Former top Pirates prospect is helping fuel Blue Jays’ unlikely playoff push

The Toronto Blue Jays and Pittsburgh Pirates woke up Friday in remarkably similar places — at least if you only looked at their records.

Both teams are 59-64. The difference is that Toronto, despite sitting last in the American League East, is only two games out of the final AL Wild Card spot. Pittsburgh, meanwhile, is six games back in the National League and watching a once-promising season rapidly slip away.

And one of the players suddenly helping Toronto believe it can take advantage of a weak American League should be very familiar to Pirates fans. Charles McAdoo is back in the majors, and he's forcing the Blue Jays to keep writing his name into the lineup.

McAdoo's solo homer off Sonny Gray on Monday helped Toronto to a 2-1 win over Boston. It was his second major league home run and his fifth consecutive game with a homer when including the tear he was on at Triple-A Buffalo before being recalled.

For Pirates fans, watching this should come with some uncomfortable memories. Pittsburgh selected McAdoo in the 13th round of the 2023 MLB Draft, and he quickly became one of the better finds in the organization. By the middle of the 2024 season, he had surged into the Pirates' prospect rankings while hitting .315/.394/.538 with 14 homers and 17 stolen bases across High-A Greensboro and Double-A Altoona. Baseball America ranked him as Pittsburgh's No. 12 prospect at the time.

Then came the 2024 trade deadline. The Pirates were actually trying to win. They sat 55-53 shortly after the deadline and were firmly involved in the NL Wild Card race. Ben Cherington attempted to address an underwhelming offense by acquiring Bryan De La Cruz from the Miami Marlins and Isiah Kiner-Falefa from Toronto.

The price for Kiner-Falefa was McAdoo. At the time, it was at least understandable. Kiner-Falefa was having the best offensive season of his career, batting .292/.338/.420 with seven homers for Toronto, and his defensive versatility filled an immediate need for a Pirates team trying to reach the postseason.

The problem is that the move produced virtually no payoff. Kiner-Falefa hit just .240/.265/.322 in 50 games after joining Pittsburgh in 2024 as the Pirates' playoff push collapsed. He returned in 2025 and was a perfectly serviceable player, but hardly someone who justified surrendering a legitimate offensive prospect.

Less than 13 months after acquiring him, the Pirates placed Kiner-Falefa on waivers. Naturally, Toronto reclaimed him for their eventual pennant-winning run.

Former Pirates prospect Charles McAdoo is helping Blue Jays sneak back into playoff race as Pittsburgh stumbles

So Toronto ultimately got McAdoo and got Kiner-Falefa back. That's a tough transaction tree for Pittsburgh to defend.

It would be easier to stomach if the Pirates had gotten a postseason appearance out of the deal, but hey didn't. They finished 76-86 in 2024, went 71-91 in 2025 and now find themselves 58-63 in a 2026 season that was explicitly supposed to end their decade-long playoff drought.

McAdoo isn't suddenly a superstar, and it would be revisionist to pretend the Pirates traded away a can't-miss prospect. His development hasn't been linear. He struggled after joining Toronto's Double-A affiliate in 2024, posted a .732 OPS there in 2025 and has questions defensively. Even MLB Pipeline's current scouting report describes power as the carrying tool that will determine his ceiling. But that's almost beside the point.

The Pirates traded years of team control over an intriguing young hitter for an immediate upgrade because they believed they were ready to contend. Two years later, they're still waiting to contend. And the young hitter they gave away is suddenly providing exactly what the Blue Jays desperately need as they try to turn a disappointing season into an improbable playoff appearance.

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