Lowe: Why the Damian Lillard-Blazers breakup actually began eight years ago

In 11 seasons in Portland, Damian Lillard averaged 25 points, 7 assists and 4.2 rebounds per game. The Blazers made the playoffs in eight of those seasons, but advanced to the conference finals just once -- in 2018-2019. Sam Forencich/NBAE via Getty Images

NO TEAM ARRIVES at the crossroads the Portland Trail Blazers face now because of a single recent decision -- in this case Portland using the No. 3 pick on Scoot Henderson instead of trading the pick to appease Damian Lillard.

The Blazers' front office was sincere in its belief it could straddle two paths -- take Henderson, and work trades and free agency to build a competitive team around Lillard. It would be hard, and require luck. For Lillard, the odds of success were too long. That was a fair conclusion, too.

I have not heard convincing evidence that a sensible deal exchanging the No. 3 pick (and another player, likely Anfernee Simons) ever materialized for Portland. Moving up in the lottery -- jumping from No. 5 to No. 3 -- changed everything. For most talent evaluators, Henderson is better than the typical No. 3 pick -- maybe much better.

Trading a prospect that valuable for a veteran is a weighty decision. It has to be the right veteran -- available, reliable, good enough to put you into the inner circle of title contention, hopefully not so old you have completely knee-capped your future.

The Brooklyn Nets never showed interest in swapping Mikal Bridges for that Simons/No. 3 package, sources said; it's unclear if the teams discussed it. The Miami Heat chuckled at Portland potentially asking about Bam Adebayo.

The LA Clippers would push back on the notion that they genuinely explored Paul George's trade value, but if they had, you cannot flip Henderson for a 33-year-old who hasn't played in more than 56 games since 2018-19 -- let alone one eligible for a massive extension.

The New Orleans Pelicans and Toronto Raptors weren't ready on draft day to pivot away from Zion Williamson, Pascal Siakam, or O.G. Anunoby, sources have said. Williamson is a franchise-changer when healthy, but he's rarely healthy. Siakam and Anunoby are very good -- Siakam is an All-Star -- but would either have vaulted Portland into the ring of championship favorites?

In a strange way, you can trace the seeds of Lillard's departure all the way back to an opportunistic trade from eight years ago: the Blazers acquisition at the Feb. 2015 trade deadline of Arron Afflalo from the Denver Nuggets in exchange for Will Barton and a lottery-protected 2016 first-round pick. It was a sound move made with an eye on both the present and the future -- but almost nothing after that day unfolded quite as planned.

THE BLAZERS WERE 36-17, tied for third in the West, merging into the kind of improbable maybe-contender Portland's current brass probably dreamed of building around Lillard now. They were constructed around a tentpole star in LaMarcus Aldridge; a home-run draft pick (Lillard) swiped in a laughable heist of a trade with Brooklyn; and savvy under-the-radar acquisitions from the back of the first round (Nicolas Batum), restricted free agency (Wesley Matthews) and minor trades (Robin Lopez.)

Aldridge was set to enter unrestricted free agency after the season. The Blazers had to go for it. They needed depth, and so then-GM Neil Olshey, dipped into the team's future to add Afflalo. The pick they gave up was lottery-protected in 2016, meaning that if Aldridge left and the Blazers bottomed out, they would keep it.

It was the sort of small trade that would come to define the next eight years -- smart (not all were smart), but not enough to catch the big boys or in later years address the structural limitations of a team constructed around two small guards: Lillard and CJ McCollum.

Two weeks later, Matthews tore his Achilles. The team faded and lost 4-1 in the first round.

The Blazers appeared to know Aldridge had eyes for the San Antonio Spurs. Ahead of the draft, Olshey dealt Batum to the Charlotte Hornets for Noah Vonleh -- the No. 9 pick in the 2014 draft. (The Blazers also got Gerald Henderson.) Batum was about to enter the final year of his contract -- with a big new deal coming. The trade was largely praised.

Ten days later, Aldridge left. Matthews bolted for the Dallas Mavericks. The Blazers appeared to be entering a quick-turn rebuild, with the potential of nabbing a high draft pick in 2016 that could propel the franchise forward with Lillard as the centerpiece.

Plot twist: The 2015-16 Blazers were a playoff team. Lillard eased into an undisputed No. 1 option role. They got strong play from one forward they snagged in free agency (Al-Farouq Aminu) and another they stole from the Orlando Magic (Maurice Harkless) -- good moves. They flipped their 2015 first-round pick (Rondae Hollis-Jefferson) to Brooklyn for Mason Plumlee -- a serviceable center.

