Shin-Soo Choo and 10 Worst MLB Contracts of Last 10 Years

Jason Martinez@@mlbdepthchartsContributor IDecember 21, 2013

Shin-Soo Choo and 10 Worst MLB Contracts of Last 10 Years

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    The Rangers will pay Choo $130 million through his age 37 season.
    The Rangers will pay Choo $130 million through his age 37 season.Dustin Bradford/Getty Images

    Back in April, I ranked the 10 worst MLB free-agent signings of the past decade, with a focus on two recent signings—Albert Pujols and Josh Hamilton of the Los Angeles Angels—that were already in serious danger of joining them. 

    While Pujols and Hamilton each have plenty of time to rebound and ensure they won't crack any similar lists in the future, you can see how quickly a player can be hit with the "bust" label. Hamilton was only 20 games into his five-year, $125 million contract at the time of the article. 

    So what will Shin-Soo Choo—the newest $100 million man in the majors after agreeing to terms with the Texas Rangers on a seven-year, $130 million deal earlier Saturday, via Jon Heyman of CBS Sportsneed to do to avoid being lumped in with Alex Rodriguez and Chone Figgins and Barry Zito? 

    Too late. According to Dan Szymborski of ESPN, his ZiPS projections place Choo's deal as the third worst in MLB history at the time of the signing behind Rodriguez's second 10-year deal and Ryan Howard's current five-year, $125 million deal.  

    Looking at the 31-year-old Choo's "similar batters through (age) 30" comparison at Baseball-Reference.com, there isn't too much to get excited about if you're a Rangers fan hoping for a continued string of success throughout the course of his deal.

    Two of the closest comparisons are outfielders Bernard Gilkey, who spent the majority of his 12-year career with the St. Louis Cardinals, and Rusty Greer, who played all nine of his big league seasons with the Rangers. 

    Choo's 162-game average for ages 25-30 seasons (2009-13)
    BAOBPSLGOPSRH2B3BHRRBIBBKSBCS
    .290.392.469.86197176394218388146218

    *Via Baseball-Reference 

    Gilkey's 162-game average for ages 25-30 seasons (1993-97)
    BAOBPSLGOPSRH2B3BHRRBIBBKSBCS
    .289.362.464.826971723942087661011812

    *Via Baseball-Reference

    Greer's 162-game average for ages 25-30 seasons (1995-99)
    BAOBPSLGOPSRH2B3BHRRBIBBKSBCS
    .309.393.449.88310418539421101859063

    *Via Baseball-Reference 

    Eerily similar, right? The only difference is that neither was fortunate enough to land a payday anywhere close to Choo's, even by the standards of that era. If they had gotten big-money, long-term deals that took them past their mid-30s, there's a chance those contracts could've given Jason Bay and Gary Matthews Jr. a run for worst contracts of all time for a free-agent outfielder. 

    Gilkey's 162-game average after age 30 season (1998-2001)
    BAOBPSLGOPSRH2B3BHRRBIBBKSBCS
    .242.326.362.6894495211948478563

    *Via Baseball-Reference 

    Greer's 162-game average after age 30 season (2000-2002)
    BAOBPSLGOPSRH2B3BHRRBIBBKSBCS
    .290.362.438.800951815041283738253

    *Via Baseball-Reference 

    Not only was Gilkey unproductive, for the most part, throughout the remainder of his career, he also had a tough time staying healthy with an average of only 87 games per season. He made over $15 million over the course of his last four seasons in the majors. Choo will make close to $19 million in each of the next seven.

    While Greer continued to produce on the field, injuries limited him to only 73 games per season from age 31 until his retirement. Prior to the 2002 season, he was signed to a three-year, $21.8 million contract extension. He played in only 51 more games.

    But is it really fair for any system to label Choo a likely bust already? Using Rodriguez, Howard and Werth as a starting point, here's a look at some other seemingly risky investments and how they've turned out.

Alex Rodriguez: 10 Years, $275 Million

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    Scott Halleran/Getty Images

    Rodriguez opted out of a 10-year, $252 million deal after seven very productive seasons between the Rangers and Yankees, only to re-sign with New York for an even more lucrative $275 million contract.

    The second 10-year contract was off to a strong start, but ZiPS was right on the money. It's turned out to be one of the worst contracts in the history of sports. The return on the Yankees' investment could be about three very good years (.914 OPS, 32 HR, 109 RBI per season from 2008 to 2010) and some change.  

    At least they won a World Series title, in which he contributed positively, and could recuperate some of the money if his 211-game suspension is upheld.

Ryan Howard: 5 Years, $125 Million

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    Dustin Bradford/Getty Images

    When the Philadelphia Phillies decided to extend Howard through his age-36 season at a rate of $25 million per year, he was 30 years old with an NL MVP under his belt. He had a career .961 OPS, an average of 37 homers per season and he was set to become a free agent after two more seasons. 

    In retrospect, they should've just let him play out the remainder of his deal and become a free agent. In the first two seasons of his new deal, Howard has a .752 OPS with 25 homers and 194 strikeouts in 151 games.

    If he can't improve on that, this could turn out to be one of the worst investments of all time. Do baseball players get better at age 34 these days? 

