The Worst Contracts Ever Signed in US Sports History

Worst Contracts in the History of American Sports

The Oakland Raiders selected JaMarcus Russell first overall in the 2007 NFL Draft, eventually inking him into a six-year deal worth $63 million.

Unfortunately, things didn’t pan out, as Russell was let go by the Raiders after three horrendous seasons and a whole bunch of headaches.

I bring this “error in judgment” up because it wasn’t the first time a professional sports organization handcuffed themselves by signing a player to an atrocious deal.

And by golly, it won’t be the last.

There were a lot of candidates who were up for nomination, and narrowing it down wasn’t easy. But after diligent research, a bit of head scratching, and lots of laughs, here are what I believe are the eight worst contracts in the history of American professional sports.

Jay Cutler – Chicago Bears

  • Deal: 7 Years, $126 Million

Jay Cutler went 5-6 as the starting quarterback for the Bears during the 2013 NFL season, yet the Chicago franchise wasted absolutely no time making sure he would be staying in Chicago for the foreseeable future.

The Bears lengthened Cutler’s deal, giving him a $126 million extension that was supposed to last until 2020. So why is Mitchell Trubisky currently the man under center in Chi-Town?

I’m willing to overlook the part about Jay profiting off of his wife’s hit series, Very Cavallari, which premiered in July of 2018. But I can’t excuse what Jay did on the field during his time in the Windy City.

Straight after signing that mega-extension, Jay guided the Bears to a 5-11 record in 2014 and threw a league-high 18 interceptions. Remember that at this time, Cutler was making more money than Tom Brady, Ben Roethlisberger, and Philip Rivers.

Chicago improved to six wins in 2015 but still came nowhere near reaching the postseason. Once 2016 arrived, Jay really started depreciating as an NFL quarterback, in part due to sustaining a labrum injury in his right shoulder. By 2017, Chicago realized that Jay was no longer a suitable starting quarterback in the National Football League and wound up releasing him in March.

By May, Cutler had announced his retirement and agreed to be a commentator for FOX Sports.

Let’s forget about his failed comeback attempt in Miami and focus on what the Bears got out of the deal. They grossly overpaid a declining QB 126 million bucks to play for seven years.

Instead, Cutler delivered an 18-31 record over parts of four seasons and turned into a punchline of NFL jokes.

Josh Hamilton – Los Angeles Angels

  • Deal: 5 years, $125 million

Josh Hamilton won the AL MVP Award in 2010 and swatted 43 homers in 2012. There was never any doubt as to how powerful of a hitter Hamilton was, which is why the Angels jumped on the opportunity to add him to their roster after the 2012 season was completed.

Despite years of battling drug addictions and several off-the-field issues, the Angels felt like they could surround Josh with a positive atmosphere. Keep in mind that Josh ended the 2012 season with a career BA of .304 and was one of the most feared hitters in Major League Baseball.

It was understandable that the Angels agreed on a 5-year/$125 million deal, but that doesn’t mean things would work out.

Josh hit a paltry .250 during his first year in Anaheim and saw his slugging percentage dramatically drop from .577 to .432.

Injuries held Hamilton out of more than 70 games in 2014, and his numbers again reflected an average hitter at best. Shoulder surgery in early 2015 was the beginning of a downward spiral that would ultimately destroy his career with the Halos.

While rehabbing the AC joint in his right shoulder, Josh relapsed and was deemed unfit to play. Although there was more than $80 million and three years left on his deal, the Angels ownership was keen on letting him walk.

By the time April was over, Hamilton was traded back to Texas for essentially nothing in return.

The Angels didn’t have to cough up the full amount ($125 million), but it’s not like they got off cheap, either.

For the two or so years Josh was in an Angels uniform, owner Arte Moreno sadly compensated Josh Hamilton with $68 million.

Rick DiPietro – New York Islanders

  • Deal: 15 years, $67.5 Million

The New York Islanders were convinced that Rick DiPietro was going to be the greatest goalie in the NHL for a long time to come. How else can you explain the idiocy behind signing a 25-year-old kid to a 15-year deal?

Did they really think that Rick was going to be effective as a 40-year-old goaltender in the National Hockey League?

Allow me to point out what DiPietro achieved post-2006, and we’ll find out if he lived up to the hype.

