Free agency is a losing game. The nature of paying market value for players in a league where the salary cap is rapidly rising dictates that teams will rarely find value when signing players in the spring. The vast majority of valuable contracts around the league belong to players who are still on their rookie deals, and while a rare exception like Justin Forsett might slip through the cracks, most free agents are going to be signing deals paying them more than they would get as a draftee entering the league.

Even logical moves for talented players can go awry. Look at the Buccaneers, who shopped at the top of the market last season and came away with former Bengals Anthony Collins and Michael Johnson. The two were guaranteed a combined $27 million and signed to fill critical holes on Tampa Bay’s roster, with Collins taking over at left tackle and Johnson serving as the team’s top defensive end. They were a disaster, and after one season with the Bucs, they were both released this past week. They wouldn’t have appeared on last March’s lists of the offseason’s worst signings several days into free agency, but they ended up as arguably the two biggest mistakes.

Imagine, then, just how bad it must be if a move seems obviously egregious on the surface just days after the ink has dried. The worst deals from free agency, even before we see how players and teams mesh, involve some combination of misguided logic and desperation. Organizations ignore opportunity cost and laugh at history as they fall in love with players who are unlikely to live up to lofty expectations. It’s a messy enterprise, and the whole thing works out just frequently enough to convince teams that they might actually be the ones to get it right in 2015.

Let’s run through the 10 worst deals I’ve seen so far in free agency. The players are of varying skill levels and the deals are of varying sizes, so consider the former in relation to the latter. A $20 million mistake is worse than a $5 million mistake, but the $20 million player is also more likely to stick around as somebody competent, while the $5 million player may very well be off the roster in eight months if he fails to live up to expectations. Let’s begin with a deal completed before the league year opened as part of the most depressing arms race in recent memory:

Josh McCown to Cleveland

Contract: Three years, $14 million, $6.25 million guaranteed

It’s stunning to think that a team could make this very same mistake in consecutive seasons. For years, McCown was a lower-echelon backup making something close to the veteran’s minimum. He caught on with Marc Trestman’s Bears and delivered one of the finest small-sample flukes you’ll ever see, with an unsustainably low interception rate driving a 224-pass sample that made him look like Peyton Manning.

The Buccaneers gave him a two-year, $10 million deal last offseason in the hopes that those 224 passes meant more than his 1,113 preceding replacement-level throws. They were wrong. McCown’s interception rate spiked, his completion percentage fell back to its previous totals, and he took sacks (thanks, Anthony Collins) at an alarming rate. He went 1-10, got hurt, and the Buccaneers finished with the NFL’s worst record.

Instead of recognizing that the wrong guy off the scrap heap could play well in a small sample and therefore looking for the right guy off the scrap heap, the Bucs and now the Browns are paying McCown like he’s a meaningful asset. Cleveland beat Buffalo in a bidding war for McCown, who actually got a whopping $6.25 million in guaranteed money.

Why on earth would you give McCown that much guaranteed money? What are you paying for? Veteran competence? McCown has been about the 50th-best quarterback in football for the vast majority of his career. He just finished a season as the starting quarterback on the worst team in football with the worst offense in football despite a pair of pretty great receivers. What sort of certainty are you paying for? How much worse can a guy making the league minimum be than the worst of the worst?

The Browns will surely claim they signed McCown to mentor Johnny Manziel, but that’s a ridiculous sum of money to give for the sake of mentoring. There’s another word for mentoring — it’s coaching, and two years ago the Browns had a coach with a great history of tutoring successful quarterbacks. They parted ways with Norv Turner then, and it’s no coincidence that his new pupil — Teddy Bridgewater — looks like the best quarterback from the 2014 class.

Al Pereira/New York Jets/Getty Images

David Harris Stays With the Jets

Contract: Three years, $21.5 million, $15 million guaranteed

At his best, Harris was a dominant gap-plugging inside linebacker who was just on the edge of being good enough against the run to justify Pro Bowl consideration. He slipped a bit during the slow burn of the Rex Ryan embers, but Harris remains effective enough against the run to justify an existence as a three-down linebacker. At 31, you would expect him to be on the downside of his career, but it still seemed logical for the post–Kiko Alonso Bills to target Harris as a Ryan acolyte in free agency.

