Aaron Boone is the most unsuccessful successful manager in the majors.
He has been the Yankees skipper for five years. He has two first-place finishes — the only AL East titles for the organization in the past decade. Boone’s Yankees have never finished worse than second place and never missed the playoffs. Of the 211 men who have managed at least 700 games, Boone’s .603 winning percentage is fifth-best all-time.
But this hero of the 2003 Yankees-Red Sox ALCS shares similarities with a hero of the 2004 Yankees-Red Sox ALCS. Dodgers manager Dave Roberts’ .632 winning percentage is second-best. And unlike Boone, his Dodgers did win a World Series, albeit in the shortened 2020 COVID season.
In seven seasons, Roberts’ Dodgers have finished first six times. But they have won at least 104 regular-season games four times — setting or tying the franchise record for wins in each of the past three full years (2019, 2021, 2022), including 111 last season — and failed to win the World Series in any of those years.