4 worst free agent fails of the Red Sox's 2023-24 offseason

The Red Sox passed on a lot of talented free agents this offseason, but these four top the list.

Feb 19, 2024; Glendale, AZ, USA; Los Angeles Dodgers left fielder Teoscar Hernandez (37) during a spring training workout in Glendale, Arizona
Feb 19, 2024; Glendale, AZ, USA; Los Angeles Dodgers left fielder Teoscar Hernandez (37) during a spring training workout in Glendale, Arizona / Jayne Kamin-Oncea-USA TODAY Sports
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The tale of the offseason for the Red Sox hasn't been who they've brought in, but who they couldn't bring in. Liam Hendriks, Lucas Giolito, and Cooper Criswell have been the additions in free agency, but the biggest headlines have come from Boston's whiffs.

Sure, the Sox added some players through trades. Tyler O'Neill is sure to bring some power to the lineup and play solid defense. Greg Weissert, who has earned praise this spring, was one of the pitchers the Red Sox acquired for sending Alex Verdugo to the Yankees. But the players the Sox didn't get would have made the biggest difference in the lineup.

Whoever in the front office is responsible for the inaction on the free agency front doesn't matter in this situation. Ultimately, these players could've been Red Sox right now but aren't, and pointing fingers won't change that.

More players passed up on the Red Sox in free agency for a slew of reasons, but these four players are the worst whiffs of the winter.

4 worst free agent fails of the Red Sox's 2023-24 offseason

Teoscar Hernández

The Red Sox were looking for a right-handed power bat after Adam Duvall and Justin Turner departed in free agency. They thought they found their man in outfielder Teoscar Hernández, fresh off his third straight season of 20+ home runs. He posted 26 long balls for the Seattle Mariners in 2023.

The match was perfect, as both the Red Sox and Hernández expressed interest in getting a deal done. Hernández also loves playing at Fenway Park, as he has 14 home runs and 44 RBI in 46 games at Fenway, including three multi-homer games and a six RBI game in 2021.

However, the Red Sox fumbled the negotiations. Hernández said that the Red Sox were one of the two finalists to sign him this offseason but they refused to offer him more than two years. Hernández said he wanted more out of an offer from Boston, but it didn't budge from their two-year offer.

Ultimately, Hernández signed with the other finalist, the Los Angeles Dodgers, on a one-year deal worth $23.5 million. The case of Hernández, who wanted to play in Boston, is just another example of what could have been for the Red Sox.

Jorge Soler

After Hernández signed with the Dodgers, the target for teams like the Red Sox in need of a power bat turned to Jorge Soler. He led the Marlins in home runs in 2023 with 36, with no other Marlins hitter reaching 20 home runs.

Soler isn't as good a defender as Hernandez is, but he makes up for it with his slugging skills. His fit in Boston would have been a middle-of-the-order masher who would likely rotate position-wise between DH and left field.

Unfortunately for the Red Sox, they couldn't get a deal done with Soler either. The San Francisco Giants, also looking for more thump in their lineup, swooped in and signed Soler for three years at $42 million. While San Francisco is a pitcher's ballpark, he's still a much-needed addition for them, though his production would unquestionably be much better in hitter-friendly Fenway Park in a Red Sox uniform.

Yoshinobu Yamamoto

Right after Shohei Ohtani, the next-best free agent on the market at the start of the offseason was Yoshinobu Yamamoto. The 25-year-old made the jump to the majors from Japan after seven successful seasons in Nippon Professional Baseball.

It was easy to see why teams were lining up to get Yamamoto, as his electric pitches and tantalizing talent made him the best rotation option available. All the big market teams were making pitches to him, the Red Sox included.

Yamamoto ended up joining Ohtani in Dodger Blue as he signed for 12 years at $325 million, instantly creating a super team in Los Angeles. Not long after, it was revealed that both the New York Mets and Yankees each offered Yamamoto at least $300 million, with the Mets offering him the same contract he signed with the Dodgers.

While a recent report from Bob Nightengale indicated that the Red Sox also offered Yamamoto at least $300 million, ownership has been quiet about the negotiations with Yamamoto, not willing to disclose what was or wasn't offered. The lack of clarity on the situation makes it hard to believe they hit $300 million, and if they had tried harder, perhaps they could have landed the Japanese star.

Shōta Imanaga

The next-best Japanese pitcher available on the market was Shōta Imanaga, who has pitched eight impressive seasons in Japan and was the starting pitcher for the World Baseball Classic championship game against Team USA.

With the time running out on his posting window, Imanaga signed a unique four-year, $53 million contract with the Chicago Cubs, securing his jump to the majors at age 30.

The Red Sox were very much in the running to secure Imanaga's services. According to Alex Speier of the Boston Globe, the Red Sox had offered Imanaga a two-year contract with two additional vesting years, not far off from what he ended up signing for with the Cubs.

All offseason, the Red Sox have been unwilling to offer long-term contracts to players to the frustration of the fanbase. A four-year deal for Imanaga isn't a huge commitment, and at the money he signed for, the Red Sox shouldn't be let off the hook for not matching that offer to try and land the southpaw, especially with all the candidates for rotation spots right now being right-handed.

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