Damian Lillard, Scoot Henderson and the circle of NBA life in small markets
You are the Portland Trail Blazers. Your star player, Damian Lillard, has stayed loyal to the grind of building an NBA title contender in a small market, only help never came, because you are the Portland Trail Blazers.
LaMarcus Aldridge left when unrestricted free agency opened an exit for the first time in 2015. You built as best you could around Lillard. You first developed C.J. McCollum and then Anfernee Simons as high-level (if incongruous) backcourt scoring partners. You acquired Jusuf Nurkić to man the center position. You cycled through every complementary wing you could find, a list that includes Jerami Grant, Matisse Thybulle, Josh Hart, Norman Powell, Robert Covington, Gary Trent Jr., Trevor Ariza and a 35-year-old Carmelo Anthony.
These are good players, good enough to help Lillard reach the 2019 Western Conference finals in a bracket that boasted arguably the greatest team in NBA history. Moves on the margins may have made you mildly better, but Kevin Durant never considered you in 2016. You had to overwhelm Evan Turner and Festus Ezeli just to lure them to Portland. There is little sense in creating salary cap space when you cannot draw stars, and every trade has to be made with the understanding the acquisition could jet at the first opportunity.
Take Jimmy Butler, for example. He was available from the Minnesota Timberwolves in 2018, but that would have required trading McCollum with no assurance Butler would re-sign in Portland the following summer. Maybe one season of Lillard and Butler would have been worth it. More likely, Butler still forces his way to Miami, and you have downshifted from McCollum to Hassan Whiteside or Josh Richardson inside of a year.
Now, 11 seasons into his quest for a championship, a 32-year-old Lillard wants off your team and onto Butler's Heat in a deal that only makes it harder for you to build a winner in a bottom-10 media market. He wants what he once refused, joining other stars in a glamour market, because the system wore him down.
This has been the circle of life for teams in Minnesota, Orlando, Sacramento, Charlotte, Indiana, Utah, Oklahoma City, New Orleans and Memphis, among others, for their entire existence. It could hit Portland especially hard, since Lillard's request comes at the empowerment era's endgame, when a player with four years and $216 million left on his contract can name his next team, just before a new collective bargaining agreement designed to combat similar freedom of movement makes every front office's life more difficult.
The Pelicans are on their third trip around this circle since the league expanded in 2002. They drafted Chris Paul in 2005 and rode his success until his refusal to re-sign in New Orleans forced his trade in 2011, a year ahead of his unrestricted free agency. The Pelicans drafted Anthony Davis in 2012 and rode the same loop until 2019, when they dealt him to the only team he would re-sign with in his forthcoming free agency. That same year, they drafted Zion Williamson, who is now four years from entering the final year of his contract.
The cycle was so common that you could set your clocks to when a star might seek a trade from his small market to a glamour city. There is even a name for it: pre-agency. This can go one of many ways and most lead to Los Angeles. Only one — the highest-risk road for a non-destination — has led to a championship.
The Lakers and Clippers balked at emptying their caches of assets to acquire a then-injured Kawhi Leonard in 2018, knowing they had an inside line on recruiting him in free agency a year later, when everyone would know more about a chronic injury to his right quadriceps. Meanwhile, the Toronto Raptors stepped up with an offer of DeMar DeRozan, Jakob Poeltl and a top-20 protected first-round draft pick. Toronto is a large market but operates somewhat like a small one in Canada, where they have paid the luxury tax once since 2004 — for the 2018-19 season, when Leonard led the Raptors to their only title before bolting for LA.
Risk won them a ring. Any number of factors could have left us looking back at the trade for Leonard and the four years since his free-agency exit — one playoff series victory and two lottery appearances — in a different light. Leonard appeared in every playoff game for the Raptors, something he has done only one other time since 2016. His Game 7 buzzer-beater in the Eastern Conference semifinals bounced four times before finding the bottom of the basket. Both Durant and Klay Thompson suffered series-ending injuries in the 2019 NBA Finals against Toronto. Everything had to fall right for Toronto, and it did.
