The 2023 offseason was one of major change for Chauncey Billups and the Portland Trail Blazers. After 12 seasons, the team finally bid farewell to Damian Lillard, sending him to the Milwaukee Bucks in a blockbuster trade in exchange for Jrue Holiday, Grayson Allen, and a bunch of draft assets. It became obvious immediately that Holiday wasn't going to stay in Portland, with the Blazers going into a rebuild and all.

But immediately after landing with the Blazers, Holiday made sure to have a serious conversation with Billups about his future just so the head coach knows that he wants to land with a contending team, which he did shortly after the Boston Celtics traded for him.

And for Chauncey Billups, it was a big deal for him to get to speak to Jrue Holiday since it's not too often that someone who knows the feeling of getting traded by a franchise they won a championship with in a city they grew to love comes along.

“I think the biggest thing was just there’s not a lot of people that actually have been through that, that can kind of talk him through it, that he’s actually seen and he respects,” Billups recalled, per Jay King of The Athletic. “I know it was a little tough spot for him, being traded, kind of being blindsided by that. I’ve been there before. So just being able to rap with him like that because I know him.”

Much like Jrue Holiday, years after winning a championship, Chauncey Billups was traded by a franchise he loved dearly. But for Billups, the trade that brought him to the Denver Nuggets from the Detroit Pistons ended up working for him, since it gave him another chance to compete. Holiday's desire to latch on with a contending team therefore makes all the sense in the world to the Blazers head coach.

“I know where he’s at in his career. He’s not 25 where he can just (be patient). I know what he wants to play for. So it was actually a really good conversation that we were able to have even though, and obviously, I didn’t know where it would end up. But our intention was to make sure that he was going to be in a great position, a great situation,” Billups added.

“I had a great conversation with him. I did. I love Jrue, man. I love Jrue.”