Two years later, they traded Plumlee to the Denver Nuggets for Jusuf Nurkic and a first-round pick -- another reminder Portland did some smart things on the edges, but that smart moves on the edges often don't amount to enough if the bigger move never comes (or if bad fringe moves undo some good work).

McCollum in 2015-16 won Most Improved Player. He was a great pick at No. 10 in 2013 -- the last time the Blazers had a chance to pick high until Shaedon Sharpe last year. (The Blazers also had the No. 11 pick in 2012 -- the year they drafted Lillard -- and selected Meyers Leonard.) Definitional to the Lillard-Blazers story is that by far Portland's best draft pick between Lillard and Anfernee Simons was another ball-dominant guard almost exactly Lillard's size.

The 2015-16 Blazers won 44 games and a playoff series despite Aldridge's defection. Instead of picking at the top of the 2016 draft, they lost their pick outright via the Afflalo trade.

That summer, they faced a fork in the road: maintain flexibility, or use their cap room while retaining several key players. Olshey concluded that opening meaningful room in future summers would require letting too many players walk for nothing and delaying McCollum's extension. He knew Portland had no history of luring major free agents.

So, the Blazers spent. They retained Harkless, Leonard and Allen Crabbe on contracts totaling almost $160 million. (They matched a Nets offer sheet on Crabbe.) After striking out on higher-profile targets -- including Hassan Whiteside, sources said then -- Portland used room on a four-year, $70 million deal for Evan Turner.

EVERY DEAL WENT bust. It was clear almost right away the Blazers would have been better off looking for bargains that might have turned into trade assets; using room as a dumping ground; or inking shorter deals to keep room open beyond 2017. It's not a great sign when your head coach (Terry Stotts then) predicts mere weeks after free agency, "We are probably not going to make the quantum leap the salaries might indicate."

Portland back-slid to .500 in 2016-17, and got smashed in the first round by the Golden State Warriors. No matter: Portland had three first-round picks in the coming draft.

They traded two -- Nos. 15 and 20 -- to move up five spots for Zach Collins. Donovan Mitchell and Adebayo were selected at Nos. 13 and 14. With their own pick -- No. 26 -- the Blazers selected Caleb Swanigan; Josh Hart, Derrick White, and Kyle Kuzma comprised three of the next four picks.

If you had to boil down Portland's challenges building around Lillard to two moments, you may land on that 2016 spending spree and draft night 2017. After that, the Blazers spun their wheels with incremental deals for wings, tweener forwards and second-third big men. They never appear to have gotten deep in talks for deals that would have exchanged several picks and players for a co-star who was a cleaner fit alongside Lillard.

Perhaps they suffered a sort of paralysis by paranoia -- a founder's loyalty toward McCollum, combined with fear that any outside star would leave.

On that same 2017 draft night, the Indiana Pacers were taking offers on Paul George -- entering the final year of his contract. Portland checked in that night, offering multiple picks and at least one player for George, sources told ESPN then, but the Train Blazers never appeared to have gotten into the real negotiating.

The holdover core got the Blazers pretty far -- two straight playoff appearances, including a conference finals run in 2019. Skeptics dismiss that appearance. The bracket broke right for Portland, and they eventually got swept by Golden State.

But making the conference finals is hard. There have been lots of teams that failed to take advantage when the brackets broke right. (Ask any Philadelphia 76ers fan.) Jusuf Nurkic missed the entire 2019 postseason. The Blazers were very good, but short of championship-level. No shame in that.

THEY HAVE NOT won a playoff series since. In that time, they made a slew of half-measure-style win-now moves. The splashiest was trading two first-round picks for Robert Covington in 2020 -- a move that was almost universally lauded. The cost was high, but Covington was probably the best Portland could do at that price point -- the rangy 3-and-D wing/power forward the team had craved since Lillard's arrival.

Later that season, they flipped Gary Trent Jr. -- a fantastic draft-day catch in 2018 -- for Norman Powell. Again, the reaction leaned positive. Powell added a downhill attacking gear Portland needed.

That gave Portland what looked on paper to be its best starting five since that 2014-15 season: Lillard, McCollum, Powell, Covington, and Nurkic. It was small, but profiled as explosive on offense and maybe above-average on defense - provided elite play from Covington and Nurkic.

It didn't work. The group flamed out in the 2021 playoffs, losing a dispiriting first-round series to an injury-ravaged Denver team. The Blazers fired Stotts. Portland traded another first-round pick for Larry Nance Jr. -- a good third big man who was expected to close some games as a small-ball center. The pick was heavily protected through 2027, limiting Portland's ability to toss more picks into win-now trades.

