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15 Offseason Moves These NFL Teams Will Regret

Some sports fans out there see Memorial Day weekend as the time of the year when the National Hockey League and National Basketball Association seasons begin to come to an end, and also when the good part of the Major League Baseball campaign gets underway. For those of us out there who love the National Football League, however, the end of May means we are only a few months away from football being back on television. Now that the majority of high-name free agents have been signed by clubs and the 2017 NFL Draft is well behind us, we can begin to evaluate roster decisions and transactions made by teams in the months following the New England Patriots defeating the Atlanta Falcons to win Super Bowl XL.

Every NFL franchise – yes, even the Patriots – will get things wrong over the course of an offseason, and there will be teams filled with certain levels of regret come the holiday season. While the perception exists we cannot truly grade any team's draft class until years down the road, we are able to make educated guesses about offseason moves that will leave certain executives and coaching staffs questioning themselves before the start of Week 17. Several would-be championship contenders made some curious decisions during the spring. Will any, or even all, of those teams fail to achieve the goal of winning the Super Bowl next February because of those moves? Which of the teams spotlighted in this piece will want a complete re-do of the offseason once January 2018 begins?

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15 San Francisco 49ers: Giving Brian Hoyer the Keys to the Offense

Benny Sieu-USA TODAY Sports

Some may say the San Francisco 49ers know exactly what they're doing in making journeyman quarterback Brian Hoyer the starter for a team that's likely to lose more games than it will win later this year. That's a risky decision to make in this “what have you done for me, lately?” business.

Hoyer can be a fine backup for a team with an established QB running the offense, but placing him atop the depth chart before the start of the 2017 season will be a sign the Niners are already looking ahead and hoping next year's draft class will be as stellar as advertised. For what it's worth, Colin Kaepernick is roughly two years younger and has a better overall resume than Hoyer. Then again, the Browns aren't regretting tanking in 2016; yet.

14 Carolina Panthers: Paying Matt Kalil

Bruce Kluckhohn-USA TODAY Sports
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Carolina Panthers quarterback Cam Newton will be hoping we're wrong about this one. Offensive tackle Matt Kalil failed to impress during the past several seasons, and he missed the majority of the 2016 campaign because of a hip injury. Carolina must've seen something the club liked in film sessions, though, as the Panthers gave him a five-year contract that could be worth over $50 million.

The dead cap value of that deal decreases from $13 million in 2017 to $9.6 million next year, meaning the Panthers are banking on Kalil being healthy and playing as well as he did during the first two years of what appeared, at the time, to be a promising career. Otherwise, Carolina will regret this investment even before the start of the 2018 season.

13 Kansas City Chiefs: Drafting Patrick Mahomes II

Denny Medley-USA TODAY Sports

The Kansas City Chiefs acquiring a young quarterback to sit behind Alex Smith would've been fine, but the Chiefs didn't need to trade up and mortgage multiple draft picks to do so just for Patrick Mahomes II. Whatever you think of Mahomes, Smith is only 33 years old, and he has played well throughout the majority of his time with the Chiefs.

Nobody is going to confuse Smith for Tom Brady or Cam Newton, but the Chiefs nevertheless could've trusted Smith to win games and concentrated more on adding talent to both sides of the football up until the veteran is set to enter free agency after the 2018 campaign. At this rate, the Chiefs would have to start Mahomes and get something for Smith in a trade to not regret this move.

12 New Orleans Saints: Trading Brandin Cooks

Mark J. Rebilas-USA TODAY Sports
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We offer the following warning for all NFL teams out there: If the New England Patriots call you up about trading for one of your wide receivers, they probably aren't doing you a favor or trying to be nice. Drew Brees turned 38 years old this past January, meaning every season he is still able to take the field is a blessing.

Trading Brandin Cooks, a player the Saints drafted in 2014, would probably be logical if those running the club were punting on the upcoming season and preparing to reset, but that's no way to treat a franchise legend who will be enshrined in the Pro Football Hall of Fame next decade such as Brees. Unless Tom Brady fails to make good use of Cooks, something we don't see happening, the Saints will regret this deal.

