The offseason isn't over by any means, but up until this point, the Portland Trail Blazers' moves have been largely underwhelming.
Trading for Jrue Holiday was puzzling yet exciting, as it suggested that general manager Joe Cronin would continue making complementary follow-up moves to help the Blazers return to the playoffs. Instead, they have nothing to show for it outside of the controversial selection of Yang Hansen with the No. 16 overall pick.
The Blazers' free agency inactivity is understandable given their rebuilding situation and their desire to preserve long-term financial flexibility. But that does contradict their trade for Holiday, who has one of the worst contracts in the league at three years, $104 million.
The only way to make sense of this is for the Blazers to flip Holiday... again.
Joe Cronin still has time to fix his Jrue Holiday mistake
After Portland reacquired Holiday, many speculated that they did so with the intention to flip him, because well, that's the logical thing for a team in the Blazers' position to do with a 35-year-old guard. However, that doesn't appear to be the case, as Sean Highkin of Rose Garden Report notes that the Blazers intend to keep Holiday this time around. That's a potentially catastrophic mistake for Cronin and the Blazers.
In a different timeline -- one where either the Blazers are ready to contend or Holiday is ten years younger -- this trade makes perfect sense. He's a much more impactful two-way player than Anfernee Simons and better aligns with the defensive-minded identity that Cronin and Chauncey Billups have established over the past few seasons.
But the Blazers' win total is set at 33.5 for next season on DraftKings. They aren't making any noise this year, even with Holiday.
Despite Portland's discouraging win projection, there are reasons to keep Holiday around. He'd be a valuable mentor for Scoot Henderson and can be a true veteran leader with his league-wide reputation for being one of the best teammates.
If adding Holiday is the missing piece to get the Blazers into the Play-In Tournament, it will be a valuable experience for their young core. Additionally, the fact that Holiday is 35 and declining means there's a clear pathway for Henderson to eventually take over as their long-term starting point guard.
That said, the cons of keeping Holiday around significantly outweigh the pros for Portland.
His numbers significantly dipped during his two seasons in Boston, partially due to injury. The Blazers had to revise the trade and take back their two second-round picks because of concerns surrounding Holiday's medicals.
His massive contract is already one of the worst in the league. And the fact that Holiday isn't fully healthy means there's a scenario where the Blazers are paying an injured 35-year-old guard that amount of money (while also being on the books for another negative asset in Jerami Grant).
The Blazers' plan could be to flip Holiday to a contender at the deadline. But why take that risk?
Holiday should already have interest from teams around the league as is, such as the Dallas Mavericks or Sacramento Kings. Keeping him around also limits Henderson and Shaedon Sharpe's roles, potentially hindering their development.
Trading him immediately is the logical risk-averse approach in that it prevents all of these disastrous scenarios from occurring. And it needs to happen sooner rather than later.