The Jets ensured that wouldn’t happen by massively overpaying to keep Harris in town. Harris’s three-year deal pays out $15 million in guaranteed money over the next two seasons, a deal that stands out as an outlier among similar players. Harris comes away with the fourth-largest guarantee for an inside linebacker, and no veteran with a contract as big as Harris’s has a larger percentage of his money guaranteed. And this comes for a guy who was declining!

Gang Green is surely celebrating the arrival of Darrelle Revis, a truly transformative player. But Harris, at this point in his career, just isn’t effective enough to justify the hefty tag. Even if the Jets were afraid of losing Harris to Ryan’s Bills, they could have signed a similarly skilled run defender in Brandon Spikes and paid him a fraction of what they’ll be paying Harris.

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Frank Gore to Indianapolis

Contract: Three years, $12 million, $7.5 million guaranteed

Would our entire opinion of Colts GM Ryan Grigson be different had Vick Ballard just stayed healthy? Grigson found a useful running back in Ballard during 2012, and if Ballard hadn’t torn his ACL early in 2013 and his Achilles in July 2014, the Colts wouldn’t have traded a first-round pick for Trent Richardson and wouldn’t have had to stretch Ahmad Bradshaw in 2013 or 2014.

Even though Richardson failed miserably and Bradshaw has been a useful player at close to the veteran’s minimum the past two seasons, Grigson doubled down on his running back spending and convinced Gore to leave Philadelphia at the altar. I’ve seen reports that the guaranteed money in this deal is anywhere between $6.5 million and $8.5 million, but in either case, it’s still a staggering sum of money for a running back who is about to enter his age-32 season.

Just 11 running backs since the merger have carried the ball 200 times in their age-32 season, and they collectively haven’t been very good, averaging 3.8 yards per carry. That club drops to five at age 33, and the only guy to do it since the second Clinton administration was Emmitt Smith. That’s a group that includes four Hall of Famers, and even they could muster only 3.7 yards per carry. Gore can still pass block and his patience as a runner is otherworldly, but his work as a receiver has dwindled to virtually nothing. He doesn’t need to get 200 carries to justify his roster spot, but the Colts won’t return value with this sort of contract unless he does.

Furthermore, it’s bizarre that Grigson didn’t structure the deal in a way to get the vast majority of the guaranteed money out of the way in 2015, before Andrew Luck’s cap figure skyrockets with his fifth-year option and eventual massive contract extension. Gore’s cap figure will be $4.5 million in 2015 and $4 million in 2016 before a $3.5 million base salary he’s unlikely to see in 2017. Gore might have retired after 2015 if he saw more money in the first year of the deal, but then again, that might have been a feature as opposed to a bug.

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Byron Maxwell to Philadelphia

Contract: Six years, $63 million, $25.5 million guaranteed

I wrote about the Maxwell deal earlier this week. It’s not that Maxwell is a bad player, of course, but that the Eagles are paying him like he’s one of the league’s best cornerbacks out of sheer desperation in a thin cornerback market. The absolute best-case scenario is that Maxwell lives up to this deal, but these kinds of contracts almost always turn out to be mistakes.

LeSean McCoy to Buffalo

Contract Extension: Five years, $40 million, $26.5 million guaranteed

I also wrote about the McCoy deal in that same column. McCoy wasn’t technically a free agent, but I’m going to sneak him in here. How a running back with no leverage managed to get this big of a contract extension from the Bills is a lesson in how bad organizations operate.

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Dan Skuta and Davon House to Jacksonville

Skuta Contract: Five years, $20.5 million, unknown guaranteed

House Contract: Four years, $25 million, $10 million guaranteed

The Jaguars have had to shop in weird places to get people to take their money this offseason. It’s understandable, even as an overpay and as perhaps the only team bidding at that level, to give Julius Thomas $21 million guaranteed in a five-year deal. You can justify giving Cowboys backup tackle Jermey Parnell $13 million guaranteed in a five-year deal, if only because there was a market for his services at that price and your right tackles nearly got Blake Bortles and Chad Henne killed last year. Those deals aren’t great, but there’s some logic behind them.

