Red Sox Prospect Outlook: Josh Winckowski To Debut One Year After Trade?

Winckowski was one of five prospects brought to Boston in exchange for Andrew Benintendi


Mar 30, 2022

Before the start of the 2022 season, is evaluating several noteworthy prospects in the Boston Red Sox organization, using insight and analysis from industry experts to gauge each player’s outlook for the upcoming campaign. Next up: Josh Winckowski.

In Josh Winckowski, the Boston Red Sox got a promising right-handed pitcher as part of a five-player package for Andrew Benintendi.

Here’s everything you need to know about Winckowski, a 23-year-old who could make an impact for the Red Sox in 2022.

Winckowski’s story
Winckowski was drafted in the 15th round of the 2016 Major League Baseball Draft, and had to work his way up the minor league ladder without the pedigree of many of his teammates.

Since being drafted, Winckowski has learned the business of being a professional athlete the hard way, being traded twice in 2021 before the season even started.

First, he was shipped from the Toronto Blue Jays to the New York Mets in a trade centered around Steven Matz, then as part of the aforementioned Benintendi trade.

Last season, Winckowski started in Double-A Portland and worked his way up to Triple-A Worcester, where he found success. He’ll likely start the season where he left off in 2021.

Winckowski is the Red Sox’s No. 14 prospect, according to MLB Pipeline.

Scouting report
At 6-foot-4, 202 pounds, Winckowski has used his frame to develop elite velocity, especially out of the bullpen.

“In the Arizona Fall League, he pitched out of the bullpen and he was up to 98-99 mph, with a power breaking ball and then a changeup that looks kind of like a sinker because it’s thrown at like 90 mph,” Ian Cundall, director of scouting for, told last week.

Most-likely outcomeMulti-inning reliever.

Winckowski has started 72 of his 77 appearances at the minor league level. But he appears to be better suited for the bullpen.

“He’s a very interesting guy,” Cundall said. “I think he’s a reliever long-term, but I think his stuff is actually pretty interesting there.”

Winckowski appears to be a guy who could stick as a starter but will lose some electricity the longer he goes in outings.

“I think he could be someone who could get up in that multi-inning role, and I think he definitely has potential there,” Cundall said. “I’m not sure he’s a starter, and there’s nothing wrong with that. It’s a misconception that if you’re not a starter, it’s a failure. And that’s definitely not the case.

“Garrett Whitlock (is a) great example of what someone can do when they’re in the bullpen, and I think the long-relief role is what Winckowski is going to be best suited for. Because his stuff definitely tailed off when I saw him as a starter last year. But I think he definitely could be pretty good in that role, especially with his stuff ticking up out of the bullpen like it did in the (Arizona Fall League).”

Best-case scenarioLate-inning reliever/back-end starter.

Winckowski has the tools to be a future setup man at the big league level. His velocity puts him in a position for success in that role.

If he or the Red Sox are convinced that starting is the best path, he still could be a fourth or fifth starter. He’s not going to see the lineup three times very often, but that’s how the game is trending regardless.

SoxProspects ranking: No. 13

Winckowski has the velocity and secondary pitches to eventually become a productive member of the big league club. His ranking reflects as much, but he doesn’t quite have the ceiling that Brayan Bello (No. 6) and other elite prospects have.

Fenway forecast
It would be somewhat surprising if Winckowski does not make the Red Sox roster at some point in the 2022 season. His biggest hurdle will be to define his role comparatively to other depth options.

The Red Sox have a few prospects in a similar position as the big right-hander, including Kutter Crawford (No. 27) and Connor Seabold (No. 11), both of whom are also on the fringe of starting and relieving.

“I think Winckowski has more upside in the bullpen than Crawford does, but I think Crawford’s floor is probably a little higher because he’s got a better command profile and he’s a little safer than Winckowski,” Cundall said.

Seabold, Crawford and Winckowski will be able to provide depth to the Red Sox pitching staff in whatever role necessary, and all could see time in Boston this season.

Thumbnail photo via Andrew West/The News-Press via USA TODAY Sports Images
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