A former manager of the Boston Red Sox owns an unfortunate place in baseball lore, to the degree that he's part of a phrase used to describe an employment situation that executives refer to around this time of year: a Grady Little moment.
When the Red Sox were a powerhouse in 2003 -- winning 95 games in the regular season, vying with the Yankees for American League supremacy all season -- there was no thought that their manager, the 53-year-old Little, might be in jeopardy. But with his team leading late in Game 7 of the American League Championship Series, Little decided to leave a tiring Pedro Martinez in the game to pitch the eighth inning -- and even after the Yankees started to rally, he stuck with Martinez. The Yankees tied the score, then won in extra innings on Aaron Boone's homer.
That was the Grady Little moment, and with the frustration of the Red Sox fan base boiling over, he was fired. Those decisions made in one ugly inning in October changed everything.
That example feels especially relevant this October, in a year that executives and staffers around the industry believe will see relatively few changes among the heads of baseball operations as the 2024 MLB season comes to a close (current Red Sox skipper Alex Cora's three-year extension pulled a prime candidate off the market). But headed into the postseason, there are several managers and front office types who could become vulnerable to a Grady Little moment. Here are some of the biggest questions of leadership going into the playoffs and the offseason.