Theo Epstein and the Chicago Cubs are limping to the finish of their season and the future of the franchise is in question. Similarly, Epstein's former franchise, the Boston Red Sox, are in the midst of a massive transition. Some are suggesting the two sides could reunite this offseason.
The Cubs have fallen far short of expectations this season, and they will miss the postseason for the first time since 2014. With a core that was supposed to dominate for years following a World Series win in 2016, it appears hopes for a dynasty on the North Side are over. Manager Joe Maddon appears to be on his way out and there are whispers that Epstein could step down as President of Baseball Operations.
In Boston, Dave Dombrowski was fired a few weeks ago just a year after winning a World Series. The Red Sox are saddled with a ton of bad contracts and their farm system is barren. They need a new approach if it wants to patch its sinking ship and steer it back towards championship waters.
Epstein is under contract with the Cubs through 2021. He has been in Chicago since leaving the Red Sox in October of 2011. Epstein originally took over as general manager in Boston back in 2002 and by 2004 he'd broken the most famous championship drought in professional sports. The Red Sox won another World Series under Epstein's guidance in 2007.
Epstein is only 45. He's got plenty of years left in baseball. Things with the Cubs are clearly on the downswing, and the Red Sox need help. It wouldn't be at all shocking if he found his way back to Boston.