Terry Francona
Terry Francona has the distinction of being among the top 15 winningest managers in MLB history with a grand total of 1905 victories. On top of that, his career .539 winning percentage ranks him within the top 100 managers all-time for those registering a minimum of three years at the helm.
In his 23 seasons in the league as manager, Francona has actually done for only three teams in total. His least successful stint was with the Philadelphia Phillies back between 1997-2000. With the Phillies, they never managed to finish higher than third in the NL East in each of the four seasons. But his legacy would be built shortly after that as he brought tremendous success to both the Boston Red Sox and Cleveland Indians (now the Guardians) for the next couple of decades. In total, Francona-led teams have captured five pennants, and have never finished below third in the division since 2004. Moreover, his career playoff record stands at a stellar 44-34 for a .564 winning percentage, having made the postseason in 11 of his 19 seasons with the Red Sox and Indians combined. So he knows how to get the job done at the biggest stage.
With just 95 wins away from the exclusive 2000-win milestone, Francona would be highly motivated to have the opportunity to lead an MLB team to success once again, especially for any one that has struggled over many years to win a championship. After all, he somehow worked his magic to help the Red Sox finally break the hex to win it all back in 2004 after an 86-year drought. So if Francona managed to accomplish the improbable, then just about anything is possible with him leading the way. The only thing that may stand in the way is the fact that he had some medical issues in recent years. So it’ll likely be dependent on his health, but rumor has it that he is looking to step back into the shoes once again.