Latest trade deadline rumors hint Pirates positioned to empower Yankees' rival

Jun 5, 2024; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Jun 5, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

Recently, the Yankees were connected as a team "picking up steam" in the Mitch Keller sweepstakes. Noah Hiles of the Pittsburgh Post-Gazette followed up that report with a new one, labeling New York's rival as a new team involved in Keller's market. The Toronto Blue Jays are now reportedly showing interest in Keller, along with Isiah Kiner-Falefa, the utility guy they dealt to Pittsburgh last year.

Kiner-Falefa also has received rumored interest from the Yankees ahead of the deadline. If history repeats itself, Ben Cherington may be more inclined to deal to the Blue Jays' organization. His history of trading with the Yankees has not always gone swimmingly, and a handful of Cherington's free agents and trade acquisitions have a history with his former organization, Toronto. Last summer, in fact, he and the Jays linked up for the initial IKF trade.

Although it may be a mistake to trade Keller after all, it is great that there is a market forming over Kiner-Falefa, a veteran on an expiring deal that Pittsburgh needs to move on from. The Pirates will likely be after players similar to Cam Devanney, the prospect acquired in the Adam Frazier deal. The Yankees and Jays are the only two teams that have reported interest in Kiner-Falefa thus far, so the possible returns could feature Jesus Rodriguez from the Yankees (MLB Pipeline No. 30) or Yohendrick Pinango from the Blue Jays (MLB Pipeline No. 23). Both are having great years in the upper minor leagues and could be solid additions, especially for a rental.

The Pirates and Blue Jays are rumored to be be connected over Isiah Kiner-Falefa and Mitch Keller.

Now that the Blue Jays and Yankees have joined the conversation for Keller with the Mets and Cubs, Keller's value just continues to go up. If this turns into a bidding war, Pittsburgh could walk away with a massive haul that could change the outlook of the organization, depending on how much of Keller's contract they're willing to eat.

The two AL East rivals do not want to miss out on a splash this deadline, especially if that means one of the high-priced names on the market, Keller, ends up in the other hands.

Could that mean Pittsburgh lands Arjun Nimmala or Spencer Jones? We can only hope that is the case in these negotiations, or Cherington will end up wasting even more years with Paul Skenes. If the Pirates are aiming that high, they'd better not expect full relief of Keller's deal. Otherwise, if such a deal is financially motivated, the package will be a lot less impressive. Both of those names currently appear untouchable, but you never know, as the conversations escalate...

These rumors just keep building off of each other, potentially leading to a huge deadline for the Pirates.