11 Pittsburgh Steelers: Drafting T.J. Watt

Brian Spurlock-USA TODAY Sports

This has little do to with T.J. Watt, a linebacker who may prove himself to be known for something other than being the brother of superstar J.J. Watt. The offense of the Pittsburgh Steelers could've used a tight end ready to contribute starting this fall, and three players at the position were drafted before the Steelers took Watt late in the first round.

Knowing all we know now, it seems the Steelers would've been better off moving up and drafting O.J. Howard. While we normally believe tight ends can be found on the second and third days of drafts, quarterback Ben Roethlisberger isn't getting any younger, and he's recently hinted retirement is on his mind. We would've given Big Ben another target on the first night of the draft.

10 Los Angeles Chargers: Paying Russell Okung

Isaiah J. Downing-USA TODAY Sports
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According to Spotrac, the Los Angeles Chargers have $25 million in dead cap space tied up on offensive tackle Russell Okung after signing him during the offseason. That value goes down, slightly, to $19.5 million for the 2018 campaign. Giving Okung such a deal would've made sense in March 2013, but that was four years ago.

There are no signs he can again be the player of old and the force up front that he was after he made the Pro Bowl in 2012. In fact, the Chargers may have to consider themselves lucky if Okung is able to remain healthy for the entire 2017 season. Credit to Okung for landing such a massive deal, but we think the Chargers are going to regret this one sooner rather than later.

9 Dallas Cowboys: Not Filling Secondary Holes

Matthew Emmons-USA TODAY Sports

Don't look now, but the Cowboys got worse, not better, following the team's outstanding 2016 season. Morris Claiborne, a Dallas draft bust, will look to resurrect his career with the New York Jets. Brandon Carr has moved on to the Baltimore Ravens. J.J. Wilcox signed with the Tampa Bay Buccaneers. Last but not least, Barry Church joined the Jacksonville Jaguars.

Dallas signed Nolan Carroll during the offseason, but the 30-year-old is, seemingly, no longer at his best. The Cowboys also used their first-round pick on defensive end Taco Charlton, who could be a solid player in his first year in the NFL but who won't be in the Dallas secondary. The Cowboys may regret not filling these roster gaps once they line up against an improved New York Giants passing attack.

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8 Denver Broncos: Not Trading For or Signing a Veteran Quarterback

Ron Chenoy-USA TODAY Sports
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Who, exactly, is going to start at quarterback for the Denver Broncos later this year? The fact that we are asking this question less than a week before the unofficial start of the summer says plenty about the signal-callers on the team's roster. Adding Tony Romo, either via free agency or a trade depending on Romo's situation, seemed the logical move for a Denver club in need of a proven product at the position for at least one more year, but the Broncos decided to not pull the trigger on that transaction.

Denver also opted to trust that either Paxton Lynch or Trevor Siemian will silence critics and take hold of the team's offense. If that doesn't happen, the Broncos will be left with much regret at the end of the 2017 season.

7 Chicago Bears: Quarterbacks

Patrick Gorski-USA TODAY Sports

The Chicago Bears needed to find a replacement for Jay Cutler, which is why it made all kinds of sense when the team awarded free agent Mike Glennon with a contract and an opportunity to start later this year. Then, for reasons that go beyond logic, the Bears traded up on the first night of the draft to select Mitchell Trubisky.

A quarterback competition is not what Glennon needs at this stage of his career, as he's now in a position similar to what he experienced when he was with the Tampa Bay Buccaneers before the Bucs drafted Jameis Winston. Even if Trubisky manages to become a future star and franchise QB, which isn't guaranteed, it's difficult to see the logic in Chicago's path toward acquiring the product out of North Carolina.

6 Cleveland Browns: Letting Terrelle Pryor Go

Geoff Burke-USA TODAY Sports
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Yes, the Cleveland Browns had a horrendous and historically-bad 2016 campaign, during which the team nearly went 0-16, but Cleveland has, truth be told, made several positive moves during the offseason. Nevertheless, allowing quarterback-turned-wide receiver Terrelle Pryor to leave via free agency and eventually sign with the Washington Redskins made no sense.

