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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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.