Through Chauncey Billups' precise, involved coaching, the Trail Blazers can see a championship path

CLEVELAND — Chauncey Billups carries the feeling, the moment he felt he was turning the corner but was issued a harsh reality from a coach who was nearly impossible to please.

Larry Brown pulled Billups aside for what Billups thought was going to be a compliment. Instead, Brown was maddeningly frustrated.

“You have no idea how to play point guard for me, do you?” Brown said, erasing all the good vibes Billups had in the moment.

This was in the first month of the Brown-Billups relationship, possibly after a 33-point performance in a road win against Memphis.

Brown was in his first year as Pistons head coach; Billups his second, but on his fifth team after a journeyman road.

“I thought what I had was an incredible game. When he said that, I was like, ‘What?’” Billups said incredulously to Yahoo Sports recently. “And we ended up spending time the next few days watching film together.

“I give Coach Brown all the credit for making me understand. There’s a scoring point guard, to what I came under him, [and] a point guard who can score. Two different things. I didn’t know that. And then I became a point guard who could score. It changed my career. It changed my leadership, everything I did from that point forward. It shaped me.”

Brown was so precise, rumor has it, that he spent the better part of 30 minutes during practice schooling then-rookie Darko Milicic on the angle of a screen.

Several months later, Brown and Billups tasted champagne as the Pistons beat the Lakers in the 2004 NBA Finals, cemented in history as championship coach and Finals MVP, respectively.

What Billups didn’t realize was those moments would come to mold him in his journey to become a head coach, a position he never thought he’d hold but one he seems perfectly comfortable in and suited for, roaming the sideline for a more versatile and dangerous Portland Trail Blazers squad.

The Trail Blazers started hot, then tailed off a bit when Damian Lillard missed a chunk of games due to a calf injury but have begun to rebound in a treacherous Western Conference. If not for an improbable Jamal Murray triple with 0.9 seconds left, Portland would be 14-11.

The Blazers have gone through a pretty rough portion of the schedule and have forged a defensive identity that hasn’t been present over the past decade.

But with the way this roster has been transformed over the past year or so, there's a feeling that it will be more playoff-ready. On the floor, of course, everything revolves around Lillard. Players such as Josh Hart augment the defensive pressure the Trail Blazers want to apply.

And the direction comes from the second-year coach, who spent most of his first year teaching and figuring out that he can be as meticulous as that head coach who gave him fits.

“I lost a lot of sleep [with Brown],” Billups said. “I knew how that made me feel. I don’t want my guys to feel that way. Now, they’re gonna be upset with me at times. Because the truth don’t always feel good, no matter how much you finesse it. But they know how much I care, and they know it’s coming from the right spot. Which allows them to have some patience.”

And for him to have patience with himself. Billups knew he would have a future in basketball beyond his playing days, but coaching found him. He openly talked about wanting to head basketball operations, but always bristled at the notion of coaching.

He interviewed a couple of places and was even offered the top spot in Cleveland. But the situation seemed unstable, so he stayed doing television with ESPN — and was good at it.

“My biggest gift, touching and leading somebody every day. It’s how I was as a player," he said. "As I started to figure out, from that [general manager] seat, you can’t do that with the players. You gotta let the coach do that with the players. You gotta have a little distance.”

His second cue was moving from the TV desk to the booth, doing color commentary for the LA Clippers. He started to watch opposing coaches, and he found himself preparing differently because of the proximity to the game.

“The chess match is going on,” Billups said, smiling. “Now that’s starting to spark me. I’m starting to look at it like I’m a point guard, like I’m actually playing.”

The pandemic turned out to be the final thing to nudge him in that direction. Current Clippers coach Ty Lue — still an assistant to Doc Rivers — was with the Billups family in Colorado during the shutdown.

The time opened the door to Lue making Billups his assistant when he slid over to take the Clippers job.

Lue had been in his ear from the tail end of his playing days, telling him, “Chauncey, you’re a coach. Be a coach.” They spent days and nights going over philosophies and sets. Billups’ wife, Piper, sat and watched as her husband would come to bed late at night, with a notepad, drawing up plays.

She wouldn’t say anything, but she was taking notes of her own.

When he finally confessed it was what he wanted, she said, “I know.”

“And she knows me. She knows I’m always chasing something. I gotta be, I’m so driven. I’m chasing greatness, I’m chasing success. And if I’m not, she probably doesn’t want to be around me.”

It’s not hard to foresee Billups in the perch running a team in the future, but he’s diving full force into coaching.

That passion has translated to the Trail Blazers, a franchise that has been consistently good but hasn’t been able to break through to the Finals in this Stephen Curry era of Western Conference dominance.

These days, Lillard looks back to his old form and nearly single-handedly pulled off a win over Denver with some old Dame Time magic, scoring 40 for the third time this season and adding 12 assists. He looks refreshed, to say the least.

Lillard needed the break, whether he knew it or not. Carrying the franchise year after year, answering the same-old questions — “Why did you stay?” or “Why not go after a better situation?” — can undoubtedly get bothersome. He called last season “a blessing in disguise.”

