February 20, 2022; Cleveland, Ohio, USA; Portland Trail Blazers star Damian Lillard is honored for being selected to the NBA 75th Anniversary Team during halftime in the 2022 NBA All-Star Game at Rocket Mortgage FieldHouse. Mandatory Credit: Kyle Terada-USA TODAY Sports

'We Really Got a Chance to be Good' – Portland Trail Blazers Guard Reveals Ambitious Damian Lillard Text That Might Excite Fans

Originally posted on Hardwood Heroics | By Jordan Samar | Last updated Sep 23, 2025 8:44 AM ET

NBA veterans Jrue Holiday and Damian Lillard rejoined the Portland Trail Blazers this offseason, as the former was traded for Anfernee Simons and the latter joined via free agency after being waived and stretched by the Milwaukee Bucks.

Holiday recently revealed that he has been in constant communication with Lillard, and the two shared a positive outlook for the Portland Trail Blazers this upcoming season.

“Just chopping it up,” Holiday said about Lillard via RG’s DJ Siddiqi. “We’ve known each other for a long time now, but even when he first re-signed with the team, him texting me, ‘Man, we really got a chance to be good.'”

Jan 15, 2024; Toronto, Ontario, CAN; Boston Celtics guard Jrue Holiday (4) drives around Toronto Raptors forward Scottie Barnes (4) during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-USA TODAY Sports

“I feel like winning and competing and showing these guys that have so much talent,” he continued. “I don’t think y’all understand like Scoot and Shaedon are so athletic and so smart the way that they play the game. They’re going to be so good, and I feel like all they need is time. I feel like the time is now, because they have all the tools. I’m super excited to play with them.”

Portland Trail Blazers News: Jrue Holiday dishes on retirement plans

Jrue Holiday’s contract with the Portland Trail Blazers extends through the 2027-28 season, with a $37.2 million player option in the final year of the deal. He’ll be 37 years old by then, but Holiday said he plans to play in the NBA for as long as possible.

Nov 10, 2024; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) drives for the basket against Boston Celtics guard Jrue Holiday (4) in the first quarter at Fiserv Forum. Mandatory Credit: Benny Sieu-Imagn Images

“Just kind of going with it. I’ve been blessed enough to play for this long, and I’ve never taken that for granted,” Holiday said.

“I know this is a dream come true for most young kids, but I know 17 years is a dream come true for any 35-year-old who gets a chance to stay as healthy as possible and to play the game that they love. I’ll just continue playing until I can’t anymore,” he added.