The Portland Trail Blazers exited last year's Orlando bubble ever-bullish on their trio of Damian Lillard, CJ McCollum and Jusuf Nurkic. Gary Trent Jr.'s strong playoff run also previewed a player who could perhaps provide the Blazers' long-missing piece on the perimeter.
To keep pace in a loaded Western Conference, Portland's top priority this past offseason became adding more defensive wing depth. Building the ideal roster around the already strong core is especially important for the Blazers as the clock starts to tick louder on Lillard's prime.
President Neil Oshley even lobbied Lillard to provide a list of potential complementary stars, league sources told Bleacher Report. Lillard spent considerable time assessing rosters across the league. It is known that Aaron Gordon was one of the considered additions, though it appears Portland chose to pursue Robert Covington at the time instead.
The Blazers' task is strikingly similar to the Warriors optimizing these final years of Stephen Curry's union with Klay Thompson and Draymond Green, as both Curry and Lillard now stand north of 30 years old. Green, sources said, is also the premier malleable defender Portland has long dreamed of supporting its Lillard-McCollum tandem.
To be clear, that does not mean Portland needs to supplement Lillard with another star to keep him. By all accounts, the Blazers centerpiece is perhaps the most loyal of NBA stars, hailed around the league as a rare breed of culture setter. He has long rebuffed recruiting attempts from rivals—and there have been plenty. In this league, LeBron James drafting Lillard to three straight All-Star squads is not coincidence.
Lillard's unwavering allegiance has allowed the Blazers to confidently, and uncharacteristically, splurge for upgrades on the wing, first dealing two first-round picks for Robert Covington and then recently swapping Trent for Norman Powell before the trade deadline. The Blazers hope those additions, mixed with Lillard's locker room presence, can all blend along the point guard's timeline.
Now, will it all be worth the front office gambling more chips than they've typically been willing to trade?
"Neil loves the draft," one longtime Western Conference executive said of the Blazers president. "To give up two draft opportunities to get Robert Covington, it's not a norm for him. It's a norm for Daryl Morey, but that's a move Neil doesn't normally do."
"Those are both win-now moves," said another league personnel man, also referring to moving Trent in favor of Powell.
The Blazers had been engaged in conversations with Orlando regarding Gordon for several years, yet Portland was never willing to include Anfernee Simons in any outgoing package, sources said.
It's believed that Magic president Jeff Weltman also preferred Denver's R.J. Hampton over Simons as a young blue-chip prospect. Even leading up to the draft, league executives speculated Hampton's range started at No. 15, where Orlando ultimately took Cole Anthony.
Surrendering that pricey of a package for Gordon may have been too rich for the Blazers anyway, although it does seem Lillard valued Gordon—another Bay Area native, whose parents now reside in Portland—more than Olshey's front office did. The Blazers have always preferred to operate more frugally, slipping into creative three-team deals, like how they netted both Enes Kanter and Hassan Whiteside.
But it does appear that Portland's ownership has signaled a willingness to support what will become a very expensive roster for 2021-22. Lillard's still-rising salary will catapult to over $40 million in the first season of a four-year deal worth over $200 million, while McCollum is also on the books for north of $30 million through 2023-24.
"When two players cobble together 60 percent of the cap, it's hard to build a team around them unless you're Brooklyn or Golden State, where the owners are willing to pay a big tax dollar," said one assistant general manager.
Zach Collins presents an interesting restricted free agency case study since he's played only 11 games over the past two seasons. His name was discussed in those Gordon trade talks, sources said, but Portland has long messaged a strong belief in the 23-year-old's upside.
Portland will almost surely become a perennial taxpayer, especially if it can retain Powell this offseason.
The Blazers, of course, have every incentive to retain their newly acquired wing. They sacrificed the right to match any of Trent's offer sheets in restricted free agency, betting that their on-court success and Lillard-driven locker room will urge Powell to stay put even as an unrestricted free agent.
"Knowing what Portland gave up and how many suitors there were, I think he's the most interesting guy on the market," said another Western Conference team official.
The success of this latest iteration of the Blazers' experiment will undoubtedly set the tone for how Powell moves forward. Over a dozen teams maintained a dialogue with Toronto up until the final hours before the trade deadline, league sources said. (Brooklyn was discussing a deal centered on Spencer Dinwiddie all of that week. The Pistons were also in strong pursuit, and the Pacers, Timberwolves, Rockets and Knicks were among the teams closely monitoring Powell's availability as well.)
It seems such widespread interest scared off many teams from bidding too aggressively for Powell. That naturally forecasts what could be a very competitive landscape for Powell's services next season and beyond.
Part of the Blazers' calculus in swapping Trent for Powell was projecting their former second-round pick's next salary to average around $15 million annually, only for Trent to largely play backup minutes to McCollum. Powell's number is expected to be around $20 million, according to league sources polled by B/R, yet he's played as the Blazers' third starting guard, capable of defending opposing small forwards.
But what if some team with cap space, perhaps the New York Knicks, were to extend a significantly higher offer? "The Powell numbers might get crazy," said one Western Conference voice. Tom Thibodeau has long been considered to covet Powell, and the Knicks could offer him a four-year agreement north of $100 million if they choose.
"As the saying goes, it only takes one assh--e," said one team cap expert.
If Powell does stay, that creates another potential pivot point for Portland's Lillard-centered project. Perhaps Powell finally provides the insurance and flexibility for the Blazers to explore moving McCollum for a player who's a better fit for Lillard's second act.
That's getting a bit ahead of ourselves. But that's why the Powell addition may be as interesting as any in the league, this side of the Nuggets making their own move to add Gordon. The Blazers are holding onto a top-six playoff seed all while injuries have clearly prevented Terry Stotts' roster from throwing its strongest punch.
Lillard, McCollum and Nurkic have only appeared in 18 games and played 332 total minutes together, per NBA.com. Lillard, Covington and Derrick Jones Jr., by comparison, have logged 772.
If Portland can stay healthy, the question becomes whether a refortified rotation can boost the Blazers from Western Conference irritant to bona fide contender.
"I feel like they're always the same team," said another assistant general manager. "They can lose in the first round or they can get lucky or hot and make the conference finals."
Should these latest moves change that perception and introduce a greater ceiling for Portland's reality, maybe Lillard's title window opens wider—before it inevitably slams shut.
Jake Fischer covers the NBA for Bleacher Report and is the author of Built to Lose: How the NBA's Tanking Era Changed the League Forever.