The Browns began the offseason with all kinds of cap space, the team's offense needs a weapon such as Pryor and Cleveland ultimately replaced Pryor with Kenny Britt, a move that may be a downgrade when all is said and done. Cleveland will regret losing Pryor if he becomes a favorite target of Washington quarterback Kirk Cousins, as the tremendous athlete who can stretch the field could have done wonders for Cody Kessler during Kessler's second year with the Browns.

5 Cincinnati Bengals: Offensive Line

Sam Greene/Cincinnati Enquirer via USA TODAY NETWORK

Here's an interesting thought we didn't think we'd have at the start of 2017: It's possible the Cincinnati Bengals will be the worst team in the AFC North later this year. The Cleveland Browns (probably) won't be NFL laughingstocks forever, but the Bengals failed to fill some significant roster holes during the offseason.

Veteran offensive tackle Andrew Whitworth signed with the Los Angeles Rams following the 2016 campaign, and 27-year-old guard Kevin Zeitler inked a deal with division rivals the Browns. The Bengals, meanwhile, decided they didn't need to address offensive line in the draft. Even if first-round pick wide receiver John Ross is a hit right out of the gates, it won't matter much if quarterback Andy Dalton is running for his life during games.

4 New York Jets: QB?

Ed Mulholland-USA TODAY Sports
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Unless we are missing something as of the final days of May 2017, it appears people in charge of the New York Jets are going to try to sell journeyman Josh McCown as the team's starting quarterback ahead of the likes of Bryce Petty and Christian Hackenberg on the depth chart.

The Jets probably wouldn't be winning a division title even if the team made a massive immediate upgrade at QB, but somebody out there has to be a better option than a veteran who will turn 38 years old during the summer and who hasn't been able to consistently remain healthy in recent years. Colin Kaepernick is a name that comes to mind. Heck, Jay Cutler may be available unless he decides he wants to go all-in on a television career.

3 Washington Redskins: Treatment of Kirk Cousins

Geoff Burke-USA TODAY Sports

Whenever a casual or diehard sports fan makes a comment about how there is no longer any loyalty in sports, he or she is probably referring to a player leaving a team in order to sign a bigger contract with a different franchise. Quarterback Kirk Cousins serves as a reminder why players should work to get whatever they can during their brief careers.

For the second straight offseason, the Washington Redskins placed the franchise tag on Cousins, essentially telling him, in the process, he needs to work to earn a long-term deal even though he's the best QB Washington has started this decade. It's only a matter of time before this situation leads to feelings of resentment and affects the team's locker room. We believe Washington may regret disrespecting Cousins later this year.

2 New York Giants: Trusting Ereck Flowers

Scott R. Galvin-USA TODAY Sports
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The New York Giants had a solid offseason, on paper, but those running the club curiously decided they still trust Ereck Flowers will become a dependable left tackle even though he has routinely struggled during his first two seasons in the NFL. Flowers was nothing short of a liability when tasked with protecting two-time Super Bowl MVP Eli Manning, particularly during big games and the team's playoff loss to the Green Bay Packers this past January.

Big Blue passed on upgrading at the position via the draft or free agency, a move General Manager Jerry Reese and head coach Ben McAdoo both may regret if Manning is unable to get up after taking a shot delivered by a pass-rusher who toasts Flowers during a game. Reese and McAdoo had better be right about the third-year pro.

1 Indianapolis Colts: Not Protecting Andrew Luck

Thomas J. Russo-USA TODAY Sports

The Indianapolis Colts squandering the talents of Andrew Luck will be one of the biggest wastes in NFL history if the club doesn't get things right regarding the QB who has Hall-of-Fame talent. Indianapolis elected to not draft a single offensive lineman until the fourth round of the 2017 NFL Draft even though it seems obvious to national pundits Luck could use some extra protection.

Indianapolis failing to surround Luck with adequate help on offense and up front has become a weird NFL tradition, and that tradition continued this past offseason. Luck underwent shoulder surgery earlier this year to fix a problem he had dealt with since 2015. It's not an overstatement to suggest there are concerns about his ability to remain healthy playing behind his current line.

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