Portland's $60 Million Trade Looks Better Amid Anfernee Simons's Poor Fit With New Team

The Portland Trail Blazers are good for one solid trade per year at this point.

In 2023, it was trading Damian Lillard and bringing back Toumani Camara as part of the return. In 2024, it was swapping Malcolm Brogdon for Deni Avdija. For this past offseason, the Anfernee Simons trade is shaping up to be the major front office win.

The Boston Celtics are on the clock to either find a trade partner for Simons or risk losing him for nothing this coming offseason. Simons is pouring in 13.1 points per game on a 43/39/88 shooting slash. Chowder and Champions' Kevin Stephan sees Simons as someone the Celtics must pawn off before the February trade deadline.

"Simons has done his job in Boston. Now his biggest value may be helping the Celtics land the final piece they need to stay in the contender tier," Stephan wrote.

Joe Cronin and Co. have done well to absolve themselves of the pressure that finding a Simons suitor would've brought. Brad Stevens is now the middleman as he hunts for a win-now upgrade, since the team is 15-10 and could have Jayson Tatum back before long. Stevens was thought to need to find a taker for Simons to get under the first luxury tax apron. Now, a Simons trade is to bring in a needle-mover like the Los Angeles Clippers' Ivica Zubac.

Jrue Holiday Can be Ideal Veteran If/When Blazers Arrive

If Holiday, the player the Trail Blazers acquired in the Simons swap this summer, sticks it out in Portland for the remainder of his deal, he could be the perfect veteran piece when the franchise officially arrives.

Holiday was on a solid pace, averaging 16.7 points, 8.3 assists, 5.3 rebounds on a 45/36.5/84 shooting slash and owning his best PER since his days with the Milwaukee Bucks before his calf strain.

If he proves ageless for a few more years, the 35-year-old would be the perfect backcourt depth piece behind Scoot Henderson and Shaedon Sharpe, while also being a strong understudy to Camara and Avdija on the wing.

Holiday isn't someone that Cronin and Co. have to think about trading unless their current direction turns out to be the wrong one.

Then again, it may be Cronin's replacement that'd be making that decision if Portland doesn't begin consistently winning soon.