What about Skuta and House, though? Skuta was a reserve outside linebacker behind Aldon Smith in San Francisco who showed flashes of effectiveness as a pass-rusher in Smith’s absence last year, contributing five sacks. (He also recorded zero sacks in eight starts in 2013.) At 28, he doesn’t have much room to improve, and the Jaguars already had the league’s second-best pass rush last season with the likes of Chris Clemons and Ryan Davis playing meaningful roles. Maybe Skuta is a hidden superstar. More likely, he’s a rotation guy getting paid meaningful money while keeping the Jaguars from possibly stumbling on another guy like Davis, who would be as effective for the veteran’s minimum.

There was more of a market for House, a reserve cornerback with Green Bay who just crosses the magic 6-foot barrier that’s gotten cornerbacks paid this offseason. The structure of the deal is still unclear, but what I don’t understand is the logic behind bringing in a guy like House instead of developing a cornerback. Wasn’t the point of bringing in Gus Bradley that he was going to be able to replicate the Seattle defense, a unit built on young talent from the draft? The Seahawks finished up their Super Bowl–winning defense by adding Cliff Avril and Michael Bennett on short-term deals, but they built its core over the two previous seasons by drafting and developing their picks. The Jaguars brought in David Caldwell to draft young talent and Bradley to develop it, things they did well at their last gigs. At what point does signing low-ceiling free agents get in the way?

There’s a school of thought that bringing in competency allows the few young talents the Jaguars do have to develop, and maybe that will be true. I know my colleague Robert Mays argued that this is what the Jags had to do, but I respectfully disagree. Maybe Dwayne Gratz will be better if he has to compete with House for a starting job. More likely is that the Jaguars will reach for mediocrity with these signings and find themselves disappointed — and without options — when they get there.

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Jonathan Casillas, Dwayne Harris, and J.T. Thomas to New York Giants

Casillas Contract: Three years, $8 million, $2.975 million guaranteed

Harris Contract: Five years, $17.5 million, $7.1 million guaranteed

Thomas Contract: Three years, $12 million, $4.5 million guaranteed

I can piece together a logic in Jacksonville’s moves, even if I don’t necessarily agree or think that it’s settling for competency. I wish I could find the same strand of sense in what the Giants have done over the past few days. My vaguest guess is that they’re trying to improve their special teams, but they weren’t even all that bad on special teams last season, finishing 15th in DVOA. In each case, they’ve paid a premium for almost the definition of a replacement-level football player.

Casillas won a Super Bowl ring with the Patriots last year as a reserve linebacker after starting his season in Tampa Bay, which is just about the biggest upgrade you can imagine a football player making over the course of a season. (Sorry, Logan Mankins.) He started three games for the Patriots but played nearly as many special teams snaps in New England (145) as he did on defense (158). He’s a perfectly competent coverage guy on special teams and could profile as a backup linebacker, but you should be able to find those guys in the draft every year (or find them for close to the minimum) without having to pay them guaranteed money.

The deal for Thomas isn’t much different. Again, he’ll fill in as a special-teamer and should compete for a job as an outside linebacker. He was an anonymous member of Jacksonville’s defense over the past three seasons. The Giants committed $7.5 million in guaranteed money to him and Casillas when, elsewhere, it took the Patriots just $5.5 million in guaranteed money to nab Jabaal Sheard, a legitimate pass-rusher who would have played defensive end in New York. Bill Belichick is surely confident he can go out and find a special-teamer who will make the minimum. Why can’t GM Jerry Reese do the same?

The deal for Harris is probably the worst of the three. He was the lead return man in Dallas over the past four years, and while he had an excellent 2013, Dallas was below-average on kick returns and punt returns in 2014. At 27, Harris offers virtually no upside as a receiver. Furthermore, there’s little reason to think that the market for return men is such that the Giants couldn’t find a similar player at a fraction of the cost. They had Trindon Holliday, who looked like a superstar for a year in Denver, in camp last offseason before cutting him. The best return men in football last year were guys like Adam Jones, Jacoby Jones, Darren Sproles, and Julian Edelman, all of whom were once available for close to nothing.

Over the past two seasons, Reese has shown a similar propensity for giving replacement-level talent meaningful money as part of long-term contracts. Last year, it was guys like Rashad Jennings, J.D. Walton, and O’Brien Schofield (who had his contract annulled when he failed a physical). Where was the market to give Harris this much money? Was somebody really going to give him $6 million guaranteed and Reese had to top it? I can’t fault Reese too much as a scout, but in terms of valuing talent, it’s hard to justify the moves he’s made in March in recent years. You can kiss the rings only so many times.