The Pirates may be staring at one of those awkward front-office moments where the past comes back wearing a different uniform.
A November 4 Sportsnet piece from Blue Jays insider Arden Zwelling put Pittsburgh right-hander Carmen Mlodzinski on Toronto’s radar, and the names floated as possible returns included Addison Barger and Charles McAdoo. For Pirates fans, McAdoo is the one that jumps off the page. Pittsburgh drafted him in the 13th round in 2023, then shipped him to Toronto at the 2024 trade deadline for Isiah Kiner-Falefa.
That deal already has a complicated look to it. When the Pirates made the move in July 2024, they were trying to push toward a postseason run, and McAdoo was the cost of that gamble.
At the time, the 22-year-old was in the middle of a strong minor league season, batting .315 with 14 home runs and a .932 OPS across High-A Greensboro and Double-A Altoona. Ben Cherington decided the chance to add an established big leaguer was worth giving up a promising young bat.
The payoff never came. Pittsburgh missed the postseason in 2024, and Kiner-Falefa stayed with the club through most of 2025 before the Pirates put him on waivers in August. Toronto claimed him, which meant the Blue Jays wound up with both sides of the original swap: the prospect Pittsburgh gave up and the veteran it had acquired.
McAdoo’s development since then makes the idea of a reunion a little more than just a strange footnote. In 2026, he reached the majors with Toronto and hit .258 with three home runs in 97 at-bats. He also put together a solid year at Triple-A Buffalo, where he hit .269/.366/.465 with 16 home runs and 57 RBI in 89 games.
He still hasn’t proven himself as a major league hitter, but the appeal is obvious. McAdoo brings right-handed power and the kind of positional flexibility that could help a Pirates team with real uncertainty in the infield. Brandon Lowe could leave in free agency, and third base remains unsettled.
The catch is that Pittsburgh would have to pay for him again.
Mlodzinski is no throw-in. The 27-year-old posted a 3.95 ERA over 123 innings in 2026 and showed he can cover both starting and bulk relief roles. He has said he prefers to work as a traditional starter, though the Pirates’ rotation picture already includes Paul Skenes, Jared Jones, Bubba Chandler and Braxton Ashcraft, which leaves his long-term fit a little murky.
That makes him a logical trade chip if Pittsburgh wants to chase offense. But it also means the Pirates could end up moving a controllable major league pitcher just to bring back a player they once developed and dealt away.
If McAdoo has become a real big league option, the Pirates can’t ignore that just because they already gave him up once. Still, the optics would be hard to miss. Pittsburgh spent McAdoo on short-term help that didn’t lead to a playoff berth, and now Cherington could be weighing another trade involving the same player as the club tries to build off its first winning season since 2018.
With a potential December 1 lockout looming over the offseason, the Pirates may need to use their pitching depth to fix the offense. If that path leads back to McAdoo, it would be another reminder of how one deadline decision can keep circling back.
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