The Trail Blazers had every opportunity to blow it up and begin a rebuild. Instead, they opted to retool around star Damian Lillard. Boardroom explores the path it took to get here.
The Portland Trail Blazers are the only remaining undefeated team in the Western Conference at 4-0 entering Wednesday, with wins over the Phoenix Suns, Los Angeles Lakers, and Denver Nuggets. It’s the first time they’ve started the season with such a record since the 1999-2000 season.
After a disappointing 27-55 season in 2021-22, in which Damian Lillard missed 53 games, the team was seemingly stuck in a weird state of limbo. But after Lillard agreed to a two-year extension through the 2026-27 season in early July, it was clear the Trail Blazers had undergone an extraordinary, unique, and quick rebuild — if that’s what you want to call it.
They have a long way to go before they’re considered championship contenders, but things are lining up in more ways than one — from the front office, coaching staff, and down to the product on the court.
Make no mistake: Dame’s loyalty is unprecedented. He could’ve ditched this whole debacle to ring chase. He IS the main reason any of this is possible.
So, while teams continue to rebuild through years of tanking, Portland spent $146 million (18th-most in the NBA) to produce the seventh-youngest team (24.4 years old) in the league. It’d be awfully hard to replicate.
Boardroom takes a look at how they got here.
Step 1: Hire Chauncey Billups
The one-time NBA champ landed his first head-coaching gig when he was hired by the Trail Blazers in July 2021. He was integral in getting through to Dame, using his own playing days to relate with the human versus the player.
“I told Dame this before I got the job: ‘I ain’t recruiting you.’ I’m going to tell you what I feel and what I think because I care about the person,” Billups said in an interview with The Ringer. “You got decisions you have to make for you and your own family.”
This helped Dame commit to the organization with the right guy at the helm.
“That’s why I fuck with him so heavy. He knows the game, he’s a thinker, he’s a players’ coach, he has relationships with everybody, but I know he’s going to keep it solid,” Lillard said.
Step 2: Get Olshey Out
It’s awfully difficult to recover when the president of basketball operations is under investigation for workplace misconduct — especially when you’re trying to convince the franchise player to stay. The team fired Neil Olshey on Dec. 3, 2021, and replaced him with Joe Cronin, who joined the team as a basketball operations intern in 2006.
Cronin got to work immediately.
Step 3: Trade CJ
Tough pill to swallow, but trading co-star and fan favorite CJ McCollum created roughly $60 million in cap space ($16 million under the luxury tax) this past summer, and $21 million in trade exceptions.
Additionally, they brought in a bunch of role players from New Orleans who they later dumped. They retained Josh Hart and Didi Louzada, and received a 2025 first-round pick.
The Dame-CJ duo led Portland to eight straight postseasons while playing 60% of the team’s games in six seasons — the second-most for any duo in history.
Step 4: Make Moves
If the Trail Blazers were going to convince Dame they could put together a winning product, they’d have to make appropriate trades and put the right players next to him. By moving McCollum, they remained flexible in regard to trades and free agents. Take a look:
- June 22, 2022: Traded Gabriele Procida (No. 36 pick in the 2022 draft), the 2025 pick they acquired in the CJ trade, and two second-rounders for Detroit star forward Jerami Grant. He’s averaging 17 points thus far.
- July 6, 2022: Portland extended Anfernee Simons to the tune of four years, $100 million. Simons, 23, was drafted by Portland in 2018 and slid right into McCollum’s spot. He’s averaging 19.8 points through the first four games.
- July 6, 2022: The team re-signed big man Jusuf Nurkic on a four-year, $70 million deal. The center from Bosnia is a walking double-double, now in his seventh year with the Blazers. He’s averaging 11.8 points and 12.3 rebounds.
Step 5: Pay Dame
No wonder the interim tag for Cronin was lifted in May. He may not have hired Billups, but he managed to create space, acquire Hart and Grant, and retain Portland’s remaining stars — all while maintaining a level of financial flexibility.
That was enough for Dame to stay. On July 8, Lillard agreed to a two-year, $122 million extension to stay through the 2026-27 season — earning roughly $137 million over the next three seasons before the extension kicks in. His $44,066,288 average annual salary is the sixth-highest in the NBA.
Will this team win a championship? Probably not. FanDuel Sportsbook has Portland at +13000 to win it all, the 20th-best odds in the NBA.
But the Trail Blazers are young, fun, exciting, and most importantly — they’re good.
Lillard and Simons have quickly emerged as one of the most compelling backcourt duos in the West, while Grant and Nurkic hold down the frontcourt.
It’s hard to dive deep into numbers only four games into the season, but perhaps more teams should take a page out of Portland’s playbook. The team could’ve easily folded and given up its superstar like many teams have done before, prepared for a rebuild, and potentially stunk for the next 5-10 years.
Instead, the Trail Blazers boast a good blend of star power and young players for a win-now team.
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