit. The Lions cut him a year after trading for him and probably want that draft pick back.

21 Green Bay Packers: Trading FOR John Hadl

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Probably too long ago for most readers to remember, but back in 1976 the Packers bet the farm on John Hadl… it didn’t work.

Green Bay was needing to make a move, and boy did they ever. The Packers sent 2 first round draft choices as well as 2 second rounders over the course of two years. That disastrous move set the Packers back several years as Hadl never returned to his all-pro form. If they didn’t make the trade for Hadl, there wouldn’t have been any down era in the post Lombardi days.

20 Houston Texans: Trading AWAY Brock Osweiler

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Brock Osweiler has turned out to be nothing more than a lot of thunder, and no lightning as he never lived up to anything resembling the expectations put upon him when he signed with Houston a few short seasons ago.

What made matters worse is the fact that instead of just eating the remaining cash on Brock’s contract, the Texans sent him to Cleveland along with their own second, fourth, and sixth round picks over two years.

Now with an injured Deshaun Watson, no Osweiler, and less draft picks, it makes this entire situation even more regrettable

19 Indianapolis Colts: Trading FOR Jeff George

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In search of a franchise QB, the Colts made a deal with Atlanta for the #1 overall pick in the 1990 NFL Draft and used the pick on Jeff George, a homegrown Indiana product. It didn’t work out.

George spent four uninspiring and uneventful seasons in Indy finishing with a 14-35 record as a starter, 46 TDs to 41 INTs and was traded in 1994 to Atlanta. Although the Irsay’s must regret this move, hope was not lost for the Colts as Jim Harbaugh rode into town a couple years later and delivered for the city. A move as bad as this one was could’ve been much worse had they not eventually found their guy.

18 Jacksonville Jaguars: Trading FOR Branden Albert

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The Jaguars needed help on the offensive line especially at both tackle positions. That’s why they made the move to acquire Branden Albert who played left tackle for the majority of his career. But being the age that he was, it was still a risk.

What looked like a solid move at the time to add depth at the very least backfired on Jacksonville when he announced his retirement prior to training camp. Branden has not returned to the NFL since his last stint in Jacksonville, and doesn't plan on doing so.

If the Jags could do it over again, they would’ve looked at other options.

17 Kansas City Chiefs: Trading FOR A.J. Jenkins

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In a move where the Chiefs and 49ers swapped disappointing draft picks with A.J. Jenkins heading to Kansas City and Jon Baldwin going to San Francisco, it looked like it all might work out for the Chiefs at least. But they wouldn’t be on our list if it did.

Coming out of college AJ was regarded as a starting caliber prospect with a lot of upside, which never came to fruition.

Jenkins (who is now out of the league) only stayed in KC for one year and was released at the end of the 2013-14 season.

16 Los Angeles Chargers: Jacob Hester

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At the collegiate level, Jacob Hester was a star halfback at Louisiana State, rushing for 1,780 yards and 20 touchdowns. That's why the Bolts made a move up to land his services by unloading a 2nd and 5th round pick.

Hester was a productive player for the Chargers, but was not worth the heavy price tag they paid. Jacob was used primarily as a fullback and short-yardage back with the team, which is why the price tag was too high. Hester -- as mentioned earlier -- was a very productive player but in his limited roll. He became an elite level blocker in the backfield, but ran for only 319 yards in four years with the Chargers.

Due to the lack of fit, role, and production, Los Angeles (then located in San Diego) released him in 2012.

15 Los Angeles Rams: Trading AWAY Greg Robinson

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A star left tackle coming out of Auburn University (AL), Robinson was a sure fire bet to start, and star, on the Rams suspect o-line. But it never happened that way.

Greg Robinson has gone down -- to date -- as one of the biggest offensive line busts in recent memory but still, as a #2 overall pick,  had a lot of potential which makes trading him away for a measly 6th round pick underwhelming to say the least.

In hindsight it might have been best to hold onto Robinson and hope he develops, or have waited out a better return. The Lions cut him during the 2017-18 season.

14 Miami Dolphins: Trading AWAY Vontae Davis

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Vontae Davis was on his way to stardom when Miami decided to trade him away to Indianapolis in 2012.

