Free agency. It’s probably the most polarizing topic in the sports world. Fans call in to radio shows or comment on blog sites, complaining about contracts. Whether it’s the amount of money or the amount of years, there’s always a bone to pick.
To fans, the business of professional sports is personal. They feel as though teams and players are insulting their intelligence by signing these exorbitant deals. Their grievances are somewhat warranted. Over the past 20 years, many star players have signed big contracts that ended up being disastrous in retrospect.
Technically, this isn’t about being overpaid. It’s about being undeserving of the deal you signed, no matter the cause. Some players get injured, fail to produce as expected, or get caught up in off-the-field issues.
Is Mike Conley Jr. deserving of the $153 million deal he signed this past summer with the Grizzlies? That remains to be seen. Or how about Giancarlo Stanton’s $325 million deal with the Marlins? He is still young, and has enormous potential, so we don’t know just yet. A certain amount of time needs to pass before we judge whether a player truly earned the money he received.
With hindsight being 20/20, here are 20 athletes who didn’t deserve big contracts:
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20 Jake Peavy - Chicago White Sox
Jake Peavy was on top of the pitching world in 2007. He earned the National League “Triple Crown” in pitching, winning 19 games with a 2.54 ERA, and striking out 240 batters. He signed a four-year deal with San Diego that December, worth $52 million. It was the richest contract in team history. However, injuries began to derail Peavy’s career. An ankle injury in May 2009 put him on the DL, and things only got worse for him once he was traded to the Chicago White Sox in July.
He finished the 2009 season at a disappointing 9-6, and after a lukewarm first half of 2010, missed the remainder of the season with an arm injury. He finished the 2011 season with a mediocre 7-7 record and a 4.92 ERA, as injuries and fatigue limited him to just 18 total games.
He still earned a $16 million salary, equating to $168,421 per strikeout. The White Sox parted ways with Peavy via trade to the Red Sox in July 2013.
19 Matt Cassell - Kansas City Chiefs
Cassel took the football world by storm in 2008 when he replaced the injured Tom Brady as the New England Patriots’ starting quarterback. The Patriots wanted to capitalize on that success and used their 2008 franchise tag on Cassel and signed him for another season.
The Patriots traded Cassel to the Kansas City Chiefs the following February, and the quarterback signed a six-year, $62.7 million deal with the team that summer. Cassel struggled to a 4-11 record as a starter, throwing for 2,924 yards with 16 TDs and 16 interceptions. He rebounded well the following season as he threw for 27 TDs, and led the Chiefs to a division title.
However, in 2012, Cassel crumbled. He threw nine interceptions and committed five turnovers through the first five games of the season before being sidelined with a head injury.
The Chiefs demoted Cassel to backup before eventually releasing him in March 2013. Cassel has since bounced around the league between the Vikings, Cowboys, and Titans, never quite living up to that 2009 contract.
18 Carlos Boozer - Chicago Bulls
By the time the Bulls acquired Boozer in a 2010 sign-and-trade with the Jazz, the 29-year-old forward had already proved fragile. He came off a healthy 2009-10 season where he averaged 19.5 points and 11.2 rebounds per game, but underwent arthroscopic knee surgery just a year before.
That didn’t stop the Bulls from signing the German-born forward to a five-year, $75 million deal. He missed 23 games due to injury in his first season in Chicago, but rebounded the following year to average 15 points per game over 66 games. However, his postseason struggles in 2014 sealed his demise in Chicago. He averaged 9.6 points per game over five games and was released via amnesty clause that summer.
He spent one season in Los Angeles, but the Bulls were still forced to pay $13.5 million of his $16.8 million salary.
17 Jonathan Stewart - Carolina Panthers
It’s no secret that today’s NFL is quarterback-centric. The days of running backs like Barry Sanders, Emmitt Smith, and LaDainian Tomlinson racking up huge totals seem long gone.
Apparently the Carolina Panthers didn’t receive that memo when they signed running back Jonathan Stewart to a five-year, $37.8 million deal in 2012. At that point, the former 2008 first round pick showed signs of decline. He hadn’t rushed for 1,000 yards since 2009 (his only season with such totals) and split starting duties with DeAngelo Williams during the 2010 and 2011 seasons.
To make matters worse, Stewart suffered an ankle injury during the 2012 preseason, and struggled to stay healthy as he accumulated just 336 total yards that year. He played only six games during the 2013 season.
Thankfully, 2015 saw his best production since 2009, so perhaps Stewart is turning a corner. However, Stewart’s injury history is always a risk, and his $9.5 million cap hit should be reserved for the upper echelon of running backs, who can routinely top 1,000 yards and stay 100 percent healthy.
