Every NFL Team's Most Regretful Free Agent Signing

While writing this article, I accidentally spelled signings wrong from typing too fast and went to have my computer automatically correct it. The word it suggested was misgivings, which is an appropriate word for the topic of today's article: bad, bad NFL signings.

Not every free agent signing is going to work out for teams - the New Orleans Saints and Adrian Peterson are a prime example from this season alone - but why not rub it in on teams and their fans by looking at the signings each of the league's 32 teams regret most.

Yes, there are some ground rules here! For starters, we're looking at players who signed their free agent deals from 2000 to now, although there is one player from the 90s who is going to get mentioned and you'll see why. Players who re-signed only to do nothing or make the team regret re-signing them (i.e. Brett Favre in 2010 with the Minnesota Vikings) are ineligible, as are undrafted free agents. Also, players like DeAngelo Hall who were traded to a team and immediately signed an extension with them are ineligible as well; these are all purely free agents, not players under contract who worked out a new contract.

If you're ready to relive some of the worst contracts in recent NFL history and try to block out memories you've likely repressed over the years, let's get to work.

32 Arizona Cardinals: Derek Anderson, QB (2010)

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One of the very few players on this list that is still active in the NFL today, current Carolina Panthers quarterback Derek Anderson "wins" what wasn't a very crowded contest. Many will make a case for Emmitt Smith, but was that regretful so much as it was a move that didn't panned out? At least with Anderson, the Cardinals can look back and ask why it was the former Pro Bowl, one-year wonder they went after in free agency rather than pursuing a trade for a Donovan McNabb or a Tavaris Jackson (not that he'd have been much better, but still).

Between abysmal performances and an infamous Monday Night Football meltdown, it's safe to say the Cardinals are glad they've moved away from the Derek Anderson era.

31 Atlanta Falcons: Ray Edwards, DE (2011)

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We discussed Edwards, who most recently fought Keenan "Good Burger" Hickman in November 2016, when looking back at every NFL team's most disappointing move over the past ten years. Will we see other names from that list again here? Perhaps, but Edwards and the five-year deal he signed with the Falcons following the 2010 season were a guarantee. Given how many players on this list never even took the field for their team, Edwards recording 3.5 sacks in 2011 is worth slight praise, but there's not much else to compliment him on.

While Steven Jackson did disappoint at running back, he falls into the Ed Reed-Houston Texans category of it only being regretful because a future Hall of Famer was signed and years of a heavy workload caught up to him. It could be worse, as we'll see with the rest of this list.

30 Baltimore Ravens: Elvis Grbac, QB (2001)

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We're going to spare you an "Elvis has left the building" pun because, honestly, I don't think Baltimore was ever desperate enough to have security escort Grbac out of their practice facility. Hoping Grbac's 1999-2000 showing of combined 7,558 yards, 50 touchdowns, 29 intercptions, and a 59.3 completion percentage weren't a fluke (given the former eighth-rounder had thrown for five interceptions to 12 touchdowns in 1998, it was surely a possibility), the Ravens signed the Michigan alum as their replacement for "competent game manager" Trent Dilfer.

Given Baltimore wanted to make their offense explosive and not rely entirely on their record-breaking defense, I don't think they regret letting Dilfer go or giving Grbac a chance. Instead, it's the five-year, $30 million dollar contract to a quarterback who would be 31 on Opening Day 2001 which may have been a mistake.

29 Buffalo Bills: Derrick Dockery, OT (2007)

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This was a rough, rough move for the Buffalo Bills, one that screamed desperation by returning general manager Marv Levy. After being a solid - not elite, but solid - guard with the Washington Redskins who battled false start issues, Levy and the Bills signed Dockery to a seven-year, $49 million contract in March 2007 with an $18 million signing bonus. Dockery lasted two years before the Bills, in a salary cap move, cut him loose. Woof.

Even better for Dockery, he went back to the Redskins on a five-year, $26.5 million deal, was benched by October 2010, and still collected a fair share of money. Keep in mind, this was the same offseason that saw the Redskins land Albert Haynesworth in free agency, so who cursed the other?