Well, he went 26-28 during the 2007/2008 season, which isn’t as bad as it sounds when you find out what happened next. Rick played a total of just 50 games from 2008-2013 and compiled just 14 victories over that stretch.

Things got so bad that New York was left with no choice but to negotiate a buyout and cut ties. The end result for Rick, who hasn’t played a game in the NHL since the 2012/2013 campaign?

The Islanders send him an annual check for $1.5 million through 2029.

Carl Crawford – Boston Red Sox

  • Deal: 7 Years, $142 Million

In fairness to the Boston Red Sox, Carl Crawford was an excellent baseball player through the 2010 season. Carl was a .296 hitter for his career and was coming off a year in which he led the AL with 13 triples and stole 47 bases. When Theo Epstein decided to fork out $142 million on a seven-year deal heading into the 2011 MLB season, it didn’t seem so outlandish.

How could Theo and the rest of the BoSox front office brass have known that Crawford would fall off the map the very next year?

A .255 batting average and a dreadful K/BB ratio of 104:23 meant Carl had gone from an All-Star outfielder to a below-average hitter in less than 12 months. To make matters worse, Carl began the 2012 campaign on the 60-day disabled list after tearing the cartilage in his left wrist.

The former Tampa Bay Ray star wound up appearing in just 31 games for Boston that year, ultimately hitting the DL once again when he cited discomfort in his left elbow. Crawford was officially shut down on August 19th and went under the knife just four days later.

Apparently, the Red Sox had had enough and traded him to the LA Dodgers two days after the surgery.

In all, Carl Crawford played 80 games for Boston. His contributions amounted to a .260 BA and 23 steals, along with proclaiming to the media that the environment in Boston was toxic.

That about sums up what Carl Crawford did for Beantown after signing that ridiculous contract.

Albert Haynesworth – Washington Redskins

  • Deal: 7 Years, $100 Million

Was Daniel Snyder just that senseless, or should agent Chad Speck have been charged for robbery?

How and why the Redskins owner arrived at the conclusion that it was a smart decision to sign Albert Haynesworth to a 7-year/$100 million deal after the 2008 season ended is beyond me.

Sure, Albert was a Pro Bowler in 2007 and 2008, and perhaps he was a hot commodity during NFL free agency that offseason. But the often out-of-shape defensive tackle had lots of red flags and excess baggage that shouldn’t have been ignored.

In 2006, Albert was suspended for five games after stomping on Cowboys center Andre Gurode’s head twice, including once after his helmet had been knocked off. The injuries to Gurode’s head required 30 stitches, and to this day, it’s one of the cheapest shots you’ll ever witness on the field of play.

Despite that inexplicable behavior, the Redskins couldn’t wait to land Haynesworth heading into 2009. They even gave him $41 million guaranteed in order to lure him in. Unfortunately for Washington, they were a lot more excited than he was.

Albert didn’t take his career seriously whatsoever and skipped all the off-season workouts. All Albert did upon his arrival was complain about the defensive scheme and cause problems in the locker room. After recording just 4 sacks in 12 games, Haynesworth wasn’t even a starter going into the 2010 season.

By the time it got to December, the Redskins could no longer take it and placed Albert on the restricted list. Washington traded Albert Haynesworth to New England after the season for a 5th-round pick in a draft that was taking place in two years.

You can read stories about Albert being sued by a woman who claims he impregnated her and refused to offer any financial help. You’ll also see headlines of how Haynesworth threw a punch at another man during a road rage incident or how he pleaded guilty for charges related to being reckless on a boat.

What you won’t find is any evidence of him playing solid football once he signed with the Redskins.

I think it’s safe to say that after just 6.5 sacks and a total of 20 games for parts of two seasons, this contract didn’t work out too well for Washington.

Mike Hampton – Colorado Rockies

  • Deal: 8 years, $121 Million

When Mike Hampton signed an 8-year/$121 million contract with the Colorado Rockies in 2001, it was the richest contract in sports at the time — period. One would assume they were paying for a premium pitcher.

Unfortunately, as things would turn out, Mike was anything but a flamethrower for the next eight years in the Mile High City.

In 2001, Mike struck out just 122 batters in 203 innings, despicably walking 85 batters and amassing a 5.41 ERA. And if you think those numbers are bad for the wealthiest pitcher in baseball, wait until you see what Hampton did in 2002!

