Admittedly, Jrue Holiday hasn't been much better than Anfernee Simons this season, especially not as of late. But if the Portland Trail Blazers were to trade Holiday, they'd likely get more value than what the Boston Celtics just received for Simons.
Boston shipped Simons and a second-round pick to the Chicago Bulls, who have been stockpiling guards this trade season. The return? A 35-year-old Nikola Vucevic, who is on an expiring contract.
Many will point to how the Celtics were able to go from Holiday's $32.4 million salary all the way down to Vucevic's $21.5 million deal. And while that makes sense from Boston's standpoint, given their financial crunch, it doesn't mean it's the best value.
Celtics' underwhelming Anfernee Simons return proves Blazers made the right call
That makes the Blazers the clear winners of their controversial offseason trade. For instance, if Portland were to flip Holiday by the Feb. 5 deadline, they'd receive a better haul than Vucevic. And let's be clear, they absolutely should be looking to trade Holiday. The signs of decline are real.
Given his downward trajectory, the fact that Portland will owe him $37.2 million with a player option in 2027-28 is concerning. That's the fine line Portland has to walk with this trade decision. Holiday has better value now, but that isn't always going to be the case if they hold onto him for too long. And unfortunately, Portland's front office has a tendency to hold onto players past peak value.
Let's hope that's not the case here, as there's a realistic scenario in which Portland's rebuild is hindered by two negative assets: Holiday and Jerami Grant.
The veteran guard should still have a market despite his poor production as of late. His borderline Hall of Fame resume and league-wide reputation should help Portland's case in this instance as well. Not to mention, the former teammate connection to Giannis Antetokounmpo, which has already led to teams like the New York Knicks expressing interest in Holiday.
There wasn't that same level of interest in Simons, whom the Celtics almost immediately put on the trade block after acquiring him for what were primarily financial reasons. The undersized offensive-minded player archetype has diminished in value around the league. Combine that with an expiring contract, and teams were understandably reluctant to sacrifice legitimate assets for a player they don't even know if they want to continue investing in.