9. August 1st, 2016
Blue Jays Receive: LHP Francisco Liriano, OF Harold Ramirez, and C Reese McGuire
Pittsburgh Pirates receive: RHP Drew Hutchinson
This was one of the bigger trades Atkins pulled off in his first season as the Jays general manager. He had acquired relievers Jason Grilli and Joaquin Benoit over the previous two months but this deal saw the club acquire a veteran pitcher in Liriano as well as two top Pirates prospects in McGuire (#5) and Ramirez (#6).
Liriano was arguably one of the better pitchers on the Pirates roster at the time and the deal saw them gain some payroll flexibility by trading away roughly $10-12 million left on his contract. While the Jays squad did have some holdovers from the 2015 playoff run, adding Liriano to the pitching staff helped the club reach the Wild Card once again, with the southpaw earning a 2.92 ERA through 10 appearances with his new club. Liriano also made two relief appearances in the playoffs that year, tossing a scoreless 1.2 innings against the Baltimore Orioles while struggling in the ALDS against the Texas Rangers, securing only one out while giving up two earned runs off two hits with one walk.
McGuire is still with the organization and came in handy last season when the Jays catching staff hit the IL, with the Washington product appearing in 78 games and amassing a .654 OPS. Ramirez spent a few years in the minor leagues but left the Jays via free agency after the 2018 campaign. He made his MLB debut with the Miami Marlins in 2019 and is now with the Cleveland Guardians organization, owning a lifetime .271/.308/.405 slash line with a .714 OPS through 770 at-bats.
The reason this trade ranks at number nine is because of the asset the Blue Jays gave up to acquire all three players but also because of how important Liriano was for a future trade on this rankings list. Drew Hutchinson went the opposite way for the Jays and he has struggled at the Major League level ever since, bouncing between the Minor and Major Leagues and struggling to keep runs off the board while owning a lifetime 4.97 ERA through 107 appearances.
While Ramirez never did pan out for the Jays, the club still has McGuire in the fold, for now, adding another point to the win column when it comes to the overall outlook of this trade.