It’s no secret that Chauncey Billups’ Portland Trail Blazers have been one of the most talked-about NBA teams this offseason—and not always for good reasons. After 11 years, seven All-Star nods, seven All-NBA selections, eight playoff appearances, and a genuine will to stay in Portland to create a true contender, Damian Lillard finally asked for a trade earlier this summer.
The 33-year-old gave his prime years to the Trail Blazers, and they responded with bone-headed move after bone-headed move. In all of his years in Portland, Lillard won only four playoff series, reaching the Conference Finals just once in 2019.
However, Lillard’s trade request (which specified his wish to be moved to the Miami Heat) has not greased the wheels on any deal to move the point guard. Portland general manager Joe Cronin even said at a press conference that a Lillard trade would take “months” of ground work to complete.
Wherever Lillard ends up, there is one question the Trail Blazers have to answer as a franchise: the Damian Lillard era is about to come to a close, so how do we move forward from here? Some people might say: new era, new regime, new coach. Well, those people would be wrong.
Rather than labelling Billups a scapegoat and kicking the former NBA Finals MVP to the curb as Portland moves into what could be a hard or soft rebuild (depending on how they manage the Lillard situation), the franchise should instead look at Billups as the perfect captain to steer this Blazers ship on a path to the promised land.

3. Trail Blazers are a guard-heavy team
One of the biggest reasons it would behoove the Trail Blazers to keep Chauncey Billups in charge during the post-Damian Lillard period is the makeup of the roster that is being left behind by the perennial All-Star.
Portland has not been shy about the fact that Anfernee Simons is at the center of what they’re looking to do in the future. The slight two-guard will instantly become the team’s best player when Lillard moves on, and under Billups, the 24-year-old has shown strong signs of improvement. It is no coincidence that Simons had a massive leap in terms of production when Billups arrived.
The year before Billups’ arrival in Oregon, Simons played about 17 minutes a game and scored 7.8 points on 42 percent from the field. With Billups at the helm in 2021-22, Simons’ numbers spiked to 29 minutes a game and 17.3 points a game on 44 from the floor. The increased minutes Billups gave Simons allowed the youngster to flourish, thereby allowing the team to move disgruntled veteran CJ McCollum at the deadline.
Simons has a great shot for his first All-Star nod this year with the increased workload, but he’s not the only guard Billups will be tutoring. Last year’s lottery pick, Canadian shooting guard Shaedon Sharpe, should also be taking a big step forward this year.
Perhaps the player who will benefit the most from having Billups as a mentor is this year’s No. 2 overall pick, Scoot Henderson. Henderson possesses the athleticism that his head coach could only dream of, but if Chauncey can teach the 19-year-old how to combine his aggressive scoring abilities with more Billups-esque floor general qualities, the sky is the limit for him and Portland.

2. This would not be Chauncey Billups’ first rebuilding experience
When you think about Chauncey Billups, you think about success. You think about those reincarnated Bad Boys Pistons teams with Rip Hamilto, Rasheed Wallace and Ben Wallace. You think of how he came in and instantly turned the Carmelo Anthony Denver Nuggets into title contenders. But before he could do all of that, the kid from Denver, Colorado had to go through some NBA hardships.
Billups was drafted No. 3 overall by the rebuilding Boston Celtics in 1998. Boston had not made the playoffs since Kevin McHale hung ’em up in 1993, and the year before they drafted Billups the Celtics won just 15 games. Billups and head coach Rick Pitino never saw eye to eye, and before he could even complete one NBA season, Billups was already being shipped up North.
Instead of unleashing him as the floor general he was, the Celtics were trying to move him between the two and the one, which stunted his development and led to his premature move away from the team that drafted him. That experience will serve Billups in good stead now that he’s coaching another lottery point guard on a rebuilding team in Scoot Henderson.
In Toronto, Billups will have seen something much different, as the Raptors brass was encouraging and backing their young star, Vince Carter. That belief in their young talent would lead to three straight playoff appearances, the first of the young franchise’s history. Meanwhile, the Celtics would continue to dwell in the doldrums for another decade before the formation of the Big Three in 2008.
All in all, Billups won just 77 games over his first three years in the league. Before he could win, he had to learn how to win, and to do that, he had to lose. As they say, you have to walk before you can run. Billups’ experiences in those harrowing circumstances make him the perfectly steady figure the Blazers need at the helm in turbulent post-Lillard times.

1. Chauncey Billups has the respect of his young core
His experience on rebuilding teams and a roster full of promising guards are both significant reasons Billups should remain the head coach of the Blazers during the rebuild phase, but the biggest one is this: he’s Chauncey freaking Billups.
If nothing else, he definitely has the respect of his players. Players say it all the time: they love to play for former players because they can trust in what those former players are telling them based on their shared experience dealing with life as an NBA player.
And this isn’t just any old player, this is Mr. Big Shot himself we’re talking about here. This is a guy who went through unprecedented turmoil in his first few years in the league only to emerge as the general of the toughest team of this milennium, a team which he would then lead to one of the unlikeliest championships in NBA history in 2004 as Finals MVP.
He’s a five-time All-Star, a three-time All-NBA selection, a two-time NBA All-Defensive team choice, and the winner of both the Sportsmanship Award and the Teammate of the Year Award. With his elite basketball IQ, the latter two acknowledgements of his character only add to the notion that not only is he a great basketball mind, he’s a great guy too.
Billups has already gotten his players to buy into the tough, defensive mentality that he absorbed while in Detroit for all of those years. And though he’s a player’s coach, he also knows when to be firm and with who, another skill he learned from his coach in Detroit, the legendary Larry Brown. Billups’ players recognize that he knows how to win, so they will take their cues from him as they look to create a distinctive identity for a new era of Portland Trail Blazers basketball.