16 Jeremy Lin - Houston Rockets
Now, I’m not a huge Knicks fan, but I’d be lying if I said I wasn’t swept up in the “Linsanity” craze in early 2012. Jeremy Lin, an undrafted point guard out of Harvard, led a surprise turnaround for the Knicks that February. Lin averaged 22.5 points and 8.7 assists in 12 starts before the All-Star Break as the Knicks went 9-3.
Although “Linsanity” subsided later that season as his production returned from otherworldly levels, Lin still cashed in that summer. The San Francisco native signed a three-year, $25 million contract with the Houston Rockets. The first two years of Houston's offer paid Lin around $10 million total, and $14.8 million in the third year. That’s a bit much for a player who had one flash-in-the-pan run with the Knicks.
Fortunately for Houston, they wouldn’t foot that entire bill, as they traded Lin to Los Angeles after two seasons. Lin played one year in purple and gold, struggling in Byron Scott’s offense. He spent one season with the Charlotte Hornets before signing a three-year, $36 million deal with the Brooklyn Nets in 2016.
15 Scott Gomez - New York Rangers
Gomez is just one of many boneheaded free agent signings by Rangers GM Glen Sather. The fast-skating center was just one year removed from a 33-goal, 84-point season with the New Jersey Devils when he signed a lucrative contract with his club’s crosstown rivals.
Terms of the deal were $51.5 million over seven years, ridiculous for a player who only topped 80 points once. Gomez performed well in his first season in blue, registering 54 assists and 70 points, but his production declined the following year, to 42 assists and 58 points.
Sather thought Gomez could be a number one center, but the Anchorage, AK, native was anything but. Fortunately, in 2009, Sather found a suitor for Gomez’s albatross contract. He traded Gomez to the Montreal Canadiens in a packaged deal that included star defenseman and future Rangers’ captain, Ryan McDonagh.
That trade was arguably the best thing to come out of Gomez’s time in New York. He never registered a 60-point season again in his NHL career. He retired on August 31, 2016.
14 Mike Smith - Arizona Coyotes
When Mike Smith signed a six-year, $32 million extension with the Arizona Coyotes, many fans thought they would be getting the goaltender who led the ‘Yotes to the 2012 Western Conference Finals. Instead, they got a goaltender-turned-sieve who went 14-42 in 62 starts in 2013-14, allowing 187 goals against.
Smith rebounded to win 15 games the following season, but injuries limited him to just 32 games. So, at age 34, Smith has four years remaining on his deal at $5.6 million per year.
The Coyotes likely can’t trade him, given his age and unfavorable cap hit. They could cut ties with the netminder via buyout, or just keep him. If he continues his improved play (despite the injuries), perhaps this won’t be such a bitter pill for Arizona to swallow. One thing is for sure, though: With the strong play of youngster Louie Domingue, Smith isn’t even the best goalie on the Coyotes team.
13 Allan Houston - New York Knicks
At the time, one could argue Houston actually deserved the six-year, $100 max contract he signed with the Knicks in 2001. Just two years earlier, he hit the game-winning basket to send the eighth-seeded Knicks past the top-seeded Miami Heat in Game 5 of the 1999 Eastern Conference Quarterfinals, and had since become an All-Star and fan favorite. Yet, every fan and GM would revise that opinion if they foresaw Houston’s doomed career path post 2001.
Houston played well through the first two years of the deal, averaging roughly 21 points per game from 2001-2003.
Unfortunately, knee injuries quickly took their toll, causing him to miss 32 games in the 2003-04 season and 62 the season after.
Houston was forced in early retirement in 2005. He didn’t play a single game over the final two years of his deal. Yet, due to his guaranteed contract, he was still the second highest paid player in the league.
12 Wade Redden - New York Rangers
Another ill-advised Glen Sather signing. In fact, the puck-moving defenseman may be the worst free agent acquisition in team history. Redden came to New York on a six-year, $39 million deal after spending 11 productive years with the Ottawa Senators. Redden was consistent, both offensively and defensively, putting up 101 goals and 410 points in 838 games in Ottawa. Sather signed Redden to a six-year contract, worth $39 million.
From the very start, Redden struggled on the Blueshirts’ blueline. He scored a career-low 26 points in 81 games in his first season on Broadway. In 2009-10, his second season, Redden continued to regress, potting just two goals and 14 points. That’s 40 points for $16 million over the first two seasons. Disappointing would be an understatement.
Sather waived Redden the following season in a wise salary-cap move, and eventually bought out the remainder of his deal in 2012. Redden continued to receive compensation from the team through the 2014-15 season despite never playing another game in New York.