28 Carolina Panthers: Chuck Smith, DE (2000)

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Because the Carolina Panthers are usually the ones on the wrong side of releasing players rather than signing them, this entry is a bit unique. Chuck Smith gets our pick for doing nothing in two games with the Panthers in 2000 after signing a large deal and totaling 53 sacks over his previous six seasons with the Atlanta Falcons, but let's take today to bash all of the moves the Panthers made on the *other* side of the spectrum.

- Releasing Steve Smith for...some reason.

- Removing Josh Norman's franchise tag right before the NFL Draft and allowing the Washington Redskins - a team notoriously bad for free agent signings - to scoop him.

- Basically forcing Jordan Gross to retire and removing Cam Newton's blind side.

Chuck Smith was a regretful signing, but so was letting Dave Gettleman make those types of moves as the Panthers' GM.

27 Chicago Bears: Sam Hurd, WR (2011)

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With Sam Hurd, the Bears aren't regretting this for production or money purposes, but because they didn't do enough of a background check. In November 2013, Hurd was sentenced to 15 years in prison for running a drug operation off the field. In fact, U.S. District Judge Jorge Solis gave Hurd a much shorter sentence than the 27 to 34 years recommended by federal sentencing guidelines.

"I regret not thinking about the consequences," Hurd said during his sentencing."I made some dumb, very bad decisions."

Well, Hurd did say he regrets the situation, so I think that's enough reasoning for him to land on this list. Whether you're looking to sign a free agent receiver or a new janitor, make sure to do those background checks. They. Are. Important.

26 Cincinnati Bengals: Laveranues Coles, WR (2009)

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At first, BenJarvus Green-Ellis seemed like a reasonable option for this list, but the Law Firm simply fell out of favor with the Bengals and was potentially a New England-only product. Had the Bengals paid him something like $30 million to be their running back in 2012, it's a different story, so we're instead going to talk about New York Jets fan favorite Laveranues Coles. Cut by the Jets after the 2008 season's conclusion, Coles signed with the Bengals in hopes of creating a dangerous 1-2 tandem between himself and Chad Ochocinco.

In his lone season with the Bengals, Coles caught 43 passes for 514 yards and five touchdowns, his lowest marks in the first two categories since his rookie season in 2000. Cut by the Bengals before the 2010 campaign, Coles works out as our choice.

25 Cleveland Browns: Jeff Garcia, QB (2004)

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Despite only playing regular season games for five teams, it feels like Jeff Garcia is everywhere. In the hearts of Browns fans, though, Garcia is just another member of the disappointing quarterback club. Signed for to be the answer at a quarterback position that still has no clarity despite a rough 2003 season on and off the field (getting accused of being gay in the NFL is never fun), Garcia went 3-7 in 11 games with a 57.1 completion percentage, ten touchdowns, and nine interceptions. By 2005, Garcia was in Detroit and the Browns were onto their next quarterback.

Bonus points go to the Browns' 1995 signing of wide receiver Andre Rison, when owner Art Modell had to borrow money from various banks. Seriously. When he was still an SI journalist before running the MMQB, Peter King reported in 1995, "Modell had to personally guarantee a $5 million loan to pay Rison's signing bonus." It's only fitting for the Dog Pound that we put WOOF for this entry.

24 Dallas Cowboys: Terrell Owens, WR (2006)

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How could I pick Terrell Owens here when the future Hall of Famer (if he gets his way) actually had some strong years in Dallas? Why didn't I pick kicker Mike Vanderjagt or running back Alfred Morris - right, like I was going to pick the ex-FAU Owl - when Owens did what Owens did best while with the Cowboys? Easy: that right there is exactly why I picked T.O. over those guys.

With all of the off-field drama Owens caused in Dallas - "that's my quarterback!", the suicide drama, fighting with coaches - I don't doubt for a second the Cowboys regretted signing him. At least with Randy Moss in New England, the Patriots were one miracle catch away from a Super Bowl victory. Three years and no playoff wins with Owens and his antics? No game.

23 Denver Broncos: Jarvis Green, DE (2010)

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Why do we not have a picture of Green in a Broncos uniform for this one? Here's a better question: why would the Broncos cut a player they gave a four-year, $11.75 million contract in 2010 - over $3 million of which was guaranteed with signing bonuses and base salary - in training camp? Apparently, Green's play in training camp that year was so bad that it was a no brainer for the Broncos to avoid playing him in their preseason finale against the Minnesota Vikings.