Mike Hampton 2002 Season Stats
Wins Losses ERA Innings Pitched Strikeouts Walks
7 15 6.15 178.2 74 91

I can’t think of any pitcher, even in the back end of a starting rotation, who walks more batters than they strike out. Regrettably, Mike was supposed to be the ace of the staff. As an alternative, he was dished in November of 2002 to the Florida Marlins, who quickly sent him packing to Atlanta.

Not only did Mike not produce for the Rockies, but thanks to the contract, he continued to pour salt in their wound.

Colorado continued to pay Mike until 2005, despite him leaving the team in 2002. And it gets uglier.

Mike earned $1.9 million per year, plus 3% interest, all the way from 2009 through 2018. Forget about leaving Denver in ’02 and retiring in 2010; Mike was getting paid handsomely 16 years after he last threw a baseball for the Rockies!

Gilbert Arenas – Washington Wizards/Orlando Magic

  • Deal: 6 Years, $111 Million

In 2007, Gilbert Arenas was coming off his second consecutive year in which he averaged more than 28 points per game. Washington was so delighted with his production that when the 2008 season ended, the Wizards decided to sign him to a six-year, $111 million deal.

This was a bit befuddling when you take into account that Gilbert played in just 13 games during the 2007/2008 season due to a significant knee injury. More complications with his knee forced him to sit out in all but two games the following year, once again stunting the growth of the Wizards franchise.

The 2009/2010 season wasn’t about injuries, but it was the time period in which it all came crashing down for Arenas. After playing in just 32 games, Gilbert was suspended for the rest of the year in early January for the “gun incident” involving teammate Javaris Crittenton.

Arenas began the 2010/2011 season still as a member of the Washington Wizards, although that ended abruptly just 24 games in. With a 6-18 record and their star player shooting under 40% from the field, it was time for a big change.

Gilbert was traded to the Orlando Magic for Rashard Lewis, formally terminating his time in the nation’s capital. As bad as this deal was for Washington, it was just as bad or worse for the Magic.

Gilbert was amnestied by Orlando when there was still a chunk of $62 million owed. This basically means the Magic paid $62 million for the 49 games in which he played, 47 of which he was a reserve player.

Arenas finished his NBA career playing in 17 games for the Memphis Grizzlies in 2012, but here’s the crazy part.

Orlando didn’t stop paying him until October 31st, 2016.

Bobby Bonilla – New York Mets

  • Deal: $1,192,248.20 per year from 2011 until 2035

Dennis Gilbert was an insurance-turned-sports agent who used his background in insurance to lock up one of the most talked-about deals in the history of professional sports.

Here’s the thing.

The New York Mets wanted to get rid of Bobby Bonilla in 2000 but were on the hook for owing him an additional $5.9 million. They could have paid the man his money and washed their hands clean of the situation.

But that’s not what ensued.

Somehow, someway, Gilbert was able to work his magic and manipulated the Mets into agreeing to defer the money for 11 years, with an annual interest rate of 8%.

For those of you who aren’t math majors, this means New York will end up paying Bobby $29.8 million until 2035 — even though Bonilla hasn’t played a game since 2001.

By being patient and trusting the process, Bobby is going to pocket an extra $24 million or so. Or think about it this way.

Some baseball players retire and are forced to find another gig. Other professional athletes call it quits and wind up in massive amounts of debt, eventually having to file for bankruptcy. What is Bobby Bonilla doing?

He’s resting on his laurels, waiting until July 1st arrives. That’s because every year from 2011 until 2035, he’ll open his mailbox on the first day of July and see a check for $1,193,248.20.

Going Away

It’s mind-boggling to think that some of these contracts actually existed. Having an agent who understands leverage can go a long way when structuring a deal, and these eight examples are the living proof.

It’s only a matter of time before we see another bizarre deal put in place. I promise you it won’t be long until we’re all talking about an enormous contract that doesn’t make sense.

After all, this is professional sports. There’s a whole lot of money flying around, and sometimes, it winds up in places that aren’t exactly justified.


The Worst Contracts Ever Signed in US Sports History

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The Worst Contracts Ever Signed in US Sports History


Sometimes in sports, individual players can get the last laugh. Here are eight examples of a professional sports team signing a horrendous long-term deal.


Michael Wynn

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