97, 103, 92, 95 wins. I’d say that’s a pretty damn good run. EDIT: Most wins in the majors in that span. 1 of only 2 teams to win 90+ all four years (Dodgers) and only the Red Sox and Indians won 90+ in 3 of the 4 seasons. where did the cubs win total from 2012-2014 rank? those seasons count too. Not for original conversation, which is "last five years." Jim Hendry was GM for 9 seasons and had 3 playoff appearances. Theo is gonna be 4/8. It'd be funny if they missed again next year and he ended up being exactly one appearance better than Hendry (and that one appearance was a play-in game loss). Sure, Theo got through the playoff crapshoot time, which was super fun but doesn't specifically reflect on him as an executive.