This all begs an important question that I'll revisit several times throughout this list: if you sign a player to a major contract, why wouldn't you even consider bringing him onto the gameday roster if he's healthy? Is it really worth taking that cap hit when you can have him as depth?

22 Detroit Lions: C.C. Brown, S (2010)

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When it comes to free agency, the Detroit Lions have either had successes (Haloti Ngata, Kyle Vanden Bosch) or players who turned out to be "meh" - and there's more than enough players in that spot to name - so our pickings here were fairly short. Is Daunte Culpepper the answer? He'd struggled for some years prior to joining the Lions in 2008, so the answer there is most likely no. We'll go with safety C.C. Brown instead, if only to relive his argument with legendary sports writer Jeff Pearlman.

Writing about the 100 worst players in NFL history, Pearlman said, "As the joke goes, C.C. stands for "Can't Cover." Some players manage to find work no matter how poorly they play. Here's Exhibit A."

Brown's response?

"I mean, I really don't give a s*** about it. It is what it is, man. F*** that list. Whoever said it, you can tell them I said f**** their list and f*** them, too."

Maybe the C.C. stands for Can Curse?

21 Green Bay Packers: Joe Johnson, DE (2002)

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Before telling the story that has been told in Green Bay thousands of times in the past 15 years, I'll let ESPN's Rob Demovsky explain just why this signing went so poorly.

"In 2002, the Packers gave the former Saints defender a six-year, $33 million contract that included a $6.5 million signing bonus. What they got in return was two sacks in 11 games over two injury-filled seasons before they cut him. It was one in a long line of mistakes made by Mike Sherman during his tenure with the dual role of coach and general manager. Johnson never played another down in the NFL after the Packers dumped him in June 2004."

Joe Johnson, like his NBA counterpart, could rack high stat totals in video games, but unlike the future Hall of Fame Jazz forward, this Johnson flamed out too soon.

20 Houston Texans: Brock Osweiler, 2016

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We know how badly this infamous four-year, $72 million contract went, but how does Texans owner Bob McNair feel about the disaster that saw Osweiler traded after only one season? And don't worry, he didn't compare Osweiler to being an inmate.

"We didn't know Brock well enough. Coach (Bill O'Brien) didn't have a chance to get to know him. That's one of the problems with free agency. You need to know who you're dealing with. In the draft, we're able to bring them to Houston, sit down with them, watch them interviewed by a bunch of coaches, and you have time to check them out. You can't talk to them before they become a free agent. You can't work them out. We didn't know him that well."

With the way Deshaun Watson is playing to begin his NFL career, it's safe to say Houston isn't regretting trading their former quarterback, right?

19 Indianapolis Colts: LaRon Landry, S (2013)

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Ryan Grigson made some atrocious moves while serving as the Colts' general manager - and it's hard to praise him for picking Andrew Luck with the top pick in 2012 because getting that wrong would have been like screwing up mashed potatoes - but was anything worse than the LaRon Landry incident? Andre Johnson was a disappointment and Frank Gore has been a mixed result, but PED suspensions and locker room clashes should say everything about Landry's tenure from the Colts from 2013-14.

"The Colts had an incredible locker room last season outside of Landry, who didn't want anything to do with the media or much with his teammates, several people told me last season," ESPN's Mike Wells wrote in 2015. "Landry's teammates went one way and the safety often went the other way. It doesn't work when everybody is not on the same page."

18 Jacksonville Jaguars: Jerry Porter, WR (2008)

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Mistake number one: signing a player who had not been an effective target in four seasons to a six-year, $30 million contract.

Mistake number two: signing a player with MAJOR character concerns to such a deal when previous incidents included throwing a hissy fit after champagne was barred from the Oakland Raiders' training facility and parking in Al Davis' personal spot.

Mistake number three: expecting Porter, with all of the aforementioned incidents and concerns, to play like he was worth this type of money and faith.

Bright spot: Jacksonville realized after only one year of dealing with Porter that he wasn't worth the money and the headache, releasing him and eating up the money. It says something that of the Toby Gerharts and Chad Hennes of the world, Porter is still the winner here.

17 Kansas City Chiefs: Kendrell Bell, LB (2004)

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When the official ESPN report for a free agent signing almost admits the failures of both sides, you have to know the move isn't going to work out.

