10 biggest busts in the history of MLB free agency

Roger Clemens
Roger Clemens' second stint with the Yankees didn't end as the Bronx Bombers hoped. Photo from Bronx Pinstripes.

When compiling a list of the biggest MLB free agent busts it is safe to say that a writer is spoiled for choice. Free agency in the league came about in the aftermath of the 1972 Flood vs Kuhn Supreme Court case. Free agent opportunities then became even greater in 1976 after the reserve clause in the league was destroyed in an arbitration case. The new collective bargaining agreement in the fallout of that decision opened the market for players and deals have flowed ever since.

The problem with baseball free agency in terms of bad contracts is that the players have the power. The lack of a salary cap means that bidding wars begin and escalate quickly.

That leads to some of the worst MLB contracts ever and players become among the biggest free agency busts when they are paid way more than they are actually worth.

Biggest MLB free agent busts

It is in the offseason where most of the player movement in baseball occurs. Every player wants the tag of the biggest contract at his position and the player arms race only ever seems to get more intense.

The reasons for the worst free agent contracts in MLB history vary. Promising starts can be ruined by injury or a player could just be ineffective out of the gate. Here are 10 of the biggest MLB free agent busts.

Mo Vaughn, Angels

The problem with bigger players is that age tends to catch up with them in a hurry. This is something that teams have learned over the years, but in 1999 sluggers were all the rage and the Angels overpaid for one.

Mo Vaughn signed a six-year, $80 million deal and was crushing it with 30-plus home runs each year for the first two years. An injury led to Vaughn missing his third year and he came back massively overweight and out of shape. Vaughn was traded to the Mets when he had a less than productive season before retiring due to knee problems.

Danny Tartabull, Phillies

By some metrics the one-year, $2.3 million deal that the Philadelphia Philles gave right fielder Danny Tartabull in 1997 is the worst free agent deal of all time.


While it was not a big money contract by any means, Tartabull still managed to underperform at his new club to an epic degree. Tartabull had seen decent production in Kansas City in the late 80s. By this point however, he was done. He appeared in just three game for the Phillies during his one year stay and seeing as he didn’t get a single hit he was basically paid for doing nothing.

Denny Neagle, Rockies

A five-year, $51 million deal for a pitcher in Colorado is not the best piece of business (though there is worse to come on this list).

The reason that the Denny Neagle deal was so bad is how it ended, along with the lack of production to that point. Neagle was never able to show his best form in Denver with his first three years seeing him amass a 5.57 ERA.

His fourth year was lost to injury and then at the end of that season, he was charged with soliciting a prostitute and had his contract canceled through a morals clause. He would never play in the Majors again.

Roger Clemens, Yankees

The number here is just eye opening. In 2007 the New York Yankees paid an aging Roger Clemens $28 million for one last hurrah in Gotham. It is hard to say what sort of record would justify a contract paying $4.7 million per month if all marks were hit, with Clemens making just over $1 million per start.

His 6-6 record in the regular season with a 4.18 ERA didn’t justify the money thrown at Clemens. Nor did the hamstring injury that saw Clemens leave Game 3 of the ALDS that year, a series the Yankees lost to the Cleveland Indians.

Read more: MLB free agency explained

Jason Bay, Mets

Jason Bay had starred for the Boston Red Sox and when he hit the free agent market at the end of the 2009 season the outfielder has plenty of suitors.

The New York Mets signed Bay to one of the worst MLB contracts ever, giving him $66 million over four years.

Bay played the game with a style that saw him become more prone to injury as he got older. He hit .259 and six homers in his concussion shortened first-season with the Mets. This was a year after hitting 36 homers for the Red Sox. His contract was terminated a year early due to a pile of injuries and lack of production.

Rusney Castillo, Red Sox

It is always a gamble giving an unproven international player a monster deal. The Boston Red Sox found this out the hard way when giving Rusney Castillo $72.5 million over seven years in the middle of the 2014 season.

Castillo simply wasn’t as major league ready as scouts thought when they had seen brief snippets of his play.

The length of the deal was done to give Castillo time to adjust. He never made the adjustment, however, and quickly became the best paid minor leaguer in the game. That huge deal saw Castillo play less than 100 games over the span of three seasons, batting .262 with seven homers.

Melvin Upton Jr, Braves

This deal didn’t make much sense at the time and in hindsight, it just seems much, much worse.

Melvin (BJ) Upton signed a five-year, $72.5 million contract with a Braves squad looking for hitting, speed, and defense. The problem is that Upton had batted an anaemic .242 in his previous four seasons.

He was also a strikeout machine (in a bad way) having struck out more times than just three other players in the entire league over that span. He hit just .198 for the Braves over two years before they cut their losses, having to package Upton with All-Star closer Craig Kimbrel to get a deal done.

Jason Schmidt, Dodgers

Jason Schmidt looked like the missing piece for the Los Angeles Dodgers pitching rotation when he signed a three-year deal for $47 million prior to the 2007 season.

The three-time All-Star with the San Francisco Giants saw his career wrecked by injury, however, and as a result, this is one of the worst free agent contracts in MLB history. Schmidt played just 10 games over the length of his deal because of injuries to his pitching arm. He won just three games. The nature of fully guaranteed MLB contracts means that the Dodgers paid Schmidt over $15 million per win.

Read more: Biggest draft busts in MLB history

Mike Hampton, Rockies

You could kind of see this one coming. Mike Hampton was a breaking ball heavy pitcher with a career 3.44 ERA. The Colorado Rockies needed pitching help, so they gave the lefty $121 million over eight years.

The air in Colorado, however, is different. Fastball pitchers survive. Breaking ball pitchers, generally, do not. Hampton pitched two of his eight seasons in Denver putting up a 5.75 ERA in 62 starts before a mercy trade involving the Marlins and Braves took him out of town.

Josh Hamilton, Angels

It is the size of this contract that makes this one of the worst MLB contracts ever.

Josh Hamilton signed for the Los Angeles Angels on a five-year deal worth $125 million. He lasted two years with the organization, batting .250 in 2013 with 21 homers and .263 in 2014 with 10 home runs.

He also went hitless in the ALDS against the Royals where he was 0-for-13 at the plate. After a relapse in his drug addiction issues that offseason, the Angels traded Hamilton back to the division rival Texas Rangers. The California team had to essentially pay Hamilton’s contract for their rivals to take him off their hands.

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