The Portland Trail Blazers swapped Anfernee Simons for Jrue Holiday this offseason, paying a steep price to take on the remaining $104.4 million of Holiday's contract over the next three years. Blazers general manager Joe Cronin was willing to overlook the financial burden to help establish their defensive-minded identity under head coach Chauncey Billups.
In theory, there's no better addition to help achieve that vision than Holiday, a six-time NBA All-Defensive selection. However, at 35 years old, it's fair to wonder how much gas Holiday has left in the tank.
Bill Simmons recently brought up that concern on The Bill Simmons Podcast, noting that he saw a decline on the defensive end from Holiday, particularly in their playoff series loss to the New York Knicks.
"I didn't love the Jrue Holiday season last year, and I say that as somebody that loves Jrue Holiday," Simmons said. "I thought it was alarming that he couldn't guard anyone on the Knicks because I thought a year ago, he's somebody who could've guarded all of the Knicks. In that Knicks playoff series, I was really surprised that he wasn't at that same level."
Will Blazers regret the Jrue Holiday trade?
Simmons mentions that the Blazers are paying Holiday, Jerami Grant, and an injured Damian Lillard a combined $77 million this season, which increases to $88 million in 2027-28. At that point, Holiday will be 37 years old! That's certainly not ideal, especially considering he's already shown signs of decline.
"It's really bad cap management, I'm just going to say it," Simmons added. "When we have the second apron, that's just a lot of money to pay for those guys. I don't agree with it."
The Lillard signing doesn't deserve to be bunched in the same group as the Grant and Holiday decisions. If anything, Lillard's three-year, $42 million deal seems like a team-friendly deal given Portland's situation. They don't expect to make a playoff run this season, which aligns well with Lillard's recovery timeline. Given how steep contracts are these days, even paying that amount for two years of Lillard seems reasonable, factoring in the possibility that he returns somewhat close to form.
The other two contracts are much more difficult to justify.
In 2023, Portland signed Grant to a five-year, $160 million contract in a half-hearted attempt to keep Lillard around. That immediately backfired as Lillard requested a trade just one day later. To make matters worse, Grant has rapidly declined since and is now coming off a season in which he averaged 14.4 points while shooting 37.3% from the field. Because of his underwhelming production and massive contract, Portland is stuck with one of the top negative assets in the league.
That's what makes the Holiday addition so puzzling. Now, the Blazers have to overpay two veterans for multiple seasons. Both are trending in the wrong direction, and neither fits Portland's rebuilding timeline.
That could become a fatal flaw in the Blazers' rebuild as their veterans continue to age and they have to juggle retaining their young core.