The Thunder's attempt to thread that same needle backfired. After trading future MVP James Harden to cut costs in 2012 and losing Durant to free agency in 2016, they took a swing on Paul George in 2017, trading future All-Stars Victor Oladipo and Domantas Sabonis to the Indiana Pacers, knowing George preferred to play in Los Angeles. Oklahoma City even signed George to a maximum contract extension a year later, believing the gamble paid off, only to lose him to his trade request to join Leonard on the Clippers in 2019.
Maybe this is just the natural order of the NBA. Either the trade works, or it doesn't. Your star is good enough to carry you to a championship, or he isn't. Giannis Antetokounmpo and Nikola Jokić led the smaller-market Milwaukee Bucks and Denver Nuggets to titles in two of the last three years. Lillard is not on their level, and that is NBA life. Except, the natural order makes NBA life a little easier in destination cities, where you do not need a winning lottery ticket to manufacture a ring. You need only perpetual sunshine.
The Lakers pulled a title from years of mismanagement, simply because LeBron James wanted to live in Los Angeles, and his agent persuaded Davis to join him. The Heat rebounded from a downturn because Butler wanted to play in Miami, and the Philadelphia 76ers inexplicably obliged him. This does not happen for a team like the Blazers, who cannot attract stars and cannot get equal value when theirs want to leave.
At least small-market teams were being rewarded when the empowerment era was in full swing. OKC received Shai Gilgeous-Alexander, Danilo Gallinari, five first-round draft picks (four unprotected) and two pick swaps in exchange for George. The Thunder had leverage, knowing Leonard threatened to join the Lakers if the Clippers did not land George. Why the Lakers traded so much for Davis — Brandon Ingram, Lonzo Ball, Hart, three first-round picks and a swap — is beyond me, since his agent (like Lillard's) made it clear he wanted to play for only one team, but the Pelicans got a jump-start on their next rebuilding cycle.
Small-market teams reacted by trading stars before all leverage was removed. The San Antonio Spurs dealt Dejounte Murray with two years left on his deal, and the Utah Jazz jettisoned Donovan Mitchell with three years remaining on his, understanding the return would soon diminish the closer they came to free agency.
Team owners also snuck a poison pill into the new CBA, severely restricting a star's ability to both get his max contract and choose his next destination. Starting next summer, teams over the second apron (half the league is committed to spending more than the current figure of $179.5 million) must send out 100% of incoming salaries but cannot aggregate outgoing contracts or sign-and-trade an outgoing player to do so.
In other words, the Heat may not be able to acquire Lillard a year from now, so we are seeing a rush of stars push for trades to a sole destination. Everyone understands the stakes, save for anyone who assumes this Lillard precedent — requesting a trade to the team of his choice with four years remaining on his contract — is the next stage of the empowerment era and not the last gasp of it. Teams are especially aware of this.
In exchange for Bradley Beal, the Washington Wizards — another large market that operates like a small one (a concerning trend for players) — accepted what amounted to Jordan Poole, Landry Shamet, a top-20 protected first-round pick, four swaps and seven second-round picks. Beal owned a no-trade clause, and the Wizards wanted off his contract, which includes a $57.1 million player option for the 2026-27 season.
The Blazers are not just trying to shed Lillard's salary, just like the Sixers do not want to deal Harden in exchange for whatever the Clippers can cobble together. They want maximum value — the sort of deal the Pelicans and Thunder respectively received for Davis and George — except Miami and LA are taking advantage of this last gasp before the highly restrictive new CBA. Who else will part with significant assets for a well-paid 33-year-old at this juncture and when else will any title contender be able to trade for him?
If Lillard does not change Miami's championship fortunes, they could be paying him $58.5 million at age 35 with no recourse but to wait until his contract expires in 2027. There is risk in that, too, and for all its faults, the new CBA may have gotten something right by making life harder for everyone, not just smaller markets.
It is unfortunate timing for the Blazers, and they will probably be forced to accept a few first-round draft picks, maybe some swaps and whatever they can get from a third team for Tyler Herro in exchange for Lillard. That is easier to swallow with Scoot Henderson. The hope is that Henderson rises to the level of Jokić or Antetokounmpo, and the CBA levels the playing field for you to build a better roster around him.
You are the Portland Trail Blazers, and your NBA circle of life is beginning anew, only the future is brighter.