Boston Red Sox: Biggest free agent busts in franchise history

BOSTON, MA - APRIL 15: Pablo Sandoval #48 of the Boston Red Sox runs to the dugout during the third inning against the Tampa Bay Rays at Fenway Park on April 15, 2017 in Boston, Massachusetts. All players are wearing #42 in honor of Jackie Robinson Day.(Photo by Maddie Meyer/Getty Images)
BOSTON, MA - APRIL 15: Pablo Sandoval #48 of the Boston Red Sox runs to the dugout during the third inning against the Tampa Bay Rays at Fenway Park on April 15, 2017 in Boston, Massachusetts. All players are wearing #42 in honor of Jackie Robinson Day.(Photo by Maddie Meyer/Getty Images) /
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TORONTO, ONTARIO – JULY 2: David Price #10 of the Boston Red Sox pitches against the Toronto Blue Jays in the first inning during a MLB game at the Rogers Centre on July 2, 2019 in Toronto, Canada. (Photo by Mark Blinch/Getty Images)
TORONTO, ONTARIO – JULY 2: David Price #10 of the Boston Red Sox pitches against the Toronto Blue Jays in the first inning during a MLB game at the Rogers Centre on July 2, 2019 in Toronto, Canada. (Photo by Mark Blinch/Getty Images) /

David Price

I’ll probably take a lot of grief for this one, but the Red Sox signing of David Price was one of their worst ever. Like Lackey, he ended up helping the team win a World Series, but it was never fun along the way and most fans and media members didn’t mourn the loss when he was traded to the Dodgers in February 2020.

Price was well-known to the Red Sox from spending the first six and a half seasons of his career in Tampa. He was a thorn in Boston’s side pitching for their division rival and he was arguably the reason the Red Sox didn’t return to the World Series in 2008, his pitching in game seven of the ALCS being an early career highlight.

By the time the Red Sox inked him to a seven-year, $217 million deal in the winter of 2015 (at the time the richest free-agent contract for a pitcher in history), Price was established as one of the top pitchers in the game, albeit one who couldn’t seem to get it done in the postseason.

It’s not that Price was bad in his four seasons in Boston, it’s just that he wasn’t great. The Red Sox seemed to go against their self-imposed edict of not paying for a pitcher’s decline years when they signed Price at the age of thirty. He started off his Red Sox tenure strong when he went 17-9 in 2016, but 2017 was not a good season for the team or Price.

He battled a wrist ailment in 2017 that seemed to be correlated to his excessive video game playing and he drew the ire of fans, former players, and the media for his very public and foolish feud with Dennis Eckersley (it was a one-sided feud at that since Eck refused to rise to the bait Price kept putting forth).

Price was awful in the 2016 and 2017 postseasons, continuing his terrible career track record in October by going 0-1 with a 6.75 ERA over the two years. He rebounded in 2018 by going 16-7 in the regular season and finally exorcising his postseason demons that October. After losing his start against the Yankees in the ALDS, Price caught fire.

He went 1-0 with a 3.38 ERA in his two starts against the Astros in the ALCS and then went 2-0 with a 1.98 ERA in his two World Series starts against the Dodgers including winning the deciding fifth game. Many fans (myself included) believed Price should have won the World Series MVP award over Steve Pearce.

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After the season Price announced he wasn’t going to opt-out and would remain in Boston. He was actually one of the Red Sox’s most consistent pitchers in an otherwise forgettable 2019 season, going 7-5 while struggling with a wrist issue before finally being shut down for the season in September.

In an effort to offload salary and reset the luxury tax penalties, the Red Sox included Price in the Mookie Betts deal and sent him to Los Angeles in February 2020. Even so, the Sox will have to eat half of his remaining salary ($48 million) over the next three years. When all is said and done, was Price really one of the worst Red Sox free-agent signings ever?

He belongs on the list because even though he was very good for two seasons, great in one postseason, and vital to their winning the 2018 World Series, on the whole, the Red Sox didn’t get their money’s worth. They got two very good seasons, two injury-shortened seasons, and a lot of headaches. While Price was well-liked by his teammates, he was not at all liked by Red Sox fans or the Boston media.

A lot of was due to the Boston media being brutal, but he did himself no favors with antagonizing a beloved figure like Eck (and unbelievably bringing it back up again in 2019), stating that he held “all the cards” after winning in 2018 (which many took to him not winning graciously and rubbing it in the media’s face), and what many perceived to be his incredibly thin skin.

All-decade 1960's Red Sox team. dark. Next

Like Lackey, ultimately Price helped the Red Sox win a World Series and for that reason alone should be considered a success, but in neither case did the team really get their money’s worth. This one will probably be debated by Red Sox fans for years to come, but for now, he belongs on this list.