Josh Winckowski Offers Starter Upside

Image credit: Boston Red Sox

Though Josh Winckowski was off the baseball map with the absence of a minor league season in 2020, the 22-year-old righthander’s performance at instructional league last fall was sufficiently impressive to convince two teams to trade for him.

A Blue Jays 15th-round pick out of Estero (Fla.) High in 2016, Winckowski topped out at High-A in five seasons in the Toronto organization. 

But when the 22-year-old reported to instructional league last fall, his velocity had jumped from the low 90s to sit regularly in the mid and upper 90s.

On top of Winckowski’s potentially plus fastball, evaluators saw a solid slider and a hard changeup that represented a potential third pitch. The 6-foot-4 202-pound righty possessed a big league arm with starter upside.

That profile made him an attractive trade chip. The Blue Jays dealt him to the Mets as part of the package that landed Steven Matz.

The Mets subsequently sent Winckowski to the Red Sox in the three-team deal that shipped Andrew Benintendi to the Royals, outfielder Khalil Lee to the Mets, and Winckowski, Franchy Cordero and three additional players to be named to the Red Sox.

“There are a lot of different ways his career can go,” Red Sox chief baseball officer Chaim Bloom said. “He’s not a finished product yet. But he has a really good chance to impact the major league staff in some capacity.”

Winckowski’s initial showing this year at Double-A Portland further seemed to validate that impression.

He regularly sat 94-96 mph with at least a solid-average slider, and his changeup had shown promise. In five starts to open the year, he had a 1.33 ERA in 27 innings with 8.7 strikeouts and 3.0 walks per nine innings.

His changeup—which is sometimes described as a splitter—still needs to improve for Winckowski to stick as a starter. But his first impression in the new organization has been positive.



— Righthander Thad Ward was placed on Double-A Portland’s injured list in May with a forearm strain.

— Outfielder Tyler Dearden needed just 14 games to set a new career high for homers with five at High-A Greenville.

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