That trade sent Davis to the Colts just before the start of the season for a 2nd round pick in the 2013 draft. The Dolphins used that pick to draft his replacement Jamar Taylor. More bad news for Miami is that the would be replacement, Taylor, has not panned out to date and has been more of a negative addition than positive. Meanwhile, Davis is still playing at a very consistent level in Indianapolis and though reaching the end of his career, is still an elite defensive back.

13 Minnesota Vikings: Trading FOR Herschel Walker

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There’s an ESPN 30 for 30 movie on this trade for a reason. The Vikings -- thinking they got the best part of the deal -- were overjoyed to land superstar running back Herschel Walker. But head coach Jimmy Johnson and owner Jerry Jones had something in mind, when they fleeced the Vikings.

Johnson and Jones would turn that one trade into the re-establishment of the Cowboys dominance over the league, and would send the Vikings into a long and difficult road to recovery.

Put these teams in this position again and the Cowboys pull the trigger 100 times out of 100. The Vikings on the other hand, they’d hang up the phone the second they heard who was calling.

12 New England Patriots: Trading FOR Duane Starks

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The Patriots are usually outstanding at finding diamonds in the rough or making a savvy move for a veteran player, but this time it didn’t work out.

The Patriots traded a third and fifth round pick to acquire Starks and a fifth rounder. Starks provided a nice veteran presence, but not much else. He was very ineffective on the field and his playing time was limited, mostly due to a shoulder injury.

Bill Belichick is leaned back in his La-Z-Boy with a cold one popped, reading this and laughing because he knows his track record.

11 New Orleans Saints: Trading AWAY Willie Roaf

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Starting as an offensive lineman in New Orleans, Roaf was playing his way into the hall of fame with each snap that he took. He was also getting one step closer to the door with every locker room dispute that occurred.

At some point, the locker room disputes and contempt overall for Roaf became too much to handle as the Saints made the decision to deal the future hall of famer for a conditional draft pick. That draft pick would be used to draft a starting safety, but was not the same impact as Roaf. Instead of working through said issues, they let him go. They let a hall of famer go.

Willie would go on to play in four more pro bowls for Kansas City, and now today, has his name in Canton, OH, in the hall of fame.

10 New York Giants: Trading FOR Craig Morton

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During the 74’ season, the Giants were so desperate for a QB that they a traded a first-round draft choice to the Dallas Cowboys for Craig Morton. The Giants couldn’t get it rolling with Morton as their starter for two and a half years, posting a 7-25 record with Craig as their starting quarterback.

Of course, just by coincidence, Dallas used that New York 1st rounder to select Randy White, who would end up as a nine-time pro bowler and seven-time all-pro who also became a hall of famer.

9 New York Jets: Trading FOR Tim Tebow


Tim Tebow didn’t do much to win over the hearts of the owners and fans during his tenure in New York, and stayed for not much more than a cup of coffee. Why an all time great college quarterback with a good arm never panned out in the pros is a mystery, but like the Broncos before, and the Patriots after, the Jets fell victim to the Tebow love.

Like a lot of the other teams on our list, when desperate for a quarterback, you tend to overlook red flags, and other flaws. Welcome to that list, “J-E-T-S JETS JETS JETS!”

8 Oakland Raiders: Trading FOR DeAngelo Hall

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After four years with the Falcons where he established himself as an upper echelon defender in the NFL, Atlanta traded DeAngelo Hall to Oakland where the Raiders promptly signed him to a generous deal worth $70 million over seven years, with $24.5 million guaranteed.

In his first game as a Raider it was apparent even then that he wasn’t a fit for the Raiders' man-to-man defensive scheme. He was cut eight games into the season, adding to the long list of terrible moves the Oakland Raiders have made.

7 Philadelphia Eagles: Trading AWAY LeSean McCoy

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LeSean "Shady" McCoy has been one of the best and most consistent running backs in the NFL each and every year during his time in the league. He has a knack for finding, and hitting the hole with a burst of speed that's been unmatched during his time in the NFL. With his a diverse skills of not only running, but with receiving ability out wide, in the slot, or in the backfield. That’s why trading him away from a system that seemed to fit him to a tee was questionable to say the least.

McCoy has continued that consistency despite being traded away to Buffalo in a move that Philly used to create cap space. He has gone on to post great numbers throughout his tenure in Buffalo and has made Eagles fans wonder why they ever let him go.

6 Pittsburgh Steelers: Trading FOR Josh Scobee

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It’s not very often that a kicker is traded, and when he is, it usually works out. It didn’t in the case of Josh Scobee and the Steelers.

Needing an immediate fix in the kicking game, Pittsburgh struck a deal with the Jags and banked their success on Scobee by thrusting him into a starting role as soon as he rolled into town.

Scobee rewarded Pittsburgh's leap of faith by missing huge kicks against the Patriots and Ravens which led to the Steelers losing both games. The Steelers ended up cutting Josh before the 5th week of the season, and would test out a couple other kickers before settling on one. As they say, hindsight is 20/20, and if Pittsburgh knew what they were getting into, they would've hit up the free agent market before swinging for the fences with this move.

5 San Francisco 49ers: Trading FOR Kentwan Balmer

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Coming off a disappointing 2007 season, the 49ers were a struggling franchise that looked desperately to get back to their roots by establishing an identity on the defensive side of the ball.

Because of that need, they overlooked available offensive talent in the draft, and made a move up in the daft to the 29th overall spot to select defensive lineman Kentwan Balmer out of North Carolina.

Despite the high expectations of the 49ers, Kentwan didn’t live up to the hype. His stay in the bay area was nothing more than a cup of coffee as he faded out of the defensive rotation and then found himself out of the league by 2012. 

Had the 49ers known that they would soon find success by making three straight conference championship games, they would've looked to add needed depth, or maybe offensive talent instead of making this reach.

4 Seattle Seahawks: Trading FOR Brian Bosworth

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A national sports icon, a college football star, and undeniable eccentric personality, Brian "The Boz" Bosworth was a polarizing figure as well as stud football player.

Like the 49ers, the Seahawks swung for the fences on the defensive side of the ball in the draft, and traded up to select Brian Bosworth out of Oklahoma in the 1st round.

While Bosworth was an amazing collegiate talent, much like Tim Tebow who we mentioned earlier, he didn’t find his niche in the league and flamed out after 2 short, and unforgettable seasons in Seattle. Now a focus of a recently released ESPN 30 for 30 documentary, the trade the Seahawks made was a regrettable one.

3 Tampa Bay Buccaneers: Trading FOR Darrelle Revis

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Darrelle Revis established himself as the best cornerback, hands down, in the NFL throughout his career and earned the title and nickname, “Revis Island”. He could go man-to-man with the best of them and continue to hold his own each and every game, but when you’re on a floundering team like the Bucs’ that only helps so much.

Tampa Bay forked over a about $16mil in cap space, a 1st and a 4th round pick. The Patriots said thank you, Tampa Bay. You not only set yourself back, but you gave New England yet another elite piece to work with for that short time.

2 Tennessee Titans: Trading FOR Marcus Mariota

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Heisman winning quarterback Marcus Mariota has been a tantalizing player for not just his collegiate career but for the start of his NFL one has well. That is why what I'm about to say is a hot take -- maybe even a burning one at that-- , folks, and I’m well aware of that. Marcus has, at times, shown that he’s a pretty good quarterback. But this season, the 2017-18 season, he isn’t living up to expectations and has shown an uneasy amount of regression. Which may be the start of a downhill slide to the former #2 overall pick's career.

This is a wait and see situation, but with the amount Tennessee gave up to snag Mariota at the aforementioned #2 pick, this has the potential to become a regrettable trade, that’s for sure.

1 Washington Redskins: Trading FOR Donovan McNabb

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Washington took a chance on a once generational talent, and it backfired. Donovan McNabb at one time was one of the most -- if not the most -- electrifying talents in the game, and that’s why the Redskins gave up a 2nd round pick for him.

Bad news for Washington, though, McNabb was over the hill before he even came into town and was benched for the final 3 games of the season, and for the first time in his career finished the season with more interceptions than touchdowns.

Ask Donovan or (owner) Dan Snyder and the Redskins, they’ll both tell you they want a redo at this.

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