We don't know how much Anfernee was going to demand when this contract expired (the team probably had a clue). We don't know how he felt about his future playing time in Portland. Billups got another mature voice for a very young team. Boston got a quality point guard. That's the entire deal. The draft picks were removed, probably because Jrue has some unrevealed lingering physical problem the docs or training staff noticed. Anfernee gets banged up, too. Neither of them is guaranteed to play 82 games. Portland will likely rotate starters until something gels.
There are a lot of young moving parts on the Trail Blazers.
So, considering the trade from 40,000 feet, which other defensive-minded, mature player would Portland get for Simons, knowing he will want a big salary soon? You'd have to see a need for a starting PG, be willing to consider a large contract, and have someone to offer Portland with enough defensive skill to please the coaching staff.
They had to get Anfernee out of the rotation, just as Dame had to leave. It's what's best for business.
I'm less pessimistic about the trade. Neither of them represent the future of the Blazers. Each of them should be a good fit for their new team.
https://flipboard.com/@fansided/rip-city-project-bkrnltf9z/-/a-rjS7k8_6StmD8ajxaXpANQ%3Aa%3A61877088-%2F0