MLB’s Biggest Free-Agent Duds In The Past Decade

MLB’s Biggest Free-Agent Duds In The Past Decade

Baseball teams spend an enormous amount on player salaries. We saw that in spades this offseason with several stars signing monster multi-year contracts. However, not all free agent signings turn out as hoped. As evidenced below, once some free agents signed their long-term deals, their talents disappeared.  Time will tell if these new signings become another sad story to include with MLB’s biggest free-agent duds in the past decade. But who was the biggest swing and a miss in the last 10 years?

A Rivalry Renewed: Jacoby Ellsbury

Interdivisional rivalries can make baseball GMs do something they’ll pay for dearly in subsequent years. The most recent example of this abject failure is the New York Yankees signing Jacoby Ellsbury.

Ellsbury was two years removed from his random 32-home run season, but the leadoff hitter was still hitting around .300 while playing elite defense. The Yankees thought removing the centerfielder from the Boston lineup would help them as much as it would hurt the Red Sox. Unfortunately for the Bronx Bombers, Ellsbury only played four seasons of his seven-year, $153 million contract and was sub-par at best.

It’s a Midwest Thing: Jason Heyward

Another tragic case of a divisional rivalry followed by regret is the Chicago Cubs’ signing of Jason Heyward. Heyward never lived up to his potential as the game’s best prospect in Atlanta, leading the Braves to ship him off to St. Louis. During his time with the Cardinals, Heyward lacked power but was the best defensive right fielder in the game.

The Chicago Cubs, amid their championship window, needed to make a splash, which they did when they signed Heyward to an eight-year, $184 million contract. Heyward’s “motivational speech” led the Cubs to victory in Game 7 of the 2016 World Series. Because of this, Cubs fans tend to overlook his .700 OPS during his seven-year stay.

The Other Side of the Bay: Barry Zito

Although no one even uttered Barry Zito’s name in the cinematic version of Moneyball, he was the driving force—along with Tim Hudson and Mark Mulder— for the A’s success in the early 2000s. Zito wasn’t anywhere near the peak he hit when he won 23 games and the Cy Young award in 2002, but that didn’t stop the San Francisco Giants from forking over $126 million over seven years for the southpaw in December, 2006.

To say Zito struggled to fulfill his end of the contract would be an understatement, considering he went 63-80 with a 4.62 ERA with San Francisco. The good news for Zito is that despite his troubles, he earned two World Series rings in 2010 and 2012, respectively.

Three Strikes: Gary Matthews Jr., Josh Hamilton, & Albert Pujols

Instead of being the subject of Angels in the Outfield, maybe Gary Matthews Jr., Josh Hamilton, and Albert Pujols should have been in Back to the Future. Then, they could have stopped Curt Flood and Marvin Miller from making history for free agency in Major League Baseball. When Miller and Flood granted players free agency, they changed the game forever.

While these signings were more than 10 years ago, it seems as if the Angels sold their soul for their World Series win in 2002 since everything after that has been a nightmare, particularly regarding free agent spending with these three giant misses:

  • Gary Matthews Jr.: Five years, $50 million
  • Josh Hamilton: Five years, $125 million
  • Albert Pujols: 10 years, $240 million

Matthews Jr. played three below-average seasons with L.A. before finishing with the Mets. Hamilton struggled with off-the-field issues that hurt his two years with the Angels. And lastly, Pujols’s best year with the Angels was his worst year in St. Louis. Even landing superstar Shohei Ohtani cannot exorcise these demons.

Baseball feels like it’s the fickle sport regarding free agency, and MLB’s biggest free-agent duds in the past decade further prove that point.