Red Sox Offseason Preview: Five Free Agent Pitchers Boston Could Target

Boston must find a way to improve its rotation

by Mike Cole

Oct 14, 2020

The Boston Red Sox have a very clear top priority this winter: improve the starting pitching.

Due to injury, illness and ineffectiveness, Red Sox starters had some of the worst numbers across the board in the pandemic-shortened 2020 season that ended up being one of the worst campaigns in franchise history.

There’s hope for the future, though. Just by getting pitchers like Chris Sale and Eduardo Rodriguez back healthy, the rotation should improve, and further development from someone like Tanner Houck is encouraging.

However, the Red Sox should also be looking outside the organization for improvements. The trade market could be more robust this winter than years past, as financial restraints stemming from the pandemic and lost gates could tempt teams to trade pitchers under contract.

For the sake of this exercise, though, we’re pinpointing a handful of free agent starters who will hit the market this winter that the Red Sox might want to target.

Trevor Bauer, RHP
There’s no better pitcher on the market than Bauer, the presumptive National League Cy Young Award winner. The hard-throwing right-hander picked a good time for the best season of his career, and he’ll look to cash in this winter. He’s made it no secret he’s open to sign just about anywhere, but here’s the potential hold-up for a team like the Red Sox. If Boston really wants to make a push for Bauer, it has to be sure it’s ready to contend in 2021, as the pitcher has often stated his desire to sign one-year contracts every year upon reaching free agency. Signing Bauer feels like a long shot, but the Red Sox definitely should at least look into the possibility.

Drew Smyly, LHP
Did Smyly unlock something this year in San Francisco? His 126 ERA+ and 2.01 FIP would be career bests if he kept them up for an entire season, but the thing that really jumps off the page is the 14.4 strikeouts per nine innings. That’s quite a jump from his career rate of 8.8 entering the 2020 campaign. He’s mostly a two-pitch pitcher at this point, with a fastball that averaged just under 94 mph (a career-high) and a curveball that he threw more than a third of the time in 2020. That certainly fits the recent Red Sox profile.

Jose Quintana, LHP
Hard to believe it’s been more than three years since the Cubs parted with pieces like Dylan Cease and Eloy Jimenez in order to land the left-handed Quintana from the crosstown White Sox. The Cubs won a World Series, which makes it easier to stomach the fact Quintana never quite ascended to the top of the rotation on the North Side. That’s not to say he wasn’t effective, though, making 78 starts for the Cubbies. A freak injury limited Quintana to just 10 innings in 2020, but he did strike out 12 in those 10 frames, a reminder he still has pretty good stuff. The soon-to-be 32-year-old could be a very attractive option for teams unwilling or unable to land a bigger fish like Bauer, Marcus Stroman or Kevin Gausman.

Matt Shoemaker, RHP
We’re taking a bit of a chance here with the 34-year-old right-hander. Shoemaker had a fine enough season, allowing 15 earned runs in 28 2/3 innings, but a 5.95 FIP indicates he might have been a little lucky. At the right price, however, the hope would be he’d regain the form he showed at times over various points of his career. In the six seasons entering 2020, Shoemaker had a 3.85 career ERA while striking out eight batters per nine innings — solid numbers. Here’s the catch, though: He’s only made 97 starts in those six seasons and just 12 starts combined in 2018 and 2019. For the right price, he’d be a worthwhile gamble.

Jon Lester, LHP
This suggestion is at least somewhat narrative-based. It would be pretty neat for Lester to return to Boston to finish his career. That’s not to say, however, he wouldn’t provide any value. As a back-of-the-rotation arm, you could do worse than a playoff-tested southpaw who hasn’t logged fewer than 170 innings in a full season since 2008. The 2020 season was the worst of his career, and he turns 37 in January, so you have to know what you’re getting. But again, for the right price as a back-end veteran, it’s an intriguing option. Lester himself sounds open to the idea, too.

Thumbnail photo via Jon Durr/USA TODAY Sports Images
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