11 Carl Crawford - Boston Red Sox
It was tough to decide which Red Sox free agent signing was worse: Carl Crawford or Pablo Sandoval. Despite Sandoval’s underwhelming play and injury woes during his first two seasons in Boston, Crawford takes the cake as the worst signing in team history.
For one, Crawford only spent two years of his seven-year, $142 million deal with the Red Sox. His performance was hardly deserving of that money, and that’s being kind. He put up a meager .711 on-base percentage in 161 games over two seasons. He struggled to a .255 batting average during the 2011 season, while wrist injuries sidelined him for much of the 2012 season.
To make matters worse, the speed for which he was known for had all but disappeared during his tenure in Beantown. The Red Sox somehow found a way to dump Crawford in a trade to the Dodgers in August 2012. Crawford described the Red Sox team environment as “toxic,” yet he continued to struggle in L.A. The team released him in June of 2016.
10 Sam Bradford - St. Louis Rams
It’s been a while since the 2010 first-round pick won the NFL’s Offensive Rookie of the Year Award. Before that season, Bradford signed a six-year, $78 million contract. Since then, he has 78 career touchdown passes. The 28-year-old has never won more than seven games per season, yet he makes a million dollars per TD pass.
The only year he truly deserved that money was his first season in 2010. Bradford has struggled to stay healthy since, missing six games in 2011 with an ankle injury, and suffering a season-ending ACL tear in Week 7 of the 2012 season.
After missing the entire 2014 season with another ACL injury, he was traded to the Eagles. He threw for 19 TDs in his first and only season in Philadelphia. Despite signing a two-year, $36 million extension with the Eagles in 2016, Bradford was traded to the Minnesota Vikings on Sept. 3.
9 Bobby Holik - New York Rangers
I know I said the Wade Redden signing was the worst in Rangers history, but I may have to revise that claim. Bobby Holik’s five-year, $45 million contract is utterly atrocious in retrospect. Consider the fact that Holik, a longtime Devils center, had never scored more than 29 goals or 65 points in season, and was never paid more than $3.5 million per year. Why, then, would Glen Sather sign him to a deal which paid him an average of $9 million per season?!
It was hardly surprising that Holik’s production didn’t meet expectations. He scored just 16 goals and 35 points during the 2002-03 season, his first in a Rangers uniform. His cap hit was $9.6 million that season, equating to roughly $274,000 per point. Let that sink in.
He rebounded somewhat during the 2003-04 season, potting 25 goals and 56 points, but still, terrible numbers given his enormous salary. Sather wisely decided to buy out the remainder of Holik’s contract before the 2004-05 lockout.
8 JaMarcus Russell - Oakland Raiders
JaMarcus Russell, widely regarded as one of the biggest busts in NFL draft history, was selected first overall by the Oakland Raiders in 2007. He made things difficult from the start, holding out until he secured a six-year, $61 million deal with $32 million guaranteed.
The deal was a complete flop, as Russell went 7-18 in 25 games as a starter in Oakland. The team released him in May of 2010 after just three seasons. His stat line? An 18–23 touchdown-interception ratio, a 65.2 passer rating, and 15 lost fumbles. He completed just 52 percent of his passes.
Since leaving Oakland, Russell made a few fruitless comeback attempts. In 2016, he went so far as to write letters to all 32 NFL teams offering to play one year for free. Not one team responded.
7 Ryan Howard - Philadelphia Phillies
Ryan Howard electrified the baseball world at the start of his career, winning the 2004 NL Rookie of the Year Award. The 2006 NL MVP also won the Silver Slugger Award in 2009.
After a second straight World Series appearance in 2009, the Phillies rewarded Howard with a five-year, $125 million contract. He appeared deserving at first, hitting 30+ home runs in each of the first two years of the deal. Yet, from 2012 on, his production fell off a cliff. He began that season on the DL with an ankle injury, which limited him to just 14 home runs and 56 RBI in 71 games.
Things only got worse from there. He hit .266 with 11 home runs in 2013 before a season-ending knee injury in July. He struck out a league-leading 190 times in 2014. Howard hit a mere .229 as the league’s sixth highest paid player in 2015. For as great as Howard’s performance was before signing that huge contract, his days of $25 million-per-year production seem long gone.
6 Josh Hamilton - Los Angeles Angels/Texas Rangers
I applaud Hamilton for rejuvenating his career in the late 2000s after overcoming drug addiction. From hitting 35 home runs in the thrilling 2008 Home Run Derby, to winning the 2010 AL MVP, Hamilton’s comeback was heartwarming to say the least.
In each of his final three seasons in Texas, Hamilton averaged .313 with 33 home runs and 134 games played. It seemed fitting that the Angels signed the All-Star outfielder to a five-year, $125 million contract in 2013.
