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With baseball’s Winter Meetings about to start, here are some pros and cons of pitchers the Red Sox may target

The Red Sox have wanted their starters to go deep into games, and Blake Snell proved again this year he can do that, earning his second Cy Young Award.Gregory Bull/Associated Press

Baseball’s Winter Meetings are set to begin Monday in Nashville and maybe that’s when the hot stove will finally heat up.

In recent years, there have been some big signings. Gerrit Cole and Stephen Strasburg signed hefty deals during the 2019 meetings. After two years in which the meetings weren’t held because of COVID-19 and then the lockout, Aaron Judge and Trea Turner landed deals worth $360 million and $300 million, respectively, at the 2022 meetings.

The Red Sox landed Masataka Yoshida for five years at $90 million last year, but this year the Sox have put an emphasis on pitching.


Here are some pros and cons of some potential Red Sox targets:

Blake Snell

Pros: Snell just won his second Cy Young Award after registering a 2.25 ERA in 32 starts for the Padres. He’s a strikeout machine (234 in 180 innings), something the Red Sox lacked last season. The team has wanted its starters to go deep into games, and Snell proved again this year he can do that, going five or more innings in 29 starts. In 20 of Snell’s starts, he went at least six.

Cons: There aren’t many. Snell can be prone to the walk, which was an issue for the Red Sox in 2023. He surrendered 99 walks and 5.8 hits per nine innings (both of which led the majors), but his career 11.1 strikeouts per nine innings helps quell some of his “weaknesses.”

Yoshinobu Yamamoto

Pros: The Red Sox are one of the strong suitors for Yamamoto. If they do, indeed, land the star starter by way of Nippon Professional Baseball, he would be reunited with former teammate Yoshida. While it’s not mandatory that Yamamota plays alongside a familiar player, it’s certainly a plus.

Yamamoto, 25, is one of the highly coveted free agents in this class. He posted a 1.21 ERA in 184 innings for the Orix Buffaloes in 2023. The Red Sox have familiarity with Japanese pitchers, namely Daisuke Matsuzaka and Koji Uehara, which would help in the transition phase.


Cons: The MLB schedule will always be a question mark. Japan is the size of California, and Yoshida, for example, struggled this past season with the 162-game schedule (and travel) compared with 144 games in NPB. But Yamamoto’s adjustment might not be as difficult because he’s not a position player, and will instead be called upon every five days.

And if there are any questions regarding the adjustment to the majors from an on-field perspective, the Mets’ Kodai Senga, another former teammate of Yamamoto’s, put together an impressive first year in the big leagues.

Jordan Montgomery

Pros: Montgomery knows what it’s like to pitch in a big market, spending his first five-plus seasons with the Yankees, the team that drafted him. Montgomery is also a consistent starter, carrying a career 3.68 ERA. When he was traded to the Cardinals in 2022, St. Louis harped on Montgomery challenging hitters more with his fastball, a pitch the Yankees discouraged.

Montgomery put together his best season in 2023 between the Cardinals and Rangers, with a 3.42 ERA and a World Series title. Montgomery is just entering his age-31 season, a perfect age for a free agent starter.

Cons: The Sox need a top-of-the-line starter, and it’s fair to question whether Montgomery can carry that load. He’s not a huge strikeout guy but is good enough, at 22.5 percent for his career. His 43.4 percent ground-ball rate would work well at Fenway, but considering how bad the Sox’ defense was this past season, is that really a plus?


Marcus Stroman

Pros: Stroman knows how to pitch. And for a team that needs just that, he could be a good fit for the Sox. Stroman has made at least 25 starts each of the last three seasons, with a 3.45 ERA in that time. He’s another pitcher who doesn’t rely heavily on the strikeout and needs his defense behind him. Nevertheless, he can cause an offense fits, often inducing weak contact because of his full arsenal of pitches.

Cons: Stroman can be a nuisance in the clubhouse, according to a source. He can also be difficult with the media. Those cons alone might not be worth the pros.

Marcus Stroman has made at least 25 starts each of the last three seasons, with a 3.45 ERA in that time. Kevin C. Cox/Getty

Lucas Giolito

Pros: When he’s on, Giolito might be one of the better shows in baseball.

Cons: He has a career ERA of 4.43, including 4.88 between three teams in 2023. The biggest question with Giolito is, who are you getting? And for a top-tier starter, that might not be a question you want to ask yourself.

Shohei Ohtani

The Red Sox are reportedly out of contention for Ohtani, which is the only con.

Julian McWilliams can be reached at julian.mcwilliams@globe.com. Follow him @byJulianMack.