Unfortunately for Boylan, being retained and coaching his first full season won't happen this time around.
Compiling a 14-13 record since the team and Scott Skiles parted ways, it's not as though Boylan has been bad. The problem lies in the simple fact that he hasn't been good either.
Under Skiles, the Bucks didn't exactly come sprinting out of the gates.
At 16-16, they struggled to find any sort of identity. While the blame for that can be dispersed out among management and Skiles, it hasn't helped Boylan.
But that's not an excuse.
Milwaukee has a hodgepodge of talent. It's not a perfect puzzle and all the pieces don't necessarily fit. The talent is there though—making the pieces fit falls on a head coach's shoulders. Is that fair? Maybe not, but it's the nature of the business.
For example, a backcourt combination of Brandon Jennings and Monta Ellis was a crazy idea to begin with. Both players thrive when they possess the ball. That doesn't mean the offense should be in complete disarray though.
Prior to the arrival of J.J. Redick at the trade deadline, that wasn't far from the truth.
As isolation after isolation play was run for Jennings and Ellis, the other three players on the court became ball-watchers. There was a lack of movement and no efficiency. Meanwhile, Boylan didn't implement change.
Despite ranking 13th in points per game, the Bucks rank 24th in field-goal percentage. With a more efficient offensive game plan, the gap between these rankings could potentially decrease and lead to more wins.
Defensively, they're 19th in opponents points per game at 99.5. While that isn't a number to be proud of, the problem comes back around to the inefficient offense.
That's not all Boylan's fault, but at some point you have to try some new things. It has changed a bit with Redick, but it might be too late to really matter in terms of making a legitimate run in the postseason.
He's had his share of head-scratchers lately as well.
First, there was the strange handling of John Henson's minutes last Saturday against the Toronto Raptors. In the first half, Henson scored 8 points and grabbed 2 rebounds in just under nine minutes. In the second half, Henson got off the bench only to cheer his teammates.
On Monday, Boylan made another mind-boggling decision late in an overtime game against the Utah Jazz. As indicated in Charles Gardner's live blog for the Milwaukee Journal Sentinel, Boylan had Redick—one of the league's best free-throw shooters—throwing the inbound pass.
Yes, Redick is an improved passer that doesn't often make mistakes. But there is absolutely no reason for him not being on the receiving end of a pass in those situations.
It's not fair to say Boylan isn't head coach material. He's been thrown into difficult situations twice now in his career. But if he has the talent, there are teams out there that will give him the proper chance.
Sadly, the Milwaukee Bucks can't afford to be one of them.