Making 27 million doesn't mean what you think it means.
actually, I'm not sure 27.7M means what you think it means
But here's the bottom line on that: next summer he'll be a just-turned 27 year old unrestricted free agent. The salary cap will be going up 10%, so if his current salary is warranted then he'd sign for around 30M next season
but clearly, he won't be getting that. You mentioned his numbers...all this year's numbers have shown is that his best efficiency happens when he's a lower-usage backup playing less than 30 minutes a game; in the case of this season, less than 25 minutes.
* The NBA average for PER is 15.0. His career mark is 14.0 and he's had only 2 seasons above the average and 6 seasons below
* the NBA average for winshares/48 is .100. His career mark is .061 and he's never been above the average.
* the NBA average for BPM is 0.0. His career mark is -1.1 and he's been a net negative in 7 of his 8 seasons
and for any team that values defense....yikes! Ant has consistently, year after year, been at the bottom of his team's ranking in defensive rating and DBPM. And guess what, Simons is dead last on the Celtics in both defensive categories this season
to summarize, Simons is an undersized SG who in reality is really a tweener guard with no capacity to play wing, and no 3-and-D and two-way skills. He's one of the absolute worst defenders in the NBA. He can shoot from the perimeter, and he has just enough passing ability not to be one-dimensional, but that's only on one end of the floor. I think if you asked Blazer fans who they'd rather have as a backup guard, Simons and his warts or a healthy Blake Wesley and his warts, most, by a wide margin, would choose Wesley
so the question is will Simons even get more than an MLE contract next summer?