The team sputtered. Olshey was fired amid an investigation into the Blazers' workplace. His replacement, current GM Joe Cronin, traded Powell and Covington to the Clippers, receiving almost nothing back.

Cronin finally broke up the McCollum-Lillard duo, trading McCollum and Nance to the Pelicans for a package centered around Josh Hart. A year later, Portland traded Hart to the New York Knicks for what became the No. 23 pick - Kris Murray. (Portland expanded the deal to acquire Matisse Thybulle from the Sixers.)

That cascade from McCollum to Murray does not get as much attention in explaining Lillard's alienation as the decision to draft Henderson - and the decision last year to pick Sharpe at No. 7 instead of trading the pick, a move that again may not have been realistically available - but it may be grounds for the most piercing critique.

Portland waited too long to seriously explore McCollum deals, and ended up selling low -- and then traded away a valuable veteran wing in Hart.

WHAT SUPERSTAR TRADE discussions might Portland have butted into had it tried years earlier to package McCollum with a boatload of picks and swaps? What about player-for-player deals that would have reoriented the team and left their stockpile of picks intact? Portland brass never showed much interest in NBA Twitter's favorite fake trade of McCollum to the Orlando Magic for Aaron Gordon, sources have said. That deal alone would not have transformed Portland into a contender, but it would have given them a new dynamic and a roadmap to build a different kind of team.

It is fair to ask which stars the Blazers should have chased. Smaller guards -- Kyrie Irving, Dejounte Murray, Bradley Beal, Donovan Mitchell, Zach LaVine -- would have duplicated the Lillard-McCollum fit issues. James Harden is bigger than those guys, but not the best fit.

Disgruntled superstars with only one or two years left on their contracts were perceived as instant flight risks. That was understandable, particularly with superstars who signaled their desire -- as Lillard is now doing with Miami -- to go to one team; the Blazers were never going to outbid the Los Angeles Lakers for Anthony Davis, as one example.

Should they have been bolder chasing big wings who came onto the trade market with minimal time left on their contracts: George, Jimmy Butler, Kawhi Leonard? Leonard and Butler changed teams before and during the 2018-19 season, and became defining figures of those playoffs -- with Leonard's Toronto Raptors winning the title. Both moved again that offseason, leaving their former teams with little or nothing in return.

Philly and Toronto acquired Butler and Leonard, respectively, for prices so low as to be almost risk-free. Would McCollum have satisfied Gregg Popovich's desire for a veteran in the Leonard trade -- something Toronto supplied with DeMar DeRozan? Hard to say. Leonard almost certainly would not have stayed in Portland, and trading real assets for a rental that falls short of a title hurts.

But openness and creativity unlock more possibilities. The Blazers didn't operate with enough of those traits. There were good and real reasons behind their caution, and they hit on several smaller decisions. But they didn't hit enough, and none of them really changed their team. Trading what could be a low first-round pick last summer for Jerami Grant -- another good valuable proposition -- proved too little, too late.

Now they are here, hoping to dredge up a better deal than what Miami can offer -- or at least convince the Heat they have to offer everything. That is Portland's right, just as it is Lillard's right to try to get where he wants. The process could be long and unpleasant. That is the trade-off Lillard made when he signed a massive extension with Portland last July: He may well end up in Miami, but he can't dictate the timeline or the tenor of the process.

Miami could offer Tyler Herro, Nikola Jovic, Jaime Jaquez Jr., and up to three unprotected first-round picks if they amend the terms of the pick they owe the Oklahoma City Thunder. That is a better offer than it has been made out to be, assuming the Blazers can spin Herro into at least one good first-round pick. Unprotected Miami picks in 2028 and 2030 -- and whatever swaps the Blazers might coax -- could be valuable given Lillard and Butler are in their 30s. It's not a great offer akin to what Brooklyn got for Kevin Durant and the Pelicans' return for Davis, but every situation is different. Lillard is a 6-2 guard who turns 33 on Saturday and is due a ton of money.

Other teams could beat that Miami offer -- if they want to risk it, or get word from Lillard he would come in with an open mind. Teams have to bet on themselves, too. (I went through theoretical Lillard trades last week on the Lowe Post podcast.) But Miami's offer is at least palatable.

It's fitting Portland and Miami are intersecting here. They are very different markets, and those differences have informed -- right or wrong -- how each franchise has operated. Both have been successful, but Lillard wants a team willing and able to act with an urgency that matches his urgency to win it all before it's too late.