"Kendrell Bell was having trouble convincing teams he can stay healthy. The Chiefs were having difficulty convincing fans they were getting better on defense after losing out on Samari Rolle and other defensive players. That made Bell and the Chiefs a perfect fit. Bell reached a contract agreement for more than $5 million a year that included $10 million in guarantees. The deal, which is being finalized Tuesday, will be seven years in length."

Did Bell live up to that contract? If you're asking that when he's on a list discussing regretful contracts, I think you know the answer. Bell spent three unproductive seasons in Kansas City before being cut after the 2007 campaign. Yikes.

16 Los Angeles Chargers: David Boston, WR (2003)

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Whether they were in San Diego or Los Angeles, the Chargers have made some questionable free agent moves, but at least guys like Chris Chambers produced in the powder blues. David Boston? On paper, Boston's stats aren't at all bad in his lone season with the Chargers, catching 70 balls for 880 yards and seven touchdowns, numbers that would be enough to warrant Pro Bowl consideration in most years. However, a fight with strength coach Dave Redding and bad practice habits led to a 2004 trade to the Dolphins, where he tested positive for steroids and tore his ACL.

"Let's just say we've got some guidelines here to adhere to,'' Chargers general manager A.J. Smith said in archived articles. "And David wasn't meeting them to our expectations."

15 Los Angeles Rams: Drew Bennett, WR (2007)

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I don't get it. Drew Bennett had one great season with the Titans in 2004 when he caught 80 catches for 1,247 yards and 11 touchdowns, but was average to maybe slightly above average the rest of other five years in Tennessee. Why would the Rams then overpay Bennett on a six-year, $30 million contract? Was it a panic move after they were set to lose Kevin Curtis to the Philadelphia Eagles, or were the Rams being way too optimistic about an offense with Bennett, Steven Jackson, Marc Bulger, and any other weapons they could land in the draft?

Like other teams on this list, it's hard to really point bad free agency moves at the Rams when the reason they've been so mediocre is poor drafting, but Bennett catching 34 balls for 379 yards and three touchdowns in 15 games across two seasons in St. Louis makes him the obvious choice.

14 Miami Dolphins: Ernest Wilford, WR (2008)

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And while I can at least somewhat excuse the Drew Bennett signing because he'd put up solid numbers in the past with the Titans, I don't know what to say about Ernest Wilford - whose career-highs in catches (41), yards (681), and touchdowns (seven) all reeked of a one-year wonder - got a four-year, $13 million contract from Bill Parcells and the Miami Dolphins in February 2008. This was the same offseason that saw the Dolphins use great judgement with the No. 1 overall pick (Jake Long, a great lineman in his first few years) and with landing Chad Pennington when the Jets cut him for Brett Favre.

So, what happened? Wilford caught three passes for 25 yards in seven games for the Dolphins, was converted to tight end the next offseason, and cut before re-signing with Jacksonville for the 2009 season.

13 Minnesota Vikings: Fred Smoot, CB (2005)

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Who wants to talk about Fred Smoot and the Love Boat? Smoot's play in Minnesota was mediocre, sure, but let's talk about the Love Boat scandal where the veteran cornerback, quarterback Daunte Culpepper, and anywhere from 15-20 other players engaged in a sex party during an October bye week in 2005.

Actually, rather than letting us describe what accounts for a Minnesota boat party, we'll instead link you the court summons because there are things in there you absolutely need to read. When the day ends, you really need to hand it to Smoot for making it on this list because so many of these players were either downright awful, battled injuries, or never really fit in. Smoot was out there organizing 'love' parties on boats in the name of team bonding. The Vikings may regret that night, but I doubt Smoot and his female escorts do.

12 New England Patriots: Jonathan Fanene, DT (2012)

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It's obviously rare the Patriots make a splash in free agency, let alone make a move they wind up regretting, so the choices here were either Adalius Thomas or Jonathan Fanene. Thomas didn't quite live up to the major contract he signed in 2007, but he at least made it onto the field and made plays, unlike Fanene who, after signing a three-year deal in 2012, was released in training camp. Why? New England cited Fanene didn't disclose aspects about his medical injury, which makes us wonder why he was even signed in the first place.

