USA TODAY Sports

With roughly a month until the beginning of the 2023-24 NBA regular season, there is never a shortage of stories floating around the basketball universe. 

Wednesday was a perfect example of that. Portland traded franchise player Damian Lillard to the Milwaukee Bucks in a three-team deal (which also included the Phoenix Suns). In the process, former UCLA Bruins stud Jrue Holiday was dealt to Portland. 

While leaving a team you won a Championship with is never easy, Holiday gets to head back to the West Coast. Originally from LA, you'd think he'd be somewhat happy being closer to family and friends. According to reports, Jrue might want to keep his bags packed. 

According to famed NBA pundit Shams Charania, three Eastern Conference contenders are reportedly pursuing Holiday via trade: Toronto, Miami, and Boston. 

Holiday is an excellent asset for Portland to possess. Yet, he doesn't fit the timetable with the rest of the roster. Being able to flip him for a quality wing, draft picks, or presumably both would go a long way toward expediting the rebuild. 

Stylistically, Holiday makes sense for Miami. He's unselfish, gritty, defensive-minded, and -- above all else -- a winner. However, if talks between Miami and Portland were stalled over the Heats' potential Lillard trade package focusing around Tyler Herro, we aren't sure Miami has enough to satisfy Portland with a deal for Holiday (unless a third team is in the mix). 

Toronto could use an upgrade in the backcourt. With that said, the Raptors seemingly were unwilling to part with any of OG Anunoby, Pascal Siakam, or Scottie Barnes for Lillard. Surely, none of those three will be on the table for Holiday. Again -- do the Raptors have enough assets to get a deal done? 

Boston is in somewhat of a similar boat. Holiday would be a fantastic fit alongside Jayson Tatum and Jaylen Brown. But what could the Celtics offer? Presumably, it would be a picks-heavy package. There isn't much on that roster when it comes to good, young players. A Malcolm Brodgon-Robert Williams deal won't get it done. 

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