“Last year was a real reset for me. It’s been a tough year,” he told Yahoo Sports. “Personally, dealing with the injury, fighting myself back, being at home so much, being away from a game, and then, you know, life is happening. While all of these things are happening professionally, life is still happening during that time. That just created some hurdles.”

He was able to sit back, watch all the changes take place in the front office and on the floor and even pay attention to the unflappable Billups through it all.

In their first conversation as coach and star player, Billups asked Lillard an important question, one he repeated to Anfernee Simons and others on the Trail Blazers’ roster: “How do you want me to coach you?”

Lillard’s reply was easy: “Coach me hard.”

“That’s what I come from, my teachers and father figures in my life were very particular people,” Lillard said. “It wasn’t strict. I wasn’t sheltered. [But] it was one way for it to be done. You just got to trust it, the fact that my intention is right, and I want the best for you. When you’re trying to get that type of point across, it’s not always gonna be gentle. It’s not always gonna be, you know, welcoming. It’s not always gonna be warm, but it’s coming from the right place.”

Getting buy-in from the franchise star was critical, especially with what was ahead: Neil Olshey being replaced by Joe Cronin, first as interim, then as permanent general manager. Then came the trade of C.J. McCollum, which opened the door for Simons to play, make mistakes and grow to the point that the Blazers signed him to a four-year, $100 million extension this offseason.

Simons looked like Billups’ pet project last season, learning how exact Billups can be while also being given a level of freedom he hadn’t experienced as a pro.

He agreed when it was suggested that Billups is more involved and precise than most coaches, and he also said it helped.

“It gave me a lot of confidence. I knew I could play at the highest level and be a good point guard,” Simons told Yahoo Sports. “I’m used to somebody being hands-on. He’s gonna be on me. It’s a good dialogue of how he wants you to play. It’s nothing I can’t go back and forth with him about. It’s been great so far.”

Simons is secure. Jusuf Nurkic has been available and impactful. Free agent addition Gary Payton II should be back soon following offseason core surgery.

Both Lillard and Billups made note of the support from the front office and team ownership, which resulted in Lillard signing another extension that will keep him under contract until the 2026-27 season. And he was instrumental in Jerami Grant coming over from Detroit in the summer.

Grant is in a sweet spot of sorts. While in Denver in 2019-20, he was never going to be afforded the opportunity to develop beyond being a fourth option — maybe. He was viewed league-wide as a long, rangy defender but an afterthought on offense. Signing a free-agent deal with Detroit allowed him to grow and, for a short while, be the No. 1 option.

He was a revelation, taking yet another step in Year 7, averaging 22.3 points and 4.6 rebounds but perhaps miscast as the Pistons started a rebuild.

The Pistons’ developmental track and Grant’s age (28) meant the two sides weren’t a great fit long-term. Billups coveted Grant, and so did Lillard, dating to their time on the U.S. Olympic team.

In July, everyone got their wish when Grant was traded to Portland.

“It’s definitely different. It’s easier,” Grant told Yahoo Sports, “because they can’t load up as much, less help, less double-teams so, yeah, I mean, definitely easier. I will say that.

“Winning games and being able to do a bunch of things, be it on defense or offense, being able to contribute to my team, however that is, I’m willing to do.”

Grant is a piece the Trail Blazers of recent vintage didn’t have. It was Lillard, McCollum or bust — two small guards who could carry a team for stretches, but the rest of those rosters were thin.

Grant still gets after it defensively, quick and long enough to get after the guards but strong enough in his base to handle the 3s and 4s. The West doesn’t feel as impossible to break through as it did a few years ago, and having someone with Grant’s profile is a must.

Grant agrees that Billups coaches the team hard, and it’s necessary.

“He’s very precise. He knows what he wants,” Grant said. “He knows how to win. It’s perfect. You know it’s coming from a good place. I love it. … We have a bunch of underdogs here. It’s how we got off to a good start. Now we gotta make a few adjustments [to stay ahead].”

Lillard sees what the Celtics did last season as a blueprint: A few high-level scorers who committed themselves to the defensive end, caught fire after a shaky start and rode that to a Finals berth.

“Obviously, it’s different, but I have thought that to myself,” Lillard said. “They weren’t bad at the beginning of the season but eventually figured it out. They had two guys who could fill it up and wing depth. They were tough. They were coached hard. And because of that, they found themselves in position where you have a chance to win a championship.

“I see a similar thing for us.”

For Billups, his competitive fires are stoked when he's reminded of a play and counter Lue bested him on last season. Some weak-side action enabled Paul George to get an isolation on the right side, resulting in a jumper — followed by a review on Nurkic for a flagrant foul on Isaiah Hartenstein.

During the timeout, Lue ran the same action to free George but had Hartenstein slip to the basket, seeing that he was wide open on the previous play.

The Clippers ran the play to perfection, getting Hartenstein a dunk instead of the wing look to George.

Billups bangs the table playfully in remembrance, saying, “I’m gonna get him back for that,” with a wide grin.

Lue was right: Billups was made to coach.