Interestingly enough, Fanene was later involved in a lawsuit against the Patriots and team doctor Thomas Gill, who was alleged of helping Bill Belichick create a case for the defensive tackle to be cut and return his $3.85 million signing bonus. Oh, Bill.

11 New Orleans Saints: Adrian Peterson, RB (2017)

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Is this too much of a hot take? Look, all we heard through the entire offseason was how Peterson was going to have a role in the offense alongside Mark Ingram Jr. and rookie Alvin Kamara, but the former NFL MVP was horrifically underutilized before being traded to Arizona for scraps in the form of a conditional pick. What did Peterson do in his first game with the Cardinals? Run for over 100 yards for the first time since December 2015 and win NFC Offensive Player of the Week for his troubles.

I'm not sure what the New Orleans Saints are going to regret more: telling themselves - and by extension, the public - that Peterson was going to have a role, seeing how badly it turned out, and trading him for nothing if Peterson keeps producing like he's 23 again.

10 New York Giants: Chris Canty, DT (2009)

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Why did we pick Chris Canty and not LaVar Arrington when the latter signed a seven-year, $49 million contract with the Giants and only played in six games? Unlike some of these other busts, Arrington at least sustained a career-altering injury in the form of a ruptured Achilles tendon and had to retire the next season AFTER the Giants cut him. That's one of those situations where you regret the injury, not necessarily the contract.

Chris Canty, on the other hand, was a massive disappointment in his four seasons with the Giants on a six-year, $42 million contract. Only twice did Canty play double-digit games, though he was important to the Giants' 2011 Super Bowl run when he had a career-high four sacks. Really, I think the Giants are regretting not getting that type of production over those four years.

9 New York Jets: Curtis Conway, WR (2003)

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Think back for a second to the 2015 NBA offseason when, after meeting with the Dallas Mavericks, then-Los Angeles Clippers center DeAndre Jordan verbally agreed to sign with Mark Cuban and friends. Then, imagine if the Clippers panicked and went out to sign someone like Tristan Thompson or Brook Lopez - decent players, but not quite what Jordan brought to the table. Jordan likely wouldn't have been able to return, right?

More or less, that's what happened with the New York Jets in 2003, who panicked and signed the average Curtis Conway to a three-year deal after learning Laveranues Coles - hey, he appears again on this list! - was likely to sign with the Washington Redskins. Would Coles have returned and brought his explosive ability to the Jets for more years to come rather than Conway, who lasted a lone season in New York?

8 Oakland Raiders: Javon Walker, WR (2008)

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This is one of the more bizzare moments on this list, but when you consider two of the characters involved are Al Davis and Lane Kiffin, it's hard to be surprised. After signing a stuning six-year, $55 million contract with the Raiders before the 2008 season, Javon Walker was consider retiring and returning his $11 million signing bonus, partially becuase of a poor camp and partially from personal issues. Davis persuaded Walker to return and catch 32 balls for 196 yards and a touchdown in eight games before recording no stats in 2009 and being cut in 2010.

So where do Lane and his now-FAU visor come in? Al Davis told everyone that things were fine, but Kiffin told ESPN that he was worried "a lot" about where Walker was at mentally and "maybe they come back and maybe it isn't necessarily for the right reasons." Oh, Lane, stick to commenting on my broken iPhone.

7 Philadelphia Eagles: Nnamdi Asomugha, CB (2011)

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From jogging on plays to reportedly eating lunch in his 1997 Nissan Maxima, Asomugha never quite fit in during his two seasons in Philadelphia from 2011-12. Bleacher Report did a great feature on the All-Pro cornerback earlier this year where he tells his side of the story, but of note is this part.

"'It was interesting that that came out because guys would go home, guys would eat in their car. It’s not an abnormal thing on any team,' Asomugha says, as he starts making eye contact again. 'We’d eat in the training room. We’d eat in the locker room. We’d eat in all sorts of places.' It was too late, though, for Asomugha. And the more he struggled, the more he became the scapegoat for the team’s failures."

6 Pittsburgh Steelers: Ladarius Green, TE (2016)

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Where do we even start with this signing? Green may or may not have lied about his injury history when the Steelers signed him to a four-year, $20 million contract with a $4.75 million signing bonus. Pittsburgh may or may not have never fully investigated Green's history of concussions - or, as the tight end called them in his introductory press conference, "sinus problems" - when he was in San Diego.

