In 2023, the Portland Trail Blazers made a franchise-altering mistake by signing Jerami Grant to a massive five-year, $160 million contract. Signing Grant was a half-hearted attempt to keep Damian Lillard around. Grant was playing much better at the time, but still wasn't the needle mover that the Blazers roster lacked throughout the Lillard era. Dame knew this, too, requesting a trade just one day later.
The Blazers were already trending towards a retool around top ten picks Shaedon Sharpe and Scoot Henderson, but Lillard's request officially jump-started their full-on rebuild. That made Grant's fit even worse, and Portland's decision to retain him more questionable.
ESPN's Zach Kram even named Grant's contract as the biggest mistake the Blazers franchise has made in the last five years: "All of a sudden, an expensive but understandable long-term deal looked horribly out of place, as the veteran forward no longer fit on a retooling roster."
Three seasons later, the Blazers are still trying to clean up their mess, hoping a team is desperate enough to take on Grant's remaining salary, which has lost value over the years due to declining production.
"Grant's contract hasn't gotten in the way of any other Trail Blazers moves yet — but with the Blazers rising, Jrue Holiday's hefty deal now in the fold and Grant still owed another $102.6 million over the next three seasons, it might soon prove a tricky roster-building obstacle," Kram added.
Waiving Lillard for Turner is the Bucks' version of the Grant contract
The Milwaukee Bucks now find themselves in a similar predicament with the latest developments surrounding Giannis Antetokounmpo. Their version of the Grant contract also happened to involve Lillard, which was their decision to waive and stretch his remaining $113 million over the next five seasons in order to clear space to add Myles Turner.
Predictably, like Grant wasn't the needle mover for Lillard, Turner is proving not to be the needle mover for Giannis.
The Bucks kept digging themselves a deeper hole trying to keep their superstar in Milwaukee. Fortunately, the Blazers were able to overcome the Grant mistake in their rebuild. They acquired valuable draft capital from Milwaukee, landed building block Toumani Camara, and even turned some of those assets into rising star Deni Avdija. The Bucks will likely soon look to find their own version of that trade to help them overcome the obstacles already in place, thanks to the aftermath of a failed attempt to keep their superstar around.
Giannis will net even more assets than the haul Portland received for Lillard, but there are two significant differences between this comparison. For one, the Blazers didn't send Lillard to his preferred destination, which was the Miami Heat, instead balancing the ideal trade package with a team that would still give Lillard a realistic chance to win. It doesn't appear the Bucks have the same leverage in this situation. ESPN's Brian Windhorst said on NBA Today that "it will be Giannis telling the Bucks where he wants to go," meaning Milwaukee may have to settle for the best offer from that team.
Another obvious hurdle, making it more challenging for the Bucks to successfully rebuild as the Blazers did in life post-Lillard, is that they currently can't! They don't have future draft capital because they went all in trying to make this work with Giannis.
It's a valuable lesson that teams with superstars need to learn. If things are trending downwards, you need to either proactively get ahead of trading that superstar or, better yet, add actual needle movers to convince them that things will eventually be different.
Portland accomplished neither when they signed Grant, and Milwaukee repeated that same mistake by waiving Lillard to add Turner.