After a long, contentious negotiation, Jalen Duren finally landed a $200 million deal, but the Detroit Pistons were hesitant to max out their All-NBA/All-Star.

Long-term contract negotiations are a complex dance: Teams worry about luxury taxes and aprons, but also fear losing talent if they don't offer enough.

Many deals become significant miscalculations that teams wish they could remove from their salary-cap books through an amnesty provision, as the 2011 collective bargaining agreement allowed for eligible contracts. The longer and uglier the deal, the harder it is to move.

Those contracts can limit flexibility and shorten the championship window for former MVPs. Recently, teams have offered shorter contracts with less guaranteed money. Still, the damage is done in the following cases.

Gary Trent Jr., Milwaukee Bucks

Didn't the