The 2026 trade deadline is just over seven weeks away.

Trades are one of the most entertaining parts of the MLB season for fans, but for general managers, it must be a delicate balancing act: reinforcing the roster but also ensuring the other GM is happy about the transaction. Nobody wants to get fleeced, as the best trades are always win-win.

With 29 trade partners out there, there are always executives that teams would prefer to deal with, either due to familiarity, their knowledge of that team’s farm system and big league roster, or openness to explore a deal.

Everybody has their favourites, and considering the Blue Jays’ track record of trades over recent years, you can tell Ross Atkins has his preference of which GMs he likes to work with. If Toronto has an interest in rekindling trade talks heading into this year’s deadline, these three teams might be Atkins’ best options to tango with.

General managers must always have their old faithfuls in their contact list they can tap into and know a transaction is on the horizon. That must be the case between the Blue Jays and Cleveland Guardians, as Atkins and Blue Jays’ president Mark Shapiro both worked for the Guardians. Since 2010, the two teams have linked up for 19 trades.

The most recent deal came at last year’s trade deadline, when the Blue Jays received Shane Bieber, who was still rehabbing from Tommy John surgery. Although the Blue Jays parted with prospect Khal Stephen, the move proved fruitful as Bieber pitched important innings for the Blue Jays down the stretch and into the playoffs.

And with Bieber set to return to the starting rotation soon after activating his $16 million player option, it’s like the Blue Jays are receiving a second year of that deal as a bonus.

In the not-too-distant past, the Blue Jays also received Myles Straw and Andrés Giménez in the same offseason from Cleveland. At the time, the Straw trade was panned by observers, as it failed to net the Blue Jays Rōki Sasaki in contract negotiations. Straw, however, was a valuable piece to the Blue Jays’ playoff run.

Giménez is now the starting shortstop for the Blue Jays, and while the deal was basically a salary dump for the Guardians to get out the final five years and $96.5 million remaining on his deal, when healthy, Giménez has been a solid contributor for the Blue Jays defensively at a premium position on the diamond.

Pour one out for Minnesota Twins fans, because every time they see Louis Varland post a dominant outing like he did earlier this week against the Red Sox, they’re probably cringing at the thought he could still have been a Twinkie. And yes, Varland is under team control through the 2030 season, for the next four-plus seasons.

With the passage of time, the Varland trade looks worse and worse for Minnesota, while the 28-year-old has blossomed into one of the best relievers in baseball and is surely headed to the All-Star Game in Philadelphia.

Let’s also not forget the Blue Jays re-acquired Simeon Woods Richardson from the Twins a few months ago, and he’s doing fine in a secondary bulk role in Toronto’s bullpen. Woods Richardson was also a centrepiece to the José Berríos trade back in 2021, which also included first-rounder Austin Martin heading over to Minnesota.

Considering the Twins cleared out most of their coveted trade pieces last season, there’s not much meat left on the bone, but players like Kody Clemens or Joe Ryan would be welcome additions to the Blue Jays at this year’s trade deadline.

These deals may have been two of the biggest under-the-radar trades in recent memory for the Blue Jays. Did anybody bat an eye when Toronto shipped Nate Pearson out of town for Yohendrick Piñango and Josh Rivera? Closing the chapter on highly touted prospect Pearson was the headline, not the players the Blue Jays were getting in return.

Brendon Little has experienced his ups and downs (as he works his way back to carve a spot into the Blue Jays bullpen), but he established himself as a big leaguer dating back to his 2024 debut with Toronto.

Piñango has been one of the bigger surprises on the Blue Jays, coming out of nowhere to command time in the outfield. With 0.4 fWAR on the season in 41 games, he’s been a role player for this club in the first half.