The Pittsburgh Pirates are once again ready to be sellers at the MLB trade deadline and according to a former MLB executive, they are 'ready to make a tidal wave' when July 31 arrives.
"The Pirates are expected to be busy sellers at the deadline with righty Mitch Keller being the headliner and lefty Andrew Heaney a solid back-of-the-rotation arm they could dangle as well," Jim Bowden reported. "Several teams are asking about closer David Bednar and set-up man Dennis Santana. I could see a scenario where they trade all four of those pitchers over the next 10 days."
The Toronto Blue Jays have been linked to Keller, while reportedly also being interested in Isiah Kiner-Falefa, a utility player who was dealt by the Blue Jays to the Pirates just last year. The Yankees on the other hand have similar interests in Keller, while also looking to upgrade their third base situation. That's leading to speculation that Ke'Bryan Hayes is involved in those talks between the Pirates and the Yankees and adding both Hayes and Keller to the Bronx Bombers would certainly be a great deadline for New York.
Additionally, the Yankees are linked to some of the Pirates bullpen arms in David Bednar and Dennis Santana - two guys that could, unsurprisingly, help the Blue Jays relief corps as well. The Blue Jays, whether they want Hayes or not, should be able to be willing to outbid the Yankees for Keller - and more.
How Blue Jays can outbid Yankees for multiple trade deadline targets
The Pirates need offense as pitching has not been the issue for this team in recent years. With young phenom Paul Skenes already on the roster and Bubba Chandler and Konnor Griffin in the system, the future looks bright for the Pirates pitching department. That bodes well for the Blue Jays who would likely like to hang on to their own pitching depth with Trey Yesavage, Khal Stephens and others making noise this season down on the farm.
The caveat is, the Blue Jays top 30 prospects are limited in offensive abundance. While Arjun Nimmala looks like a legit prospect, and is ranked No. 1 internally for Toronto, it will be a steep move to send Nimmala to Pittsburgh in exchange for Keller and IKF or Hayes. However, everyone else in that top 30 should be available for Pittsburgh to pick from.
since Blue Jays shop at the top of most markets, they're often described as 'on tilt' or 'desperate' or 'all-in' … pretty much a 2x/yr occurrence & expect it again this month … they do like the best players so maybe it's semantics, but alternate description would be 'motivated'
— Ben Nicholson-Smith (@bnicholsonsmith) July 21, 2025
The Blue Jays should have no qualms about dealing Orelvis Martinez, Josh Kasevich, Emmanuel Bonilla, Sean Keys, RJ Schreck, Adrian Pinto, Jace Bohrofen, Yohendrick Pinango, Sam Shaw, Dasan Bwon, Peyton Williams, Victor Arias or Cristopher Polanco. Left off that list is Charles McAdoo - only because the Blue Jays just got him from Pittsburgh for IKF and its very unlikely they would be traded again for each other.
It's an extensive list of potential prospects that Toronto could offer the Pirates and if they want to outbid the Yankees, they have to be willing to let go of several of these players because it appears as if the Yankees won't be willing to do the same.
The Pittsburgh Post-Gazette's Noah Hiles wrote about those players who the Pirates are looking at within the Yankees system. He says, "The most ambitious target, which would almost certainly only come in a deal that includes Keller, is switch-hitting outfielder Jasson Dominguez. Rated the top prospect in the Yankees system and No. 16 in all of baseball last year by MLB Pipeline, Dominguez, 22, is off to a solid rookie year, boasting an above-average OPS and a 0.7 bWAR.
Hiles went on to say, "If not Dominguez, middle infield prospect George Lombard Jr. or 6-foot-7 outfielder Spencer Jones, who hit 10 homers in his first 16 games in Triple-A, are a few other desirable targets. Should the deal be centered around a rental player, or even Bednar or Santana, right-hander Cam Schlittler could be an intriguing pitching project."
If the Yankees are unwilling to part with their top prospects, the Blue Jays should jump in with both feet as it's not just a matter of bolstering areas of need for Toronto, but it's a move that could block New York from bolstering theirs at the same time. For the Blue Jays they have to approach this deadline with an "everything is on the table" type of approach.
