Winckowski’s Road to Recovery and Return: A Look at His Career Journey

In December, Winckowski underwent internal brace surgery, a procedure that is set to give him a chance to return to the mound later in the 2026 season. The surgery, which was reported by Adams, has a direct impact on the pitcher’s future, as the two-year contract he signed with the Toronto Blue Jays provides him with additional time. If the team decides to delay his return, he will have the option to make his comeback in 2027.

This surgery marks a significant chapter in Winckowski’s career. After several seasons with ups and downs, it appears that he is now focused on a successful return. His dedication to making a full recovery signals his determination to return to the role he once held as a starting pitcher, a position he held in 21 of his 121 MLB appearances with the Boston Red Sox between 2022 and 2025.

Through these seasons, Winckowski, a right-handed pitcher, has shown that he can be a reliable presence on the mound. Despite facing adversity with injuries, his career record stands at 13-14 with a 4.20 ERA. These numbers, while not necessarily spectacular, speak to his resilience and ability to contribute in various pitching roles, even when things are not going his way.

His journey to the major leagues started with the Blue Jays, who originally drafted Winckowski out of Estero High School in Florida in the 15th round of the 2016 MLB Draft. At that time, it was clear that the Blue Jays saw something special in him, even though he was a high school pitcher. His potential was undeniable, but what lay ahead was a long and winding road.

In January 2021, Winckowski’s future took a significant turn when he was traded to the New York Mets. Along with pitchers Sean Reid-Foley and Yennsy Diaz, he became part of the trade package that would see him head to the Mets’ organization. However, his time with the Mets was short-lived, as he never threw a single pitch for them.

Trade to the Red Sox and Rapid Development

In a swift move the following month, February 2021, the Mets sent Winckowski to the Boston Red Sox in a four-team trade. The deal was part of a larger exchange that included sending Andrew Benintendi to the Kansas City Royals. As part of the trade, Winckowski was accompanied by minor league outfielder Freddy Valdez, who would also join the Red Sox.

Winckowski’s transition to the Red Sox proved to be a pivotal moment in his career. He had been given a new home, and with it, the chance to prove himself. The 2021 season was a turning point in his development as he made his major league debut with the Red Sox. That year, as a rookie, he posted a 5-7 record with a 5.89 ERA. While the numbers weren’t ideal, they were reflective of the typical growing pains of a first-year pitcher. Despite the struggles, Winckowski showed flashes of potential, striking out 44 batters while walking 27 in 70.1 innings.

In 2023, Winckowski’s development took a more positive trajectory. He made the bulk of his 60 appearances out of the Red Sox bullpen, solidifying his place in the team’s pitching rotation. This transition to a reliever role seemed to benefit him, and he finished the season with a 4-4 record and a 2.88 ERA. His ability to strike out nearly a batter per inning (82 strikeouts in 84.1 innings) was a significant improvement, and it showed that Winckowski was becoming a more effective weapon in Boston’s bullpen.

His performance in 2023 was a testament to his work ethic and adaptability, proving that he could thrive in a variety of pitching roles. Notably, he made six appearances out of the bullpen in April, a time when the Red Sox were looking to establish a solid pitching lineup. However, Winckowski’s journey wasn’t without setbacks, as he was optioned to the minor leagues and made five appearances for Triple-A Worcester, starting three games.

The Road to Recovery: What’s Next for Winckowski?

In May, Winckowski’s commitment to his craft was evident. In his final appearance of the season on May 11, he threw 3.1 shutout innings for Worcester. This performance gave fans and analysts alike a glimpse into the pitcher’s potential, especially considering the challenges he had faced throughout the year. His resilience and ability to step up when needed were clear in this performance.

Now, with the Blue Jays looking toward 2026 and beyond, Winckowski’s journey is far from over. His internal brace surgery is a setback, but it also represents a fresh opportunity for him to prove that he can be a key part of the Blue Jays’ pitching staff when he returns. While there is still uncertainty about exactly when he will be able to make his return, the contract extension he signed with the Blue Jays gives him the extra time he needs to recover fully.

The question on everyone’s mind is whether Winckowski will be able to reclaim his role as a starting pitcher once he is healthy again. This is a decision that will ultimately be up to the Blue Jays and how they view his recovery. If he can return to form, there is no doubt that he could be an asset to the team’s pitching rotation. His experience as a starter, combined with his improved bullpen performances, suggests that he has the tools to succeed in both roles.

Could Winckowski Become a Key Contributor for the Blue Jays?

The Blue Jays, who have been focusing on building a strong roster for the future, will need all the help they can get on the mound. As the team continues to build its pitching depth, Winckowski’s potential return to form could be a game-changer for the Blue Jays in the coming seasons. The team is looking to contend for championships, and having a reliable arm like Winckowski could give them the depth and versatility they need to stay competitive in the AL East.

In the world of baseball, injuries are inevitable, but the road to recovery is just as important as the career milestones that come before. For Winckowski, his journey is a reminder of the power of persistence. He has overcome adversity and shown that he has the ability to adapt, whether as a starter or a reliever. His resilience is something that will serve him well as he works his way back from surgery.

For now, Blue Jays fans can only wait and see how this recovery process unfolds. But with Winckowski’s work ethic, dedication, and potential, the best is yet to come. Will he return to the mound and make an impact for the Blue Jays? It’s a question that fans will be eager to find out in the coming years.

As the 2026 season approaches, all eyes will be on Winckowski as he looks to prove that he can overcome this latest hurdle and become a key figure in the Blue Jays’ pitching staff.

Only time will tell, but one thing is for sure – Winckowski is not going down without a fight.