How Red Sox stole Garrett Whitlock when Yankees ‘risk’ backfired


Many in the Yankees organization would not have been surprised if Garrett Whitlock developed into a standout major league pitcher, one who could be trusted in a win-or-go-home situation.

They just imagined he would be wearing pinstripes for that situation.

Instead, Whitlock could be a difference-maker in Tuesday’s wild-card game at Fenway Park, where the Red Sox’s best relief pitcher will remind the Yankees of what could have been.

Whitlock traded sides of the rivalry in December, when the Yankees left the righty pitching prospect exposed to the Rule 5 draft, in which the Red Sox made him the No. 4 pick.

It is uncommon for a Rule 5 selection to last — clubs shield top minor leaguers from exposure, and those picked cannot be optioned and must survive on the major league roster all season — yet, Whitlock was a rare case.

He was a promising arm rising through the Yankees’ system until Tommy John surgery in 2019 halted his ascent while at Double-A Trenton. The 2020 minor league season was wiped away, and Whitlock never pitched at the Yankees’ alternate site. They did not add him to the roster this offseason.

How Red Sox stole Garrett Whitlock when Yankees ‘risk’ backfired
Garrett Whitlock has become a weapon for the Red Sox after they selected him from the Yankees in the Rule 5 Draft.
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“There’s a lot of risks with pretty much every decision that teams make,” said Pat Osborn, who managed Whitlock at Class-A Tampa and Trenton. “This was probably one of the difficult ones for the Yankees. Maybe there was a hope that because he was injured, he would slip through the cracks. But these teams are smart, and the Red Sox did a heck of a job of scouting.”

Converting the minor league starter into a reliever allowed an easier way for Whitlock to stick, and he made the Red Sox’s roster out of spring training. In 46 games since, he has been one of the most valuable relievers in baseball in stints as long as 3 ¹/₃ innings. The 25-year-old posted a 1.96 ERA — the eighth-best in MLB among qualified relievers and better than any Yankee — and represents a weapon Boston is thrilled to have back.

Whitlock’s scoreless inning Sunday was his first outing in two weeks as he missed time with a right pectoral strain.

Through his 73 ¹/₃ innings this season, Whitlock and his mid-90s sinker has shown the upside the Yankees hoped they would see firsthand.

What stood out about the 18th-round pick in 2017 was his “incredible strike-throwing ability,” Osborn, who is now the minor league field coordinator for the Marlins, said on a Monday phone call. “Right away you noticed that.

How Red Sox stole Garrett Whitlock when Yankees ‘risk’ backfired
Garrett Whitlock has become a weapon for the Red Sox after they selected him from the Yankees in the Rule 5 Draft.
Getty Images

“He worked really fast, which I think caused some discomfort for hitters. And then his demeanor on the mound — you hear the description of pitchers as ‘bulldogs’ on the mound, and I think Garrett fits into that category.”

The Yankees liked Whitlock, whom MLB Pipeline ranked as their No. 27 prospect before his ’19 injury, and Trevor Stephan, another righty who was taken by Cleveland in the Rule 5 draft and stuck with the Indians through an up-and-down season.

But the Yankees were more comfortable keeping pitching options such as Albert Abreu, Brooks Kriske and Michael King while protecting further-down prospects in infielder Oswald Peraza, righty Alexander Vizcaino (since dealt to the Cubs), Roansy Contreras (since dealt to the Pirates) and righty Yoendrys Gomez.

“I told people that if he didn’t get hurt in 2019 and have to have that surgery, I don’t think this [emergence] would have been a surprise,” Osborn said of Whitlock. “I really think that he was on his way to becoming one of the Yankees’ better young pitching prospects.”

Instead, he is one of the Yankees’ bigger concerns in the faceoff with the Red Sox.