Brad Stevens Clearly Soured on Long-Term Investment in Jrue Holiday

Much more context about Boston Celtics President of Basketball Operations Brad Stevens' major offseason of trading was revealed in The Stein Line's Jake Fischer's latest intel on the team's deadline plans.

As Fischer noted, the team may not be so eager to trade Anfernee Simons less than eight months after landing him by February 5. Stevens might see the current group as one worthy of being kept together.

“Yet I must pass along that sources with knowledge of the Celtics' thinking say Boston could very well elect to keep Simons, too,” Fischer wrote. “I've been told that they are willing to pay some level of luxury tax this season after the many millions they shed in the offseason by offloading Jrue Holiday and Kristaps Porziņģis.”

Brad Stevens Willing to Spend to Win, Unwilling to Spend on Jrue Holiday

It wasn't about the money. The team's new ownership group isn't pinching pennies if Fischer's latest intel bears out in the real world.

Trading Jrue Holiday in the deal that brought Simons was clearly Stevens becoming bearish on the extension he signed the former UCLA Bruin to before the team's 2024 NBA Finals run. Perhaps Stevens inked Holiday before the playoffs after the Milwaukee Bucks extended Holiday upon trading for him before their 2021 Finals run.

Stevens got to win the title but get off the long-term money, even trading him back to the Portland Trail Blazers, who Holiday never got to play for. It could turn out to be a good long-term play, but only if Boston can get back to winning. Otherwise, there will always be a "what if" attached to what would've happened if Stevens had never got rid of a proven winner.

Trading Kristaps Porzingis made sense because he wasn't there for the team's title run outside of a handful of games. Holiday was irreplaceable on that run.

Well, only if the Celtics don't do it again, that is.