The Portland Trail Blazers' one-for-one swap of Anfernee Simons for Jrue Holiday with the Boston Celtics was a head-scratching decision by general manager Joe Cronin. Holiday's production has declined, he's owed $104 million over the next three years, and he doesn't fit Portland's rebuilding timeline at 35 years old. However, the good news is that Holiday will significantly help rather than hurt the development of the Blazers' young core for several reasons.
Holiday's versatility clears path for Henderson and Sharpe
First is positional versatility, which Holiday addressed during his first media availability with the Blazers.
"I think I play every position. I've proven that and shown that throughout my career. I'm a complete basketball player. You can't put one position on someone, the way the game is changing now. Guys who have never played point guard are coming into the league and playing point guard. I'm a good fit with anyone."
Portland is bringing in aging star guards in Holiday and Damian Lillard. But with Holiday's willingness and ability to play multiple positions and Lillard's expected gap year, up-and-coming guards Scoot Henderson and Shaedon Sharpe will still have every opportunity to break out.
Even if Henderson and/or Sharpe don't wind up starting, Holiday's versatility gives head coach Chauncey Billups more flexibility in his rotations, making it easy to find a path for both to get significant minutes. Holiday's low usage rate (15.9 percent last season) will also provide Henderson and Sharpe with increased roles in those minutes, giving each of them a golden opportunity to take over as the secondary playmaker behind point-forward Deni Avdija.
Holiday will be Blazers' much-needed 'jerk'
Finally, there's Holiday's veteran leadership and championship experience. He's a two-time NBA champion and two-time Olympic gold medalist for a reason. Holiday has a league-wide reputation for being a great teammate and has consistently bought into the team-first mentality required to win at the highest level; that's something Portland's inexperienced and largely one-dimensional roster certainly needs more of.
Holiday recalled his rookie season with the Philadelphia 76ers, when Andre Iguodala was being a "jerk" to him. But it wasn't until later that Holiday realized Iguodala's harsh criticism came from a place of believing in him and seeing untapped potential.
"He was on me about a lot. And I didn't really understand why until later. He obviously saw something in me that I guess I hadn't seen yet. And just constantly being on me and harping on me about being consistent and things that I have to do were super important," Holiday said.
Now the 35-year-old Holiday is ready to fill that role for Portland, and it's precisely what they need. At this point in their careers, former top-ten picks Henderson and Sharpe remain largely theoretical players who have yet to put it all together to reach their star ceilings. Perhaps Holiday's versatility, unselfish play, and mentorship will finally help unlock that.
If so, both the trade and Holiday's contract will be much easier to justify.