However, injury troubles and drug relapses plagued Hamilton during his time in Anaheim. He hit just 31 home runs in his two seasons with the team. He went 0-13 in the 2014 ALDS, and suffered a drug relapse during recovery from offseason shoulder surgery.
The Angels traded the troubled Hamilton back to Texas in April 2015, but were still obligated to pay him his $23 million salary. As of September 2016, Hamilton is a free agent.
5 Alexei Yashin - New York Islanders
The Islanders put out big time to acquire Yashin from the Senators on draft day in 2001. The only thing worse than the trade package New York offered (which included a young Zdeno Chara and a first round pick), was the ridiculous contract GM Mike Milbury signed Yashin to. The terms? Ten years, $87.5 million!
Yashin’s production immediately declined during his first season on Long Island. He went from 40 goals and 88 points in Ottawa to 32 goals and 75 points in New York; very solid production, but not worthy of nearly $9 million per year.
His totals declined every season until the lockout. After a mild resurgence in 2005-06, Yashin sputtered to 18 goals and 50 points in an injury-riddled 2006-07 season. The Islanders bought out the Russian winger that offseason, agreeing to pay him $2.2 million annually until 2015. The only deal worse than Yashin’s? See below.
4 Rick DiPietro - New York Islanders
Rick DiPietro’s contract with the Islanders may very well be the worst in NHL history. After a promising start to his career, the former number one overall pick signed a 15-year deal worth $67.5 million with the team in 2006. He won a respectable 58 games for the Islanders over the next two seasons.
However, his NHL fortunes took a 180-degree turn soon after, as a plethora of injuries limited him to just 54 games from 2008-2013. DiPietro chose to retire in 2013, once the Islanders bought out the remainder of his contract. The team agreed to pay him $1.5 million annually until 2029!!! Think about that. The length of the buyout payments supersedes the length of the original contract! Talk about a disaster.
Fortunately, DiPietro has since found success in radio, and hosts a daily sports talk show on ESPN 98.7 in New York.
3 Gilbert Arenas - Washington Wizards
Gilbert Arenas’ six-year, $111 million contract with the Wizards was arguably the least infamous move of his troubled career. He signed the deal in 2008 after playing just 13 games the previous season. He appeared in TWO total games the following season due to injuries.
He derailed a promising start to the 2009-10 season when he admitted to bringing unloaded firearms into the Wizards’ locker room that December. The NBA suspended Arenas the following January, and his career and image never recovered.
He was traded to Orlando in 2010, where he played one year before being waived in 2011. Save for a brief 17-game stint on the Grizzlies in 2012, Arenas hasn’t played in an NBA game since. Yet, he still received $22.3 million in 2014 as part of the final year of that ill-fated Wizards contract. Arenas, out of the league for two years, managed to be the third highest paid player that season.
2 Bobby Bonilla - New York Mets
The former Pittsburgh Pirate signed a five-year, $29 million deal with the Mets. However, the three-time Silver Slugger’s production declined during his two separate stints with the Mets (1993-1995, 1999) and he clashed repeatedly with management and team reporters. Bonilla even sat out of Game 6 of the 1999 NLCS against the Braves. The Mets finally released him at season’s end.
This is where things got crazy. The Mets still owed Bonilla $5.9 million, but they didn’t want to pay. Bonilla’s agent set up a deal where the Mets could defer payment until 2011, but had to pay eight percent annual interest.
Bonilla currently receives $1.19 million per year from 2011 to 2035 for a total of $29.8 million. So, the Mets’ 24-year pay period is six times as long as Bonilla’s four-year tenure with the team! Bonilla gets the last laugh, but perhaps no one is less deserving of that money. Well, there is one guy….
1 Alex Rodriguez - New York Yankees
Who else could it be? A-Rod was one of the most naturally gifted athletes in MLB history, and could’ve been a perennial All-Star and first ballot Hall of Famer even if he hadn’t taken steroids. He would certainly deserve the 10 year, $275 million deal with the Yankees if he was clean and honest.
It’s not just his PED use on the field, but his conduct surrounding PEDs off the field. It’s the fact that he lied multiple times about the issue, and threw Yankees’ team doctors under the bus after he was implicated in the Biogenesis scandal in 2013.
He even planned to sue the Commissioner and the MLB Players’ Union after he was handed a record 211-game suspension in 2014. Rodriguez dropped the lawsuit soon after, but was suspended the entire 2014 season.
His deteriorating performance during his finals years in pinstripes would be reason enough for not earning the richest contract in baseball history. More importantly, it’s the fact that he cheated, and LIED about it, that truly makes him undeserving of being the MLB’s highest paid player.
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