The No. 3 overall pick by Boston in the 1997 NBA draft averaged 11.1 points and 4.3 assists while starting 44 of 51 games for the Celtics as a rookie and imagined being a Celtic for years.
But it just wasn't enough. A "win-now" mentality imposed by management on Rick Pitino, who was in his first season as the Celtics coach, was the start of Billups' travels through five teams over a stretch of five seasons.
"I don't know. I just think that I got caught up in a situation because I was playing well. I was starting. Rick signed for a lot of money. Everybody thought I hated Rick and Rick hated me. That wasn't the case," Billups said Friday while discussing the trade that sent him to the Toronto Raptors for fellow point guard Kenny Anderson.
"At the end of the day when I got traded, he just basically told me that there was a lot of pressure on him to win. He needed to get a veteran point guard to try to help him do that. He basically didn't have time for me to kind of learn through my mistakes. It was tough for me to get traded at that point in my career. Third pick of the draft, you feel like you're going to be there for like nine or 10 years or your whole career kind of like Paul has."
During his first couple of years after the trade, the recent Knicks acquisition said he would use the trade as motivation to beat the Celtics, but no longer sees it as an "extra incentive other than the desire to win."
Billups, a veteran with 139 games of postseason experience and one NBA title, will face a test when it comes to containing the quick and athletic Celtics All-Star guard, Rajon Rondo, in the first-round series that starts Sunday night at Boston.
Billups, the MVP of the 2004 NBA finals, had nothing but praise for the 25-year-old point guard who has become an integral part of Boston's recent run as one of the top teams in the Eastern Conference.
"He's a tough matchup because he's so fast. He's a smart player. He's crafty. He's really the engine for that team. Although they got a lot of Hall of Famers on that team, he is kind of the guy that makes you go," Billups said.
Billups believes Rondo is the only other player in the league besides Dallas' Jason Kidd who can dominate a game without scoring. So he was surprised Rondo was the last player cut on the U.S. squad that won the world championships in Turkey last summer.
"I don't really know the details," Billups said. "He was playing good. He and I were both starting in the backcourt pretty much. They just made the decision that they wanted to move forward without him. He had a great summer. He played well. Guys liked him. It was good."
Mike D'Antoni knows the Knicks will have a tough time containing Rondo and lauded his play. The Knicks coach said although the defensive assignment would go to Landry Fields at times, it will be Billups' job from the tipoff.
"We're not going to be tricky right off the bat," D'Antoni said. "I see Rondo as one of smartest players in the game. I do know that from being around him at USA Basketball. He's a big key for them without a doubt. He's always come through, so I'm expecting the best from him knowing that he's good, he's really good."
While Billups had to fight through a pair of thigh injuries since the Knicks acquired him from Denver along with Carmelo Anthony, Amare Stoudemire is confident in the job his teammate would do against the younger Rondo.
"I think Chauncey is a sound vet. He knows what it takes to win. I have the most, high confidence in him. Rondo obviously is a seasoned player. He knows what he's doing. He's very crafty," Stoudemire said.