The Blue Jays and Pirates Make Perfect Trade Partners

There is always one question every selling team asks itself at the trade deadline: How can they get back the best prospect package?

Sometimes the biggest advantage in trade negotiations isn’t the players being moved, it's the money that can be attached to a deal.

As the Blue Jays look more and more like sellers, that financial flexibility could become one of Ross Atkins’ biggest trade assets. Atkins has shown a willingness to take on money in previous trades. If he’s willing to do it again, one club stands out as a particularly intriguing trade partner, and that's the Pittsburgh Pirates.

The Jays and Pirates have had a consistent trade relationship in recent years. Pirates GM Ben Cherington previously worked with Ross Atkins as the Blue Jays' vice president of baseball operations from 2016-2019 before leaving for Pittsburgh. Most recently, the teams linked up in a three-team trade with Cleveland that sent Andrés Giménez to the Blue Jays and Spencer Horwitz to the Pirates. Back in 2024, the last time the Jays sold at the deadline, they traded Isiah Kiner-Falefa to Pittsburgh for Charles McAdoo.

Recently, Bob Nightengale reported that the Pirates are planning to be aggressive at the deadline as long as it doesn’t increase the payroll. For the Blue Jays, this could be music to their ears.

Imagine two clubs offer a similar prospect package for Daulton Varsho. The difference is that one team asks Toronto to cover the remainder of his salary while the other doesn’t. If the Blue Jays are willing to absorb the money, they're no longer trading just Varsho; they’re trading Varsho and payroll relief. That gives the team another bargaining chip, and it’s reasonable to expect a better prospect in return because they’re providing more value to the acquiring team.

Pittsburgh is in a precarious position. As of Sunday evening, they have a 54-52 record and find themselves just one game out of a playoff spot. The Pirates haven’t made the postseason since 2015, and with Paul Skenes still in his pre-arbitration years, their competitive window is wide open. The time to make a push is right now. 

The team does have some areas of need, particularly in the bullpen. As a unit, their bullpen has a 4.50 ERA, and that number jumps to 8.70 in high-leverage situations, so an improvement there is paramount. The Pirates could also use an improvement defensively in center field. Oneil Cruz is great with the bat, but the numbers (-9 defensive runs saved) and the eye test leave you wanting more.

Fortunately for the Blue Jays, they have players who fit those needs almost perfectly.

Varsho is on an expiring contract, and the Blue Jays will likely look to trade him at the deadline. Myles Straw fits the mold, too. Both players have a history of playing exceptional center field defense, and Varsho also offers some left-handed power. 

In the bullpen, Jeff Hoffman carries a 4.30 ERA, but the strikeout rate, FIP, and underlying stats remain in line with some of the best of his career. Game 7 of the World Series aside, he also has a proven postseason track record.

None of these players would lack suitors. Contenders consistently pay a premium for impact relievers and elite defensive center fielders. If the Jays are going to maximize their return, they shouldn’t just be shopping their players; they should be shopping payroll flexibility as well.

Taking on money shouldn’t scare Toronto. The Blue Jays already carry one of baseball’s highest payrolls, and even after selling off at the deadline, they’re unlikely to fall below the luxury tax threshold. If absorbing an additional $5 million is the difference between landing a 40 FV prospect and a 45 FV prospect, then that’s an investment worth making for a club focused on 2027 and beyond.

The Pirates could also move on from an expensive contract that the Blue Jays could take on. In their rotation, Skenes, Jared Jones, Bubba Chandler, and Braxton Ashcraft are all under control, with additional pitching on the way. Because of that, Mitch Keller and his $39 million remaining on his contract in 2027 and '28 could be expendable. Keller wouldn’t be the centrepiece of the deal. Instead, his contract could serve as the financial leverage that allows the Jays to demand an even stronger prospect package.

One player who doesn’t fit the obvious trade candidate mold is Louis Varland. Trading one of the best relievers in baseball with multiple years of control would be unpopular, but that's exactly why his value is so high. Deadline history shows controllable elite relievers can command franchise-altering returns. If the Pirates view themselves as a legitimate postseason team, then Varland is exactly the kind of arm worth paying a premium for. With the prospect package the Pirates could offer, the Jays should at least pick up the phone.

Every extra dollar the Blue Jays are willing to absorb could translate into a better prospect this deadline. The Pirates may not be the only club that fits that equation, but this trade match is a great example of how money can serve as a prospect-acquisition tool. If Ross Atkins and company are serious about maximizing every trade, their payroll shouldn’t just be a budget; it should be another asset in trade talks.

View our top trade candidates list, up to nearly 70 names and updated regularly!