Free Agent Signing: Blue Jays Sign Pitcher Who Held 'Grudge' Against Them

The Toronto Blue Jays are bringing in a pitcher who has admitted that he held a grudge against the team for trading him a few years after they drafted him. Right-hander Josh Winckowski was originally drafted by the Jays in the 2016 MLB Draft, but he was dealt away in 2021.

It must all be water under the bridge by now, as Winckowski has signed a two-year minor league deal with the Jays, after he was DFA'd by Boston a month ago.

Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the #BlueJays. Had internal brace surgery earlier this month. Hoping to pitch late in 2026. Plan right now is to build him back up as a starter when he’s healthy.
— Steve Adams (@Adams_Steve) December 31, 2025

Winckowski had elbow surgery in early December, an internal brace procedure. So at best, he could be ready late in the 2026 season. Reports have Toronto eyeing him as a potential starter once he gets healthy.

Back in 2023, while with the Red Sox, Winckowski explained the 'grudge' he still held against the Jays:

"I've always been a big chip-on-my-shoulder guy and sometimes I do the 'fake fire' stuff, so I still hold a grudge against them, to this day, even though it's probably not warranted," Winckowski told MassLive's Chris Cotillo. "I just fake it. Anytime I play them, I just want to do extremely well. Even just giving up a hit to them drives me crazy."

The 27-year-old became a versatile reliever with the Red Sox, while also throwing in a few starts here and there. He features a strong fastball and slider. Across 242 innings over 121 games, 21 of them starts, he had a 4.20 ERA in parts of four seasons, before a flexor strain in May sidelined him for the rest of the 2025 season.

He started his big league career in the rotation, then moved to the bullpen in 2023, where he threw 84.1 strong innings across 60 appearances, with a 2.88 ERA.

It's another depth move for the Blue Jays' pitching staff, in an offseason that's already added a few headliners, including Dylan Cease (7 years, $210M), Cody Ponce (3 years, $30M) and Tyler Rogers for the bullpen (3 years, $37M).