Being a general manager is incredibly difficult.

Tasked with building a championship-worthy team, these executives do their best to balance tough financial questions.

Should you commit to Player X as the cornerstone of the roster? Are you willing to spend that much on a free agent? The market rate is high for a quarterback, but is that signal-caller actually worth the money?

Cap sheets for NHL franchises are nearly in nine figures, while some MLB and all NBA and NFL organizations are soundly in the hundreds of millions. Because of that enormous ability to spend, however, the glaring mistakes also become terribly expensive, too.

The list is subjective but considers a player's contract value relative to salary cap, along with a consideration of cost versus production and—for active deals—future outlook.

Players presented in alphabetical order.

Javier Baez

Javier Baez rose to prominence as a slick-fielding shortstop with the Chicago Cubs, playing a key role on the World Series-winning team in 2016 and finishing as the National League MVP runner-up in 2018.

The problem is Baez has never seen a breaking ball he believed was untouchable. Pretty easy to strike out that way.

And, my friends, that approach hasn't aged well.

Prior to the 2022 season, Baez inked a six-year, $140 million contract with the Detroit Tigers. Through the 2024 campaign, though, he's trudged to a .221 average and .262 on-base percentage while striking out 114 times per season compared to just 21 walks.

Miguel Cabrera had a miserable deal in the final years before his retirement, but he was a bona fide legend in Detroit.

Baez is simply an expensive mistake.

Bradley Beal

Extending a max contract offer is dangerous enough. Doing so while attaching a no-trade clause is inviting a disaster.

Unfortunately for the Washington Wizards, a five-year, $251 million pact for Bradley Beal turned sour quickly. Fortunately for the Wiz, they managed to unload him on the Phoenix Suns—who, as of this writing, aren't not looking to trade away the veteran guard.

Beal has averaged about 18 points in his time with Phoenix, a number far below expectations for someone making $50 million annually.

Whatever the future holds for Beal—and wherever that may be—this albatross of a contract runs through the 2026-27 season.

Kirk Cousins

Hey, I was wrong, too. When the Atlanta Falcons signed Kirk Cousins during the 2024 offseason, I applauded the move.

By the end of the year, he was benched.

Hindsight does not help, considering Atlanta signed him in March and used a first-round pick on Michael Penix Jr. in April. It seemed the Falcons had made a long-term commitment to Cousins with a four-year contract with $100 million in guaranteed money and a no-trade clause, so that selection was a surprise.

As it turns out, the Falcons gave themselves a backup plan and needed to use it quickly. Cousins threw 18 touchdowns to a league-worst 16 interceptions, and Atlanta went 7-7 in his 14 starts.

The team is expected to move on from Cousins at some point during the 2025 offseason.

Daniel Jones

On the other hand, I never liked Daniel Jones' extension.

(Harsh, sure. But someone whose career earnings top $100 million can check his bank account and laugh me away.)

In 2023, the New York Giants offered him a four-year contract with $82 million of the $160 million guaranteed. Jones had flashed some competence as a runner in 2022, and the Giants—who'd declined his fifth-year option—extended his deal during the ensuing offseason.

The nightmare scenario wasted no time.

Even before a knee injury ended his season, Jones' passing efficiency and interception rate tumbled to career-worst rates. He returned in 2024 but continued to struggle; the Giants surpassed 20 points in only three of his starts on their way to a 2-8 record and his benching.

Jones' role devolved to playing scout-team safety, and then he requested a release that was granted.

Jonathan Huberdeau

In terms of total dollar value, Jonathan Huberdeau isn't in the same neighborhood as NBA or NFL players. He's also put together a legitimate surge in the 2024-25 season, reclaiming a bit of respect.

He's climbing out of quite a perception hole, though.

After the Calgary Flames acquired him in the 2022 offseason, they signed him to an eight-year, $84 million agreement. Huberdeau had just amassed 115 points with a league-leading 85 assists on the Florida Panthers, where he'd developed into an All-Star winger.

During his first year, however, his production tanked to 55 points. Huberdeau tallied only 52 points in 2023-24 despite notching at least 79 appearances in both seasons.

