Worst MLB Free Agent Signings of All Time

Aside from winning the World Series or beating a sworn rival, I'm not sure anything in baseball is as exciting as free agency. This is especially true when there is a lot of talent on the market, and you're unsure if your team will make a big move or not. It keeps you alert and on the edge of your seat the entire offseason. As soon as you hear your team signed one of those stars, you're excited, for like a minute.

Then, you start to wonder if everything might go wrong. It's not an irrational fear; countless all-stars and highly sought after players have bottomed out after signing a big money free agency deal. This has resulted in some of the worst MLB free agent signings in history and continues to give fans apprehension every offseason. Not even Bryce Harper and his rumored $400 million deal are safe from the worrying aspect of free agency. The culprits for all of this anxiety and fear from fans, general managers, and anyone invested in baseball are as follows.

Josh Hamilton was the feel-good story of the MLB during his time with the Texas Rangers. Overcoming constant battles with drug addiction, which saw him suspended from the league for about two years (2004–2006), Hamilton hit 150 home runs with the Rangers, with 43 in 2012. He won the AL MVP in 2010 with a stat line consisting of a .359 batting average, 32 home runs, and 100 RBI.

The left-handed slugger signed a five-year contract worth $125 million with the Los Angeles Angels, but his substance issues became an issue again. He also did not have the same success on the field, as his OPS dropped almost 200 points in his first season. The Angels released him before the 2015 season and the Rangers signed him back. Interestingly enough, Hamilton signed for the league minimum with Texas while the Angels paid him significantly more just to get him off their team.

As the worst MLB free agent signings go, this one was truly out of left field (pun definitely intended). Jason Bay's career was as consistent as you could get. He consistently was in the neighborhood of a .300 batting average, 30 home runs, and 100 runs batted in for about seven seasons. Then, the New York Mets sign him to a $66 million deal over four years and it was not a pretty sight after that.

In his three seasons with the Mets, Bay hit 26 home runs, ten fewer than the 36 he hit with Boston the year before signing in Flushing. The Mets decided to end the four-year contract a season early and Bay would play one more season with the Seattle Mariners before hanging up his cleats.

The Colorado Rockies signed pitcher Mike Hampton to an eight-year, $121 million contract in the 2000 offseason. Hampton would play in two seasons in the Rocky Mountains before moving on, which is not ideal. He went 21–28 in his two years with Colorado, sporting a 5.75 ERA. Whenever your contract is over $100 million and you put up numbers like that, it's not a surprise when you're considered one of the worst MLB free agent signings ever.

While not eclipsing the $100 million mark like Hamilton and Hampton before him, Chan Ho Park is undoubtedly one of the worst MLB free agent signings of all time. After going 84-58 with the Los Angeles Dodgers, Park was able to turn his success into dollars. The Texas Rangers signed the pitcher for $65 million. The five-year pact went south quickly. The Rangers got 22 wins and 23 losses out of Park, whose ERA jumped from an average of 3.77 to 5.79 in three seasons. He also got into a strange, jump-kick fight shown above, not his finest moment.

The Los Angeles Angels are lucky they signed Shohei Ohtani, who has a bright future on the mound, because they have not had the best of luck with free agents before him. Gary Matthews Jr. had a career year in 2006 with the Texas Rangers, posting a .313 batting average, 19 home runs, and 79 RBI. Matthews Jr. was able to turn that one successful season into a five-year $50 million contract with the Angels.

He would not hit over .252 in his three seasons with the Angels and only produced 30 home runs in that time. His playing in Los Angeles came to an end at the conclusion of his third season. The center fielder would go on and play one more season with the New York Mets before retiring.

Despite having one of the best nicknames in baseball and all the success he had with the San Francisco Giants, "The Kung Fu Panda" could not figure out the east coast. After signing with the Boston Red Sox for $95 million over five years, Pablo Sandoval couldn't deliver.

The 2012 World Series MVP and three-time champion only suited up in red and gray for 162 games over three seasons. He hit 14 home runs, 59 RBI, and had a .237 batting average. The Red Sox released him in 2017 and he went to sign back with the Giants, where he has not had much success, which provides a small consolation victory for the Sox.

The Angels may mess up with batters, but it seems it's the Rockies who don't know what to look for in pitchers. After winning the World Series with the New York Yankees, Denny Neagle signed with the Rockies for five years and $51 million. He went 19–23 and averaged a 5.57 ERA. Oh, and he was charged with soliciting a prostitute, which forced the Rockies to take action against the right-hander. One of the easier choices to include in the worst MLB free agent signings, it's hard to tell if Neagle's off the field issues were worse than his issues on the field.

The Boston Red Sox free agent misery continues. Carl Crawford was an electric player for the Tampa Bay Rays. He had speed (leading the league in stolen bases four times), hitting ability (.296 career average), and just enough power (104 home runs in nine years). The dynamic outfielder signed with Boston, and much like Sandoval, forgot what baseball was.

Unfortunately for the Red Sox, this deal was bigger. Much bigger. Crawford signed a seven-year deal for $142 million to play in Beantown. All of his numbers declined sharply, with a lot of categories being the lowest since his rookie year. His stint would only last a season and a half before being moved. Tough luck for Red Sox fans, but at least they still have one of the most beautiful ballparks in baseball.

With the money at their disposal, and their desire to land the most coveted free agents, it makes sense for the New York Yankees to be responsible for some of the worst MLB free agent signings. Perhaps their biggest mistake was Carl Pavano. Coming off his first all-star year, Pavano inked a four-year $40 million deal with the Yanks. Injuries forced Pavano to miss a lot of time, starting only 26 times in three seasons. He finished with a respectable 9–8 record in pinstripes, but a less impressive earned runs average of five.

We arrive at the curious case of Melvin Upton Jr. Unlike some of the other worst MLB free agent signings before him, Upton found some success after his rough patch. In 2012, the Atlanta Braves signed Upton to a five-year deal for $72 million. Known more for his power than contact ability, Upton was supposed to bring a pop to the Braves' lineup. Sadly, that was not the case.

The outfielder hit for a .184 batting average in his first season in Atlanta with only nine home runs. He followed that up with a career-high number of strikeouts and a .208 batting average the next season. The San Diego Padres traded for Upton and he found some success there, with 21 home runs and a .257 average over a season and a half.