Knicks, Immanuel Quickley fail to reach contract extension, so what happens now?

Immanuel Quickley’s future is uncertain.

The New York Knicks did not extend the 24-year-old before Monday’s 6 p.m. (ET) deadline, meaning Quickley will become a restricted free agent next summer. A season after establishing himself as the best player on the Knicks’ bench and finishing second in NBA Sixth Man of the Year voting, Quickley is betting on himself.

For much of the summer, there was optimism within the Knicks that the two sides could find a common ground. Starting July 1, first-round picks from the 2020 draft were eligible to sign extensions, which would kick in for 2024-25. Fourteen guys signed deals before Monday’s deadline.

The Knicks’ current front office has a history of giving out extensions. A couple of summers ago, it extended Julius Randle. In September 2022, RJ Barrett received one off his rookie-scale contract, the same type of deal Quickley was eligible for this summer. And this past August, Josh Hart added four years to his contract.

Quickley will not join the list. Questions about his future will linger for the rest of the season — and they won’t only be about his upcoming free agency.

The Knicks, on the constant hunt for a star, have operated under an assumption, according to league sources familiar with the situation: The most likely scenario is that an MVP-level game-changer won’t become available on the trade market until next summer. It’s one reason why they engaged in extension talks with Quickley. Because of a quirk in the NBA’s brutally complicated collective bargaining agreement, it is more difficult to trade a player who signed an extension off his rookie-scale deal in the season before the new contract kicks in — in this case, 2023-24. No player has ever signed a rookie-scale extension for an eight-figure salary and then been traded during the ensuing season.

If the Knicks had extended Quickley and a superstar became available next summer, they could have used the guard’s new, bigger salary to pair with another eight-figure one and bring in the faceless hero they’ve longed for since team president Leon Rose took over in 2020.

The Knicks hoped to lock up Quickley because it made the most sense for long-term roster building and that’s what you do with young players who have the potential to break out. But it never happened. The two sides were too far apart.

The Athletic conducted a poll earlier in the summer, asking 16 executives what they would deem a “fair” extension for Quickley. The most common responses ranged from $16 million to $20 million a year. But the climate has changed since then.

San Antonio Spurs wing Devin Vassell, a member of the same draft class as Quickley, signed a five-year, $135 million extension three weeks ago. Minnesota Timberwolves forward Jaden McDaniels inked a five-year, $136 million on Monday. Even if you approached the greatest Quickley optimist, someone who believed he was worth as much as Vassell or McDaniels (and asking around the league, I don’t think you’d find many of those people), it would have been difficult for the Knicks to justify such a price tag — if only because of Quickley’s role.

As long as Jalen Brunson is in town, Quickley is bound to come off the bench, and it’s difficult to fill out other positions of need with a starting small guard and his backup making as much as the two would after Brunson signs an inevitably more expensive contract down the line.

It’s not like Vassell’s and McDaniels’ contracts were the norm, either. Cole Anthony, an instant-offense guard who refined his game better during his third season, re-upped with the Orlando Magic for $39 million over three years, a deal that came together Monday. Josh Green, the Dallas Mavericks’ premier 3-and-D contributor, received $41 million over three years not long after.

Quickley’s market should fall between the Vassell and Green ranges. But we won’t know for sure what the league thinks of him until next summer.

And now, questions aren’t just natural. Without a crystal ball, they’re unanswerable.

Does Quickley go elsewhere in free agency next summer? Do the Knicks plan to match any offer for him and bring him back, which is their right since he is restricted? Could a sign-and-trade happen? Is his status in flux until the Feb. 8 trade deadline? If the Knicks and Quickley were far apart on money, does New York worry it would encounter the same issue in free agency and flip him at some point over the next four months?

If Quickley takes another leap, someone may make him a big offer next summer, putting the Knicks in a difficult position: stuck between paying him more than they want or watching one of their best players leave.

The Magic are young, talented, will have loads of cap space and could seek out a point guard who fits their timeline and would complement up-and-coming studs Paolo Banchero and Franz Wagner. The Utah Jazz will have room, could use a point guard and their president, Danny Ainge, has been a fan of Quickley’s dating back to the 2020 draft, when Ainge was running the Boston Celtics. The San Antonio Spurs will have space, both financially and on the roster, to add another guard. Who knows what happens with the Philadelphia 76ers, who could have cap room or not and already employ Quickley’s college teammate, Tyrese Maxey? Maybe the universe allows the two best unextended players from the 2020 draft class to reunite.

But Quickley getting paid is no guarantee. Make no mistake; him steering away from an extension is a risk.

What if he churns out another excellent October through April but struggles in the playoffs once again? That would mean he’s entering the opening market following two consecutive subpar postseasons, something front offices would surely bring up during negotiations.

Even if Quickley excels from start to finish, there’s no promise of a lucrative market. Restricted free agency is notoriously unkind. The Magic could fall in love with their core and wait on a bigger move. The Jazz have all the flexibility in the world with their cap space, as well as their stash of draft picks. Why should they rush to sign a career reserve? The Spurs could look elsewhere.

The new CBA, which the league and players association agreed to over the summer, will not be friendly to the middle class. Sign-and-trades won’t be as prominent, because new rules restrict teams who spend too much from making them. Salary-matching regulations are more stringent, too. And if all these factors submerge to suffocate Quickley’s market, a talented guard may have to return to New York on a contract that was less than the one he hoped for leading into this week.

It’s a wonder how Quickley feels about this. He’s brushed off the topic when asked about it in the past. Reporters requested to interview him following the Knicks’ practice Monday, but the team would not make him available.

Monday’s finale adds another chapter to the Knicks’ in-and-out relationship with their sixth man.

Around this time last year, New York was calling around the league, gauging other organizations’ opinions on Quickley, league sources told The Athletic at the time. The asking price was a first-round pick — though it’s not like the Knicks were trying to give him away for a highly-protected selection. It would have taken something juicy to get New York to bite. But by the middle of the season, when Quickley was in the midst of his best-ever run, the organization’s strategy changed. All of a sudden, the Knicks were clutching onto Quickley tightly. Come last season’s trade deadline, teams that once thought Quickley was gettable couldn’t even ask about him.

But now, after all the ups and downs, only hours after Knicks head coach Tom Thibodeau declared himself “a big Quickley guy” following Monday’s practice, there is another blip.

We should have known all summer that it would come down to the wire.

Not long after the Damian Lillard trade, as I called around the league asking for perspectives on the star’s move to Milwaukee, someone in the know told me the deal came together quickly. The Bucks called late in the summer. The Portland Trail Blazers completed a deal shortly after. And that was it.

An obvious question presented itself. If negotiations were so efficient, why did the Blazers not move Lillard, who requested a trade months before one went down until just days before the start of preseason?

“Deadlines, man,” the person told me on the phone.

I can only imagine a shrug accompanied the two-word response.

There’s a reason Portland finally agreed to a deal just in time for the season to begin. It’s the same reason trades often go down the week of the trade deadline and rarely happen at the end of January. It’s the same reason why no one turns in the essay that’s due Friday on Wednesday or why of the 14 rookie-scale extensions that got done this offseason, eight of them happened within 24 hours of the deadline.

The NBA is full of procrastinators.

But the Knicks weren’t procrastinating. They just couldn’t find a compromise. And now, Quickley’s future is murky.

(Photo of Immanuel Quickley: Sarah Stier / Getty Images)

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