The clock is already ticking on Milwaukee's biggest gamble, and Christmas might be the deadline that tells us whether or not the Bucks' front office just made a franchise-altering mistake.
That's at least according to a few ESPN insiders who are already sounding the alarm: they say if the Myles Turner experiment doesn't have the Bucks firmly in East contention by the holidays, the regret will hit harder than a Giannis dunk.
"If the Bucks and new addition Myles Turner aren't firmly in contention by Christmas, there might be a whole lot of regrets in Milwaukee. Waiving and stretching Lillard, and thereby hamstringing Milwaukee's financial flexibility for the next half-decade, will pay off only if the Bucks can win now. They might not be able to, despite their strong frontcourt, because their perimeter talent is so weak," Zach Kram wrote.
ESPN says Milwaukee will feel the bite of the Turner signing by Christmas
Look, the Milwaukee Bucks made the moves that were right in front of them (thanks to an equally puzzling blunder by Indiana), but the math is as brutal as it is unforgiving.
Milwaukee waived and stretched Damian Lillard's $113 million contract, creating a financial sinkhole that will haunt their salary cap for the next half-decade. That desperate move was supposed to create the flexibility needed to retool around their championship core, but instead of spreading that $27 million across multiple impact players, they bet everything on Turner.
The perimeter talent concern is looking like a major concern as early as now, with their point guard rotation consisting of Kevin Porter Jr., Ryan Rollins, and Mark Sears.
Turner's rim protection and spacing might upgrade their frontcourt, but Milwaukee's backcourt depth remains a disaster. They're essentially asking Turner to be the missing piece on a puzzle that's still missing several other crucial components.
Bobby Marks, in particular, called the decision to waive and stretch Lillard's contract "the last option the Bucks had to improve their roster."
"We can debate the process on how Milwaukee spent the $27 million in available cap space on one player, Turner. For a team starved for depth (and also in need of a starting point guard), wouldn't it have been better served to open up room before June 30 and then split up the money on three players, not just one?" he asked.
And that's exactly the question that will haunt Milwaukee if this season goes sideways.
Turner averaging the 15, six, and two he did a year ago won't matter if the Bucks can't find consistent guard play or bench scoring. Because the truth is they did initially have the room to address their roster holes, but instead chose to make another expensive bet on a player whose impact may not single-handedly fix their deeper issues.
History tells us the Christmas timeline isn't at all arbitrary -- it's when championship contenders separate themselves from the pretenders and the bottomfeeders.
And if Milwaukee is sitting outside the top five in the East by then, Turner's defensive presence won't mask the reality that they misallocated their cap space in a bid to keep Giannis Antetokounmpo happy in town.
Fans likely don't feel it yet at the moment, but the fact is that the opportunity cost of $27 million could have landed them a starting point guard, a reliable sixth man, and depth pieces that address their bench scoring woes. And that cost is going to follow them down the line and compound as the Bucks find fewer avenues to build a team around Antetokounmpo.
In the wake of the flexibility they could have had, they're now banking on Turner's two-way impact being enough to elevate a flawed roster to championship level.
The irony is crushing: in trying to avoid regret over the Lillard situation, Milwaukee may have created an even bigger one. Turner will have to be worth every penny of that stretched contract, because the Bucks won't get another chance to fix their mistakes for years.