Some thought the Detroit Pistons waited too long to trade Jerami Grant back in 2022, but they were still able squeeze a couple of picks out of the Trail Blazers in the deal. It turned out to be a big mistake for Portland.
The Blazers were trying to bolster their quality depth around Damian Lillard and immediately gave his buddy Grant a ridiculous extension through the 2027-28 season just before trading Lillard.
It was an inexplicable move if they knew they were going to trade Lillard, and now the Trail Blazers are stuck with Grant, who is in decline skill wise and has yet to even play 65 games in a season for Portland in the three years he’s been there. Portland is still on the hook for $32, 34 and 36 million over the next three seasons for Grant. Ouch.
You wouldn’t think the Blazers would make such a move again, but you’d be wrong, as last night they traded Anfernee Simons and two second-round picks to the Celtics for veteran Jrue Holiday in an almost mirror image of the mistake they made with Grant.
This makes perfect sense for the Celtics, who save five million in the deal, grab two picks and get a guy in Simons who is on an expiring deal that they can likely flip for more assets at the deadline. He allows them to compete for a playoff spot with Jayson Tatum out for the season without any long-term obligations. They also get off two extra years of Holiday that the hapless Blazers have just inherited.
I should say that I love Holiday. He’s a consummate professional who can still play, and the Blazers may think he’s the type of veteran leader who can help Portland make the kind of leap the Pistons just made.
The Trail Blazers unexpectedly won 36 games this season and may feel Holiday can help them into the playoffs. But it’s a steep cost to pay considering his contract, age and the baffling fact that they GAVE UP PICKS.
Why in the world is Portland giving up picks in this deal when they are the ones doing Boston the favor? It’s not like Simons is a bum, and he’s on a reasonable, expiring contract. Make it make sense.
Sorry, Blazers fans, but that’s the exact type of move the Pistons have to avoid.
Trail Blazers are the model for the Pistons of what not to do
Detroit showed that adding the right veterans can make all of the difference for a young team, as that it what happened for them when they acquired Tobias Harris, Malik Beasley and Tim Hardaway Jr
But none of those players were on big, long-term contracts, as Harris signed for just two seasons at a reasonable rate, THJ was on an expiring deal and Beasley signed one of the best value contracts in the NBA.
The cost of Harris and Beasley was one million more this season than Holiday’s $30 million. He’ll be making $37 million in 2027-28 when he is 38 years old.
The Pistons have to avoid these types of deals that hamper their long-term financial flexibility for an older player who may help them in the short term but would represent huge future problems.
I’m glad Detroit wasn’t involved for Kevin Durant and this deal for Holiday made even less sense.
The Pistons need to continue to seek out value deals for veterans, not overpay for a name who will cause catastrophic financial issues down the line.