Jayson Werth: 7 Years, $126 Million

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    Jennifer Stewart/Getty Images

    Jayson Werth didn't have his breakout season until age 28 with the Phillies, his fourth organization as a professional. So he was fortunate to get a seven-year deal when he was finally eligible for free agency after his age 31 season in 2010. 

    The Washington Nationals, who made the decision to pay him $18 million per year through his age 38 season, appeared to have made a huge free-agent blunder after Werth had an unproductive first season and then spent the majority of year two on the disabled list. 

    While he got back on track in year three, posting a .931 OPS in 129 games last season, the Nats will need Werth to be one of the rare players to fight off Father Time and continue to produce into his mid-to-late 30s if this investment is ever going to be viewed as a positive. 

Albert Pujols: 10 Years, $240 Million

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    Lisa Blumenfeld/Getty Images

    After a slow start in 2012 (.709 OPS through 39 games) and an injury-plagued 2013 season, Pujols is viewed as a player on the decline as he enters his age-34 season. 

    With eight years and over $200 million still remaining on Pujols' deal, the Angels appear to be "overpaying" a former star much earlier than had been expected when they signed him. Even five "typical Pujols" seasons and five of an aging player who becomes just "average" would've been acceptable.

    If Pujols doesn't bounce back in 2014 and maintain his production for a few more seasons, his contract could easily surpass Rodriguez's as one of the worst ever.

Vernon Wells: 7 Years, $126 Million

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    Harry How/Getty Images

    Vernon Wells was a superstar outfielder when he signed a lucrative contract extension to keep him in Toronto through his age-35 season.

    The Blue Jays didn't get quite the production they were hoping for in the first three years of his new deal, but Wells was far from a bust after posting a .793 OPS with 22 homers and 34 doubles per season.

    But in what may have been one of the best-timed trades in MLB history, the Jays traded Wells to the Los Angeles Angels before year four of the deal and only had to take on $5 million of the remaining amount, which was close to $90 million.

    Bad move.

    Wells had a .687 OPS in two seasons with the Halos before he was sent packing to the Yankees, along with most of his remaining salary, for two fringe minor leaguers.  

Barry Zito: 7 Years, $119 Million

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    Thearon W. Henderson/Getty Images

    From the get-go, Barry Zito failed to make a strong impression on his new fanbase. He allowed eight earned runs in six innings in his second start as a San Francisco Giant and never really recovered. 

    Over his seven-year career in San Francisco, Zito posted a 63-80 record with a 4.62 ERA. Not quite what the Giants had in mind when he had entered free agency with a career 102-63 record, 3.55 ERA, three All-Star appearances and a Cy Young award while with the Oakland A's. 

Johan Santana: 6 Years, $137.5 Million

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    Mike Stobe/Getty Images

    When giving up a handful of very good prospects in a trade for a player who is eligible for free agency after just one more season, signing that player to a contract extension can help to eliminate the potential of future regret. 

    In Johan Santana's case, the New York Mets added five additional years to Santana's contract after acquiring him from the Minnesota Twins prior to the 2008 season. Only two of those five were very good (24-18, 3.05 ERA from 2009-10). He missed two of the final three seasons while giving the Mets a 4.85 ERA in 21 starts in the season he was able to pitch. 

    During Santana's final season under contract in 2013, in which he missed recovering from a shoulder injury, one of the prospects the Mets traded away for Santana—Carlos Gomez of the Brewers—was busy posting an .843 OPS with 24 homers, 27 doubles, 10 triples, 40 stolen bases and winning a Gold Glove.  

Josh Hamilton: 5 Years, $125 Million

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    Thearon W. Henderson/Getty Images

    Not only was Hamilton's history of drug and alcohol addiction a reason for concern for interested teams as he entered free agency, he was already entering his age-32 season and had struggled mightily during the end of his last season as a Texas Ranger.

    The Angels were willing to take a chance, however, and they're probably regretting the decision after year one of his contract. It took a relatively strong finish (.910 OPS, 4 HR in 37 games) to boost his overall OPS over .700 and to push him over the 20-homer mark.

    In his five years with the division rival Rangers, Hamilton posted a .912 OPS with 28 homers per season. He had a career-high 43 in 2012 in three fewer games (148) than he had in his first with the Halos.  

Adam Dunn: 4 Years, $56 Million

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    Rick Osentoski-USA TODAY Sports

    Adam Dunn had a career .902 OPS and an average of 35 homers in 10 seasons when he entered free agency prior to the 2011 season. Still, the Chicago White Sox were taking a risk when they gave the strikeout-prone slugger $56 million for his ages 31-34 seasons. 

    It didn't take long to realize their mistake as Dunn posted an atrocious .569 OPS with only 11 homers in 122 games during his first season in Chicago. He bounced back in 2012 with his sixth career 40-homer season (41), but his .800 OPS was the second lowest of his career. Until 2013, that is, when he had a .762 OPS. 

Brian Roberts: 4 Years, $40 Million

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    Patrick Smith/Getty Images

    Still under contract for one more season, Brian Roberts inked a four-year contract extension with the Orioles that would keep him in Baltimore through his age-35 season in 2013. We can say that the O's should've waited, but he went out and hit 56 doubles and stole 30 bases the season before his new deal kicked in. 

    If not the O's, some team would've given him at least $10 million per season. And it would've been a huge mistake. Roberts proved to be one of the most injury-prone players in the game, playing in only 192 games over the course of the four-year contract while posting a .669 OPS.