Kuzul

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 Sports—need 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. 

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. 

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.

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