In 2004, Terry Francona did something no Boston Red Sox manager had done since Ed Barrow:
He led his team to a World Series championship.
In that moment, he achieved instant legend status. His first year at the helm, a historic overcoming of the hated New York Yankees, and 86 years of heartache and waiting brought to a magical, gratifying conclusion.
Three Octobers later, he led the Sox to glory once again.
But now, the legendary skipper is contemplating leaving the game behind, at least at the field level. His eventual departure is not without good reason. In Francona’s own words, it’s getting too difficult physically:
"“No. It’s getting harder. Physically, it’s getting harder… I want to enjoy what I’m doing. It’s getting harder to do that, just because physically it’s harder. I just want to be careful. And at the same time, I want to be fair to the team.”"
Francona is only 63, but with the increased propensity to hiring younger managers now, he’s actually the seventh-oldest in the league. His age is somewhat irrelevant, though, as his health issues have long accompanied and impeded his beloved career. Since before his tenure in Boston, ‘Tito’ has dealt with heart problems, knee pain, and blood clot issues, among other maladies. He estimates that he’s had 45 surgeries, with more to come after the season draws to a close.
When will Terry Francona retire?
Cleveland, where Francona has managed since 2013, says they are happy to keep him at the helm as long as he chooses. In 2016, he led them to their first World Series in two decades, a significant achievement for a team that has been without championship since 1948. They’re currently two and a half games ahead of the White Sox for the division lead, hoping for another chance to end what is now the longest drought for any team in the league.
Francona’s managerial career has not been without scandal. In the spring of 2021, The Athletic (subscription required) reported that he had been involved in covering up the sexual harassment accusations levied against former Cleveland coach-turned-Mets manager Mickey Callaway by several women. Francona’s own son publicly stated that his father had been dishonest with him about the situation.
Francona, of course, was one of a large number in the Cleveland club and around MLB aware of Callaway’s behavior, which has been called ‘the worse-kept secret in the organization.’ That does not excuse him from blame, but he’s far from the only guilty party.
It’s difficult to reconcile that involvement with the great achievements of Francona’s career. Still, when he retires, it will be a definitive bookend to a glorious chapter in Red Sox history.