Even though they just traded All-Star Damian Lillard, the Portland Trail Blazers are a guard heavy team with the recent acquisition of Jrue Holiday added to a young nucleus of Anfernee Simons, Scoot Henderson and Shaedon Sharpe. Blazers management is reportedly committed to shopping the All-Defensive point guard, but keeping Holiday may benefit Portland more in the short term.
Chance to Resign Holiday For Less
Holiday possesses a play style that projects to age well with time. He is under contract until 2024-25, where he is slated to make $39.4 million.
After becoming a free agent in the summer of 2025, Holiday will have just turned 35 years old and could be re-signed for a fraction of his current price tag.
He doesn’t rely on eye-popping athleticism that is prone to deteriorate with age and time to be among the league’s best floor generals.
The fact that Holiday has been able to shoot 47 percent or better from the floor and 38 percent or more from the three-point line for the last three seasons is a telltale sign that the 14-year veteran has more to offer moving forward on offense.
The Blazers will have to worry about re-upping Simons and Matisse Thybulle that same summer if they are not traded before then, and Simons in particular is on track to field max contract offers from other teams.
A Perfect Pairing With Deandre Ayton?
Holiday was one of only 22 players to score seven or more points per game as a pick-and-roll initiator and Deandre Ayton was the second best screen-and-roll man scorer in the association last season.
Holiday’s patience in reading defenses and getting to his spots opens the floor for big men to cut to the rim for easy lob finishes or dump-offs from 10 feet inward.
The duo has all the ingredients to be a lethal combination at the top of the key and open up looks for Grant, Sharpe and their other shooters on the perimeter.
A Remedy For Portland’s Issues in 2023
After a torrid start to the regular season, the Blazers tapered off due to turnovers and inside play. Holiday solves the former while Ayton is a fix for the latter.
Holiday has kept his turnovers under three a game and has not committed more than two fouls per night since he was moved to the Bucks in 2020.
His championship experience is what every young team needs in establishing a winning culture. He and Grant equip the Blazers with top defensive talent that can cut off driving lanes and force teams to shoot late in the shot clock.
The Blazers allowed 24.7 defended field goals made inside of 10 feet last year – good for No. 26 in the league – in large part due to their defense breaking down, forcing errant switches.
Guard Matisse Thybulle was acquired at the Feb. 4 trade deadline, but by that time, injuries to several Blazers thwarted a late-season push in a tight play-in race.
Free from hyperbole, a perimeter front of Holiday, Thybulle and Grant have the capacity to be the best 1-2-3 lineup on defense when sharing the floor together, when Blazers head coach Chauncey Billups opts to deploy situational lineups to calm runs or keep Portland in the mix when one of their shooting guards falls into foul trouble.
The Downside: A Hit to Someone’s Minutes
Either Henderson or Sharpe would suffer a minutes reduction in the event that the team hangs on to Simons. Both have great upside and need ample time on the floor for their games to blossom.
Should Blazers general manager Joe Cronin look to shop Simons or Sharpe in lieu of Holiday, either player possesses the value to bring in another sizable Three-and-D wing that could make Portland a serious dark horse contender for a top-six seed out West.