The fact that Damian Lillard showed up as the Portland Trail Blazers' representative at Tuesday night's NBA Draft Lottery in Chicago tells you just how important this night was for the franchise. Well, hopefully he can at least expense the mileage for the trip.
After a disappointing start to the 2021-22 season, coupled by abdominal surgery for Lillard, the Blazers decided to tank in ways previously unfathomed by the sports world. Boasting a lineup chocked full of fringe NBA players and G Leaguers, Portland went just 2-21 after the All-Star break -- yes, they won TWO games in almost two months -- in an effort to land a lofty draft pick to use on a promising prospect or to sweeten a potential deal for win-now help.
The Blazers entered the lottery with the sixth-worst record in the NBA, and thus the sixth-best odds of landing the No. 1 overall pick. Lillard presented himself as all-business in an interview during the broadcast, then sat uncomfortably in a patterned collared shirt as the order was revealed. When the time for the seventh selection came, however, NBA deputy commissioner Mark Tatum uttered the dreadful words that Lillard and the city of Portland didn't want to hear.
"The seventh pick in the NBA Draft belongs to ... the Portland Trail Blazers."
Not only did the Blazers fail to jump into the top four -- they actually dropped a spot. If a picture's worth a thousand words, this video is a 200,000-word edition of "Moby Dick."
Damian Lillard’s reaction to the Trail Blazers falling to 7th in the #NBADraftLottery pic.twitter.com/KDy5Z9Z4qM
— Aaron J. Fentress (@AaronJFentress) May 18, 2022
Lillard's initial disappointment eventually turned to laughter, and what else can he do but laugh? Despite rampant speculation about a potential trade request following a sourced report from Yahoo's Chris Haynes last summer, Lillard has remained consistent in his message that he wants to remain in Portland. But that always comes with a caveat: Winning.
"I don't think we're in a situation where it's like, we have to win the championship next year, or it's a failure, but we just need to position ourselves to compete for the championship and also to where we can continue to build in that direction," Lillard told Haynes in March. "I think this is definitely critical, [a] critical summer where we have to capitalize."
Lillard was having a subpar year before surgery sidelined him, but he's still in the prime of his career, earning All-NBA honors in five of the previous six seasons. He'll be 32 when next season begins, however, and he knows the clock is ticking on his chance to be the best player on a championship team. As of now, the most exciting teammate Lillard has with the Blazers is emerging guard Anfernee Simons, who is a restricted free agent this summer. Outside of Simons, there are a whole lot of question marks.
In the same interview with Yahoo Sports in March, Lillard said he felt the Blazers had "taken some steps back as an organization" amid changes to the coaching staff and front office, along with a trade that sent his longtime running mate CJ McCollum to the New Orleans Pelicans. He remained optimistic, however, that the team's offseason flexibility would allow the Blazers to get back into contention.
Since then, things have gotten less optimistic. First, a late-season surge by the Pelicans -- ironically thanks in large part to McCollum -- caused the Blazers to lose out on New Orleans' 2022 first-round pick, which was considered to be a key piece of the trade. Portland would have received the pick if it fell within the 5-14 range, but by virtue of winning two play-in games, the Pelicans earned the No. 15 pick in the draft, which means it conveyed to the Charlotte Hornets rather than the Blazers.
Instead, the Blazers now receive a much less valuable 2025 top-four protected first-rounder from the Milwaukee Bucks, who are likely still going to be one of the best teams in the league at that time. And the No. 7 pick in this year's draft is just outside the range of players considered to be potential franchise-changers. The seventh-best player on the Big Board of CBS Sports NBA Draft expert Kyle Boone is Duke freshman AJ Griffin -- an intriguing prospect, but likely not one that will leave potential trade partners salivating.
The Blazers also have cap space, but -- assuming they're not in the mix for James Harden or Zach LaVine -- the free-agent market isn't exactly rife with superstars ready to take Portland back to the Western Conference finals. They could potentially throw a max offer sheet at a restricted free agent like Deandre Ayton, but teams will have the ability to match it.
All told, the pathway back to relevance is unclear for the Blazers, and Tuesday night's lottery only made things murkier. The speculation about a Lillard trade demand will undoubtedly continue as the offseason draws near, but it's also possible that he won't have to take that step. If the Blazers see the writing on the wall, they could preemptively trade their superstar point guard and kick off a full-scale rebuild. There are plenty of contenders (and the superstars who play for them) who would happily trade for Lillard, and the Blazers will likely fetch a better haul if they don't wait until a trade demand crushes any leverage they might have.
"If they came to me and they wanted to trade me -- I'm not going to fight them on wanting to trade me," Lillard told CNBC in April. "I don't want to be anywhere I'm not wanted. But I don't think that's the case."