On August 11th, the Brewers announced that Doug Melvin was stepping down as GM and that the organization would immediately begin searching for a replacement. Their owner, Mark Attanasio "already [had] a list of names in mind for Melvin's replacement", and also hired executive search firm Korn Ferry to help with the process.
At the time, it was unclear as to who might be on that list, but according to Jerry Crasnick, a current Red Sox executive could be a target.
Jerry Dipoto was involved in a public dust-up between himself and manager, Mike Scioscia. Unfortunately, the situation was irreparable and Angels owner, Arte Moreno, felt that Scioscia was more valuable to his club, and sent Dipoto on his way. While he's helping out with the Red Sox and their transition from Ben Cherington to Dave Dombrowski, his contract does not prevent him from exploring outside opportunities for a GM position.
The Brewers are known to be looking for a candidate with a strong analytical background, which Dipoto undoubtedly fits. It was reportedly one of the reasons he didn't get along with Scioscia, but in Milwaukee, that wouldn't appear to be a problem.
Crasnick also reported that at least one MLB executive thinks a former Red Sox GM could be in the mix.
Talked to another MLB exec today who speculated that Ben Cherington is potentially a "great fit'' for #Brewers job.
— Jerry Crasnick (@jcrasnick) August 20, 2015
Cherington stepped away from Boston on August 18th, when it was announced that Dombrowski would be taking over as President of Baseball Operations. Even though he was given an opportunity to keep his position, he ultimately decided to leave.
He helped lead the Red Sox to a World Series title in 2013, but the following two years have been disappointing. Cherington's recent acquisitions of Pablo Sandoval, Hanley Ramirez, and Rick Porcello have been disastrous, although it's unclear if any of those moves were at the behest of ownership; which has meddled in personnel decisions before.
The Brewers are entering a rebuilding phase for their organization, and with the offseason starting in just a few months, they appear to be making progress in their search. Ideally, a new GM should be installed as quickly as possible, especially if it's an outside candidate.