By trading for Jrue Holiday, the Portland Trail Blazers have given head coach Chauncey Billups something of a carbon copy of himself. A 6'4" guard who can defend multiple positions, space the floor, convert from midrange, and provide invaluable leadership, Holiday checks the very boxes Billups did during his Hall of Fame playing career.
It's unclear what type of value Holiday can provide on a nightly basis at 35 years of age, but with him in the fold, Portland can move forward with several key questions answered.
Holiday has spent the past 16 seasons racking up accolades and establishing himself as one of the best two-way players of his generation. He's a two-time NBA champion, two-time All-Star, and six-time All-Defense honoree who has finished in the top 10 in voting for Defensive Player of the Year on five different occasions.
Coupled with two Olympic gold medals and the fact that he won his NBA championships with two different franchises, Holiday has a strong case for an induction into the Hall of Fame.
Now joining a Trail Blazers team that appears to be ascending the Western Conference, Holiday's job description has changed. He's no longer complementing stars such as Giannis Antetokounmpo or Jayson Tatum, but instead is being leaned on to help younger teammates come into their own.
Thankfully, a potentially symbiotic relationship between Billups and Holiday could unlock Portland's potential as soon as the 2025-26 season.
Jrue Holiday can play the Chauncey Billups role for Billups' Blazers
Billups is no stranger to entering a new situation and being immediately tasked with helping talented players realize their potential. He did so with the Denver Nuggets in 2008-09, when he was 32 years old at a time when players weren't often playing at a star level beyond that very age.
Most expected Billups to be exiting his prime, but he instead helped Carmelo Anthony and the Denver Nuggets make their first Conference Finals appearance since 1985.
Holiday is admittedly entering a different type of team dynamic, but Portland is on the rise. It went 13-28 over its first 41 games in 2025-26, only to produce a record of 23-18 during the second half of the season—a mark fueled by the play of the current up-and-comers.
Players such as Deni Avdija, Toumani Camara, Scoot Henderson, and Shaedon Sharpe seemed to simultaneously make a leap as Portland suddenly played at a postseason-caliber level.
Camara, 25, emerged as a top-tier defender, earning All-Defensive Second Team honors in just his second season. Avdija, 24, took a massive step forward as an all-around player, averaging 20.6 points, 8.2 rebounds, and 4.6 assists over the Trail Blazers' final 41 games.
Henderson, 21, improved his field goal and three-point field goal percentage from his rookie year, and Sharpe, 22, had four of his six 30-point games after the midway point of the season.
That only scratches the surface of the untapped potential on Portland's roster, which Holiday will now be asked to help highlight. Thankfully, he's the epitome of consistency as far as effort is concerned, capable of setting the tone for the teams he plays for and helping to establish a winning culture.
Holiday may not dominate the box score, but much like Billups, his impact could permeate throughout the organization as Portland takes a considerable step forward.