2015 – Blue Jays acquire Troy Tulowitzki and LaTroy Hawkins from the Rockies for José Reyes, Jeff Hoffman, Miguel Castro and Jesus Tinoco
In obtaining five-time All-Star and two-time Gold Glove winner Troy Tulowitzki, the Jays finally had one of the best shortstops in the game on their side. Not only did he provide valuable production at the plate, he helped stabilize the infield defense for the Jays to help them go on two successful postseason runs in 2015 and 2016. In 238 career games with the Jays, Tulowitzki batted .250 with a .727 OPS, together with 101 runs scored, 39 doubles, 36 home runs and 122 RBI. In addition, what appeared to be just a throw-in at the time in LaTroy Hawkins turned out to be a vital bullpen piece down the stretch in 2015 as he posted a 2.76 ERA with 14 strikeouts in 16.1 innings pitched.
For the pieces that went the other way, Reyes was on the downside of his career and was a shell of his former self when joining the Rockies. Both Hoffman and Castro ended up spending numerous years in the league before finally becoming integral bullpen pieces with their current teams today. As for Tinoco, he has become a player of negligible significance. So despite the “all-in” approach by Toronto to nab the key piece in Tulowitzki, it had worked out in the best way possible in the end. That was because the Jays’ two deep playoff runs in 2015 and 2016 still remain the furthest runs they have made this century.
2017 – Blue Jays acquire Nori Aoki and Teoscar Hernández from the Astros for Francisco Liriano
Perhaps among the five best deadline trades, this one represents the closest to the situation that the Jays are in currently this season. With the Jays destined to miss the playoffs for the first time in three years and likely headed towards a rebuild in 2017, they unloaded veteran Francisco Liriano in exchange for another veteran in Nori Aoki and an intriguing prospect with enormous power in Teoscar Hernández.
Both Liriano and Aoki ended up cancelling each other out as they failed to provide any significant contributions to the team they were ultimately traded to. But the big wild card in the trade turned out to be Hernández, as he develop and become one of the Jays’ main offensive juggernauts for a good part of five seasons between 2018-2022. He would go on to win two Silver Slugger awards, as well as earning his first ever All-Star nod in 2021. This is exactly what the Jays are hoping for with this year’s trade deadline, being able to catch lightning in a bottle to potentially get the “next Hernández” to help with their future success.