Jrue Holiday Reveals Unexpected Celtics Star as His Toughest Defensive Challenge Yet

Here’s a curious thought: when a seasoned pro like Jrue Holiday, fresh off his trade to Portland, points a spotlight not on a superstar but on a bench dynamo as the toughest opponent—well, you know there’s more than meets the eye. As he gears up to face his old stomping grounds, the Boston Celtics, Holiday doesn’t hold back—Payton Pritchard is the slippery, shifty nightmare on defense that even Jrue admits gives him pause. It’s wild to think—this isn’t your marquee matchup; it’s about the guy who’s clawing his way from the second unit to center stage. Pritchard’s rise, fueled by Sixth Man of the Year honors and a spot in the starting lineup, flips the script on what we expect from a rookie contender. So the big question looming here: will Holiday’s insider intel about Boston’s best-kept secret change the way the Trail Blazers wage war, or is this just the opening gambit in a season full of surprises? Let’s dive in and unpack why this rivalry might just come down to guarding the unexpected.

Orlando Magic v Boston Celtics - Game One — (Photo by Maddie Meyer/Getty Images)

Jrue Holiday is about to begin his first season with the Portland Trail Blazers, which means he will soon battle against his former team, the Boston Celtics.

Holiday obviously has very exclusive knowledge about the team and well-founded opinions about the best players in the lineup.

According to Legion Hoops, Holiday said that Payton Pritchard was the hardest player to defend in Boston.

Holiday was only playing against Pritchard during practices up until recently, but now he will battle him on the court in the new season.

Jrue Holiday said Payton Pritchard was the hardest player to defend in Boston

(via @RunItBackFDTV, h/t @Fullcourtpass) pic.twitter.com/PcfTmNZrVZ

— Legion Hoops (@LegionHoops) August 20, 2025