That wouldn't be terrible for an average second-line player, but he's getting paid superstar money. It also doesn't help that the player he was traded for, Matthew Tkachuk, led the Panthers to a Cup last season.

Calgary is desperate for Huberdeau to reclaim his previous form.

Paul George

Too soon? I can entertain that argument.

The first season of Paul George's four-year, $211 agreement with the Philadelphia 76ers only recently hit the halfway mark. In other words, 87 percent of this contract is still out there.

But for Philly fans watching this frustrating first year, that particular number is also a bit haunting.

Injuries alone are unfair to criticize. Simultaneously, it's fair to recognize that PG arrived with a history of health setbacks, playing no more than 56 games in four of his five seasons with the Los Angeles Clippers. George's availability has already waffled with the Sixers, too.

The greater issue is PG's production has dropped; he's averaging about 17 points here in late January.

Similar to Beal, that's simply not reflective of a $50 million player. If the trend continues, the last three seasons of George's contract will become a mess for Philly to navigate.

Jamal Murray

Jamal Murray, like Beal and George, is a good player. None of their inclusions are meant to suggest they aren't talented.

The problem, again, is cost vs. production.

Shortly before the 2024-25 campaign began, Murray inked a four-year extension worth $208 million with the Denver Nuggets. That maximum deal effectively locked him in as the sidekick to Nikola Jokic, and Murray's efficiency has dipped noticeably over the last calendar year.

Additionally, similar to George, this contract is a major gamble on a player with questionable durability.

Murray made 75-plus appearances during his first three seasons yet hasn't topped 65 in the last half-decade. The current year is fine—knock on wood or whatever you need—but the trend is concerning.

Denver needs Murray's shooting range to endure, and more consistency as a secondary playmaker certainly would not hurt.

Ben Simmons

At his peak, Ben Simmons looked like the kind of player who should command a maximum deal. He never had shooting range but played elite defense, showed great passing vision and could rebound well.

So, when the Sixers offered a five-year, $180 million extension, it seemed the positives could outweigh a glaring negative.

Whoops.

Simmons had a decent first season on the contract but didn't play in 2021-22 because of a back injury and holdout. Philly sent the disgruntled guard to the Brooklyn Nets, where Simmons didn't even hit 82 games played until his third season with the organization. In those appearances, he's mustered less than seven points per game.

When the 2024-25 campaign ends, the oft-injured Simmons will head to unrestricted free agency.

Deshaun Watson

Nothing about this contract has aged well.

Deshaun Watson didn't play in 2021, partly due to a holdout and mostly because of sexual harassment allegations. After that season, the Cleveland Browns shipped six draft picks to the Houston Texans for Watson and immediately signed him to a fully guaranteed five-year, $230 million pact.

Through three seasons, it's been a debacle.

Watson served an 11-game suspension in 2022, and a shoulder injury limited him to six games in 2023. Watson struggled in 2024 before a right Achilles tear sidelined him after seven starts, then he re-tore that Achilles during recovery and could miss the entire 2025 season.

Cleveland holds the No. 2 overall pick in the 2025 NFL draft, so it's possible the Browns begin to build around a rookie QB and move on from the forgettable Watson era.

Russell Wilson

Russell Wilson was a legitimate star for the Seattle Seahawks in portions of his 10 seasons with the team. He helped the Seahawks win a Super Bowl and appear in another.

When the relationship soured, Seattle dealt him to the Denver Broncos with a five-year, $242.5 million extension to sign there.

Obviously, you realize where this is headed. Wilson had a disappointing debut season, then the Broncos hired Sean Payton. The team embraced a teardown after Payton's first year in 2023, releasing Wilson despite the $85 million in dead money attached to the move.

The bright side for the Pittsburgh Steelers is they picked up Wilson for $1.1 million—Denver was on the hook for the rest—and he started 11 games on the franchise's path to the postseason.

However, the Steelers collapsed down the stretch in 2024 with five straight losses while scoring no more than 17 points.

And it became clear, once again, why Payton and the Broncos moved on from Wilson in the first place.