It all comes back to Eric Bledsoe. Every decision the Milwaukee Bucks have made in the past two years can be traced to the moment Jon Horst opened Pandora's box and stuck a four-year, $72 million extension for his starting point guard inside. Without the Bledsoe deal, the Bucks have the cash to re-sign Malcolm Brogdonunderneath the luxury tax. If Brogdon stays, Milwaukee doesn't need to dump all of its draft capital into Jrue Holiday. If Holiday is never acquired, he's never handed a four-year max extension worth nearly double what Brogdon got from the Pacers.
No single reactionary move was indefensible in itself. Brogdon's injury issues made him a risky proposition. Holiday has been everything Milwaukee could have hoped for. If the Bucks hadn't paid him, half a dozen other teams would have competed for the chance to do so this summer. There are worse places to be than 32-17 with a two-time reigning MVP. You make the sort of expenditures Milwaukee has made specifically to get to this point.
It just goes to show just how much a single mistake can compound. It's the tragic lifecycle of most budding contenders. For every dynasty, there are 10 James Harden trades, self-inflicted wounds based on poor judgment or internal squabbles or financial fictions that topple juggernauts before they can grow into champions. The Bucks recognized their mistake early and have done everything in their power to correct it. It may or may not be enough to salvage their championship ambitions, but it created an unparalleled strain on the future that once awaited them.
In the next seven NBA drafts, Milwaukee controls only one of its own first-round picks. At a bare minimum, the Bucks will be paying the luxury tax for at least the next two seasons, three if Khris Middletonpicks up his 2023-24 option. That puts them right in range of the repeater tax should Middleton stay put afterward. The danger doesn't lie in the actual cost, though, but rather, the opportunity cost of Milwaukee's salary structure.