According to Adrian Wojnarowski of Yahoo! Sports, the Bucks made Drew's hiring official on May 30.
The fact that the Bucks hired any coach this quickly should indicate to thoughtful observers that Jennings' days are numbered. After all, one of the chief discussion topics in the interview process had to be the franchise's future personnel plans. It seems unlikely that Drew would have taken the gig if he wasn't on board with what the team wanted to do with its numerous free agents.
We know that the Bucks have already made those plans clear as they pertain to Jennings.
If Drew had strong feelings about wanting to keep Jennings over Monta Ellis, he would have been signing on to a new team with a built-in management clash from day one. There were other options out there for Drew, so the fact that he picked the Bucks indicates that he and the franchise saw eye to eye on some key issues—like the necessity of letting Jennings walk away.
Plus, Jennings foolishly cast his lot with Kelvin Sampson, the other main candidate for the job.
It's fine that the point guard wants to support Sampson, who was an assistant with the Bucks before moving on to the Houston Rockets. But doing so in such a public fashion was a tactical blunder.
Jennings quickly tried to backpedal when Drew got the job, but it's hard to know whether his endorsement was genuine or the result of realizing he'd made a mistake by backing Sampson.
Basically, Jennings gave himself a 50/50 chance of getting off on the wrong foot if the Bucks opted to hire somebody other than Sampson. That figurative coin flip didn't come up in Jennings' favor when Milwaukee agreed to hire Drew. It would have been better for Jennings to keep his mouth shut.
Of course, biting his tongue hasn't been one of Jennings' strong suits lately.
He shared an uneasy relationship with Scott Skiles, and after Milwaukee fired the embattled coach midway through the 2012-13 season, Jennings struggled to get along with interim coach Jim Boylan. His frustration ultimately resulted in a couple of benchings and snarky public exchanges.
In addition to a demeanor that has made Jennings increasingly difficult to coach, the young guard's play over the past few seasons has made him unappealing as a floor general. Jennings is undersized, seems to check in and out of games on a whim and has seen his defense decline since his rookie year. That's not exactly the scouting report of a player who can serve as a cornerstone on a winning franchise.
Drew dealt with a similarly frustrating player by the name of Josh Smith in his time with the Atlanta Hawks, so it'd be understandable if he wasn't interested in coddling yet another pseudo-star with an inflated sense of his own skills in his new assignment.
On the other hand, if any coach would be comfortable dealing with an undersized, three-guard rotation, it's probably Drew. It's highly unlikely that Jennings, Ellis and J.J. Redick all return to the Bucks, but if that happened, it would feel a lot like the Jeff Teague-Devin Harris-Lou Williams trio that Drew coached for a good chunk of his final season in Atlanta.
That's about the only factor that weighs even slightly in favor of Jennings coming back to the Bucks, and it's a flimsy one.
Ultimately, the Bucks' hiring of Drew indicates a tonal change for the organization. His coaching philosophy puts the focus on a slower pace and strong frontcourt play. It makes sense that Drew would want to wave goodbye to Jennings, whose only real offensive value is as a scorer in scattered situations.
Jennings has made it clear that he's not keen on remaining a member of the Bucks; he's been saying so for a while. Toss in the latest reports about the team's preference for Ellis—and the likelihood that Drew agrees with it—and it seems abundantly clear that Jennings' days in Milwaukee are numbered.
If the Bucks are trying to build a winner, that's probably for the best.