1. Marcus Stroman (and cash) Trade to NY Mets for Anthony Kay and Simeon Woods Richardson
At the time of the trade, July 28, 2019, Stroman was the Jays’ #1 starter, an All-Star, a former Gold Glove winner, had an ERA of 3.25 over 110.2 innings in the AL East, and had an additional year of control remaining on his contract (through 2020). The minor-leaguers Kay and Richardson were not in the MLB Top 100 prospects at the time, although Kay was ranked fourth in the Mets’ system at that point, and Woods-Richardson sixth. After the trade, Stroman publicly questioned why the Jays did not offer him an extension.
Update
Stroman – During his time with the Mets in 2019 after his trade from Toronto, Stroman had an ERA of 3.77, a WHIP of 1.4 and a bWAR of 1.5 over 59.2 innings. Stroman opted out of 2020 due to Covid, but in 2021 he had the 8th best ERA in the NL at 3.02 over 179 innings, a WHIP of 1.14 and a bWAR of 3.6. Last month, the 30 year-old Stroman signed a 3-year, $71m contract with the Chicago Cubs.
Anthony Kay – Now 26 years old, over the course of three seasons since joining Toronto in 2019, Kay has pitched 68.2 innings in the majors, with a 5.50 ERA, a WHIP of 1.63 and a bWAR of zero. In 2021 Kay also spent significant time in AAA, posting an ERA of 8.89 over 26 innings pitched.
Simeon Woods Richardson – Now 21 years old, he was traded by the Jays, along with Austin Martin, to the Twins in the Jose Berrios deal in late July of 2021. He is currently ranked as the #4 prospect in the Twins organization (Martin is #2).