LAS VEGAS — Damian Lillard was smiling. Why wouldn’t it be? The NBA offseason was less than two weeks away and already Lillard had come out on top. Last week, from a podium inside the Thomas & Mack Center, Lillard, flanked by Portland general manager Joe Cronin and coach Chauncey Billups, officially announced his two-year contract extension. The deal — which would add $122 million to Lillard’s contract, bringing his total remaining value to $258 million and securing the All-NBA guard more than $450 million in career earnings — keeps Lillard tied to the Blazers throughout the 2026-27 season.
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Or does it?
Lillard is firm on his desire to win in Portland. “What’s missing in our league is character,” Lillard said at the press conference. “And the fight, the passion and the pride of not just the name on the back, but the name on the front.” There is no reason to doubt him. For years, fans and the media have speculated about Lillard’s future. He did not do it. Lillard stuck with the small-market Blazers, insisting only on a desire to see a winning team built around him.
But if Lillard wanted a trade, he could get one. If he asked, the Blazers, assuming Lillard was still playing at a high level, would oblige, likely to a destination of his choosing.
This is the reality of the NBA today: long-term contracts no longer make sense. (Teams, of course, also have the ability to move players at any time.)
Contracts, especially the length and type players want to sign, have been a hot topic in the NBA for years. In the early 2000s, the league and players’ union argued over the length of players’ contracts. The NBA wanted to cap them at four years, five if a player re-signed with their current team. The union wanted six and seven. They settled at five, six with the current team. In 2011, the NBA reduced the length to four and five.
In the decade since, the landscape has changed. Superstar players, appreciating the flexibility and power (read: roster influence) that comes with it, signed shorter contracts. LeBron James did it when he signed with the Cavaliers in 2014. Then he did it again. In 2016, Kevin Durant signed a one-year contract with the Warriors. He then signed two more — like James, Durant got second-year player options on each of his contracts — before leaving Golden State in 2019.
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The most important change is more recent: players sign long-term contracts… then inform their teams that they no longer want to play for them. In 2017, Kyrie Irving, fresh off a third straight Finals at Cleveland and with two years remaining on his contract, said he wanted to leave the Cavaliers. In 2020, James Harden, with two seasons remaining on his contract, asked to leave Houston. Eight games into the season, the Rockets traded him. Ben Simmons had four years left on his contract when he told the 76ers he wanted to move. Philadelphia traded him to Brooklyn before the trade deadline. Durant didn’t make a penny on the four-year, $198 million extension he signed last fall. Still, he’s made it clear he wants a Brooklyn trade — and the Nets should oblige.
KD still has four years left on his contract with the Nets.
Wendell Cruz/USA TODAY Sports
Players squeezing their way out of unwanted situations is a growing trend, and one that is expected to continue. In Washington, Bradley Beal signed a five-year, $251 million extension with the Wizards. “I want to win a championship and I want to do it here,” Beal said. Maybe. But if the Wizards don’t reach title contender level soon — and Washington, which hasn’t won a playoff series since 2017, is nowhere near the match — Beal has the power to fight his way through. Lillard’s dedication to Portland is genuine. But if the Blazers’ recent maneuverings don’t push them up the Western Conference standings — and Portland, like Washington, has more questions than answers — Lillard can approach management about a trade. And the Blazers would probably work with him on it.
At the Summer League, team and league officials recognize the challenge. “They are the owners,” a senior team official said. “They’re soft. They can’t stand being uncomfortable. Many have cited Philadelphia’s handling of the Simmons situation as a role model. The Sixers refused to trade Simmons, fined him and only moved him because the return (Harden) warranted the deal.” But how many GMs can do that? said another executive. “How many are as comfortable in that type of environment as Daryl [Morey] and have the ownership support to do so? »
The NBA is engaged with union officials on a new collective bargaining agreement — the league and players can opt out of the current deal in December — but there’s no obvious solution there. The league could push for stipulations on maximum offers. For example, a player signed on a max contract is not eligible to be traded during the first three years of it. But that may not have the support of team owners who want the flexibility to waive a contract. Additionally, some team officials do not see the issue as a problem worth addressing. Better to have the player and be able to get something back for him via trade, officials say, than to lose him for nothing.
The Durant situation will be the next test. Brooklyn has signed several teams on Durant. As Sports Illustrated reported, the asking price was high. If not, several rival team officials told SI they hope the Nets won’t just offload him. It would be a victory for the teams. And that could be a win for Brooklyn. In the NFL, Packers quarterback Aaron Rodgers requested a trade after the 2020 season. Green Bay declined. Rodgers reported. The Packers went 13–4 last season with Rodgers picking up a second consecutive MVP. Last March, Rodgers signed a contract extension that will keep him in Green Bay until his 40s. Different sport but the Nets, if they show determination, can hope for the same result.
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