A proposed trade from NBA Analysis Network would send the Boston Celtics 24-year-old Anfernee Simons, who’s due $77 million from the Portland Trail Blazers, for the team’s backup backcourt of Payton Pritchard and Malcolm Brogdon and a pair of future first-round draft picks in 2025 and 2027. NBA Analysis Network’s James Piercey believes that as the best player in this trade, he’d raise the C’s win-now ceiling and is the missing piece for a contender.

“(Simons’s) comfortably the best offensive player in this group,” Piecey prefaced before saying, “Simons is an elite floor spacer who can create his own shot in half-court sets. Simons is a fantastic player. In fact, he’s the type of player a contender could really use.”

Amidst Damian Lillard trade rumors, the Trail Blazers could look to unload a good number of their high-priced pieces; like Jusuf Nurkic, a seemingly inevitable Lillard trade throw-in. NBA Analysis Network also concocted a mock trade involving Jerami Grant being sent to the Celtics, and the Houdini didn’t approve. This one, though?

One fewer draft pick would make this a deal worth considering for the Boston Celtics

Two picks for Simons make the juice not worth the squeeze since that’d wipe out a good bit of the C’s future draft cupboard. But if Portland’s front office were to come forward with a modified package of just Pritchard, Brogdon, and one pick? Now we’re cooking with gas.

Such a deal isn’t worth considering until the trade deadline since, for all we know, Kristaps Porzingis’ presence could be the roster change necessary to get this team over the top. If the Celtics struggle between October and February, then a gamble on Simons is something the front office’s radar should feature.

Simons doesn’t solve the “pure” point guard problem some still assess to the Cs, but Derrick White might, and those two would be highly complementary in the same backcourt.