Pittsburgh may or may not have gotten too desperate about replacing franchise legend Heath Miller at tight end - a player Green praised when he said “I don’t want to consider myself trying to follow in his footsteps because those are some pretty big shoes to fill." Are the Steelers regretting this signing? Absolutely.

5 San Francisco 49ers: Antonio Bryant, WR (2006)

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Bryant nearly made our pick for the Bengals after they signed him to a four-year, $28 million deal in 2010 before cutting him in the summer after signing Terrell Owens, but Bryant had some major knee issues that had him hobbling and limited in practices. Besides, that contract with Cincinnati was so incentive-heavy that we can let it pass, but it's hard to let Bryant's four-year, $14 million deal with the 49ers slip by.

Coming off a career-year in Cleveland during the 2005 season, Bryant caught 40 passes for 733 yards and three touchdowns in 2006 and was arrested for DUI. Brandon Jacobs had some serious momentum for this spot, as did changing this entry to the Colin Kaepernick saga (but it was realistically either going to be Jacobs or Bryant), but it's the former second-rounder who wins out here.

4 Seattle Seahawks: Matt Flynn, QB (2012)

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Believe it or not, I don't fault the Seattle Seahawks for pursuing Matt Flynn in free agency in 2012, nor do I blame them for signing him to a three-year deal worth $20.5 million...but I do blame them for not having a plan set in stone. Were they going to sign Flynn for that much to compete with incumbent Tavaris Jackson, or was Flynn definitely the starter? If they were going to draft a quarterback, was it going to be someone within the first three rounds who could make a legitimate case, or would it be a sixth or seventh-round player?

Seattle is definitely not regretting drafting Russell Wilson, don't get me wrong, but I do think they're regretting giving Flynn $9 million guaranteed when there was no definitive plan for him to start.

3 Tampa Bay Buccaneers: Derrick Ward, RB (2009)

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Tampa Bay made the right call signing Derrick Ward to a four-year, $17 million deal after the 2008 season. Seriously! Ward had two solid seasons in New York, including pairing up with Brandon Jacobs in 2008 to become the fifth pair of teammates to rush for 1,000 yards in a single season; Tampa Bay was in need of a dangerous running back, so this was a move that made plenty of sense. But, only giving Ward one year on the Buccaneers where he averaged a career-low 3.6 yards per carry on a beat-up offensive line and a struggling offensive line, that's what makes no sense.

True, the Buccaneers were able to get two strong seasons from LeGarrette Blount by way of cutting Ward in 2010, but what was the point? Were they worried he'd start breaking down at 30? Were they just overly paranoid?

2 Tennessee Titans: Michael Oher, OT (2014)

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After five good to great seasons in Baltimore, Michael Oher and his Blind Side (puns!) took their talents to Tennessee on a four-year, $20 million contract. What could go wrong? Well, Oher battled injuries and was graded by Pro Football Focus as the 74th best tackle out of 78 that season. Not good! The next season in Carolina, Oher played in over 98 percent of the Panthers' snaps, allowed a career-low four sacks, and played mostly clean ball when it came to penalties.

So, which should the Titans regret more: letting Oher go way too early, or even signing him to such a contract in the first place? Given Oher's career could potentially be over after injuries and concussion issues, you could pick either of those and have a legitimate gripe...

1 Washington Redskins: Albert Haynesworth, DT

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Alright, Albert, do you want to plead your case about what really happened in Washington? In a 2015 letter to himself on The Players Tribune, Haynesworth did exactly that.

"You will lose your passion for football in Washington, and it will be impossible to get back. If nothing else, listen to me on this, Albert: Do not leave the Tennessee Titans. Your defensive coordinator Jim Schwartz is a mastermind. No matter how much I tell you this, you’ll probably never realize it until your career is over, but it’s true. You’re like a system quarterback. You thrive in a very specific scheme."

Still, I don't think that's enough to make the Redskins handing you a major contract only to see you play lethargically, get into fights, and fail your conditioning test. But, there's a positive! At least you weren't hired from a bingo home to call plays.

Which of these free agent signings do you think teams are regretting the most? Make sure to let us know in the comment section below!

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