Pirates rumors: Ben Cherington will get help from familiar trade partner to ruin Paul Skenes' prime

The Toronto Blue Jays are here to make Paul Skenes’ life more miserable.
Pittsburgh Pirates pitcher Paul Skenes during the 2025 All-Star Game
Pittsburgh Pirates pitcher Paul Skenes during the 2025 All-Star Game | Dale Zanine-Imagn Images

Unfortunately for two-time All-Star pitcher Paul Skenes, he’s likely stuck with the Pittsburgh Pirates even if he wanted a trade ahead of the July 31 deadline.

Things stand to get far worse for Skenes. It’s bad enough that they’ve wasted his first two seasons, entering Wednesday at 41-61 and 14 ½ back in the NL Wild Card race. The Pirates are all but assured of their ninth losing season in 10 years despite Skenes’ sparkling 1.91 ERA and stellar 5.3 bWAR.

However, for all of their current issues, the Pirates have several tradable assets who should expect to wear new uniforms next week. Infielder Isiah Kiner-Falefa, reliever Dennis Santana, and third baseman Ke’Bryan Hayes have all heard their names mentioned in trade reports and proposals as the deadline nears.

Pittsburgh can afford to part ways with Kiner-Falefa or veteran slugger Tommy Pham. Any hopes of the Pirates planning to contend in 2026 will likely end with a potential Mitch Keller trade — and the Toronto Blue Jays are reportedly ready to go all out and snag Keller amid a heated AL East race. 

Keller threw six innings of three-run ball and earned his fourth victory of the year on Tuesday night. The 29-year-old owns a 3.53 ERA and a 97-30 K-BB ratio in 125 innings.

Paul Skenes should be livid if the Toronto Blue Jays trade for Mitch Keller

Keller signed a five-year, $77 million extension with the Pirates in February 2024, less than three months before Skenes made his long-awaited debut. Barely a year later, Keller has an excellent opportunity to possibly escape the Pirates.

The Pittsburgh Post-Gazette reported that the Blue Jays have entered the race for Keller’s services; the Post-Gazette previously named the Cubs, Mets, and Yankees as potential suitors. The Post-Gazette noted that the Pirates and Blue Jays have made several trades in recent years, including the move that brought Kiner-Falefa to Pittsburgh last July. 

Keller makes plenty of sense for a Blue Jays team with a three-game lead over the Yankees in the AL East. Only 6 ½ games separate the first-place Blue Jays and fourth-place Rays with just over a week before the deadline.

Then, you have the Pirates, who are in yet another rebuild that has no imminent signs of ending. Pittsburgh has scored two or fewer runs in 10 of Skenes’ 21 starts, which is why he’s only 5-8 and could become the first starting pitcher to win the Cy Young with a losing record.

The Pirates insist that they won’t trade Skenes, and he hasn’t publicly requested freedom — our apologies, we mean a trade — just yet. Let’s see if that changes come the offseason, and if Skenes can somehow reunite with Keller somewhere outside of Pittsburgh.

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