Anfernee Simons’ long, strange trip in a Trail Blazers jersey is over.
Simons, the longtime understudy to Damian Lillard and CJ McCollum, has seen his star fade within the organization after playing his way into a four-year, $100 million contract while Lillard was injured at the end of the 2021-22 season. At the time, Simons appeared to be cementing himself as a franchise cornerstone. But things have since disintegrated around him, with the team moving on from Lillard and McCollum and drafting two other guards, Scoot Henderson and Shaedon Sharpe.
Simons, 26, now finds himself headed to Boston, having been swapped, along with two second-round picks, for veteran guard Jrue Holiday. Simons, one of the game’s most talented pure shooters, will find plenty of shots on a trigger-happy Celtics team that needs to replace its injured superstar, Jayson Tatum, and his 20 shots per game.
It was Simons’ play on the other end of the court, however, that sealed his fate in Portland.
The Blazers, who finished the back end of last season with a 23-18 record and the league’s third-best defensive rating, now fancy themselves as a playoff team in the uber-competitive Western Conference, and they need their third guard to be a gritty defender who can complement Henderson and Sharpe. Holiday, a six-time NBA All-Defensive Team selection and two-time champion, fits this bill as much as any player the team could have acquired. The problem is that he’s 35 years old and owed three more seasons of salary north of $30 million annually.
Assuming that he in fact stays on the roster and isn’t redirected to another team, this means that the Blazers have made a bet that Holiday will a) stay healthy into his late 30s and b) will take the team’s defense — which features supreme talents like Toumani Camara and Donovan Clingan — to another level.
Jrue Holiday (left) and Scoot Henderson (right) now share a backcourt. (Bruce Ely / Trail Blazers)
It’s also a significant bet on the belief that Henderson and Sharpe, entering their third and fourth seasons respectively, are ready to produce like the kind of players that the front office has promised they would eventually become. This hinges largely on their ability to raise their play on defense to the standard set by the rest of the team, an area where both players have struggled early in their careers, though both improved throughout last season and have the physical tools to get there.
So it has begun, then. The Blazers will now head into their first season in several years where they’ve declared that they will no longer actively try to be bad in an effort to get a high draft pick — and also one in which every member of the franchise will be trying not to think about what might happen to them when the team is sold to a new owner.
Portland’s general manager, Joe Cronin, has more or less created the kind of roster that he promised when he took over in late 2021. If the team plays next season at or above .500, its defense continues to improve, and Henderson and Sharpe take leaps forward, then Cronin will be vindicated. If not, he may be out of a job.
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