MLB Legend Harold Reynolds Hints At Red Sox's $115 Million Dream Target

Does the longtime MLB analyst have the right idea?
Nov 1, 2023; Phoenix, Arizona, USA; Fox Sports analyst Harold Reynolds prior to the Texas Rangers game against the Arizona Diamondbacks during game five of the 2023 World Series at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
Nov 1, 2023; Phoenix, Arizona, USA; Fox Sports analyst Harold Reynolds prior to the Texas Rangers game against the Arizona Diamondbacks during game five of the 2023 World Series at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images / Mark J. Rebilas-Imagn Images
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The Boston Red Sox need starting pitching. But so do a lot of Major League Baseball teams.

The competition this winter is going to be fierce, but the Red Sox need to assert themselves. That starts with knowing who their top targets are, then being aggressive to make sure they come in at the top of the market when it comes to the offer stage.

Assuming the Red Sox are going to spend, it comes down to finding the right fit. Fenway Park can be a tricky place to pitch, and the American League East is generally a tough environment for pitchers too. Boston needs someone who can handle all that and stay locked in for a full 162 games.

Longtime baseball analyst and former two-time MLB All-Star Harold Reynolds knows a thing or two about fit, and he has a recommendation. In a recent segment on MLB Network, Reynolds paired the Red Sox with Los Angeles Dodgers star hurler Jack Flaherty, who is coming off his first career World Series ring.

"I'm looking at style of pitching. This isn't Jack Flaherty with the Cardinals anymore... He's throwing a lot more breaking pitches," Reynolds said. "I think Boston's on that track of loving the breaking pitch. They like the guys that throw that hook a lot more. And they have money."

Flaherty, 29, was one of the best strikeout pitchers in baseball this season, racking up 194 punchouts in 162 innings. He also compiled a 13-7 record and 3.17 ERA in 28 starts split between the Dodgers and Detroit Tigers.

Contract-wise, Flaherty's projections are tricky because he's coming fresh off signing a one-year, $14 million prove-it deal. MLB Trade Rumors recently projected that he would land a five-year, $115 million deal, which is the most optimistic prediction seen yet, but also appears feasible.

At some point this winter, the Red Sox have to land a big punch. That could be Flaherty if the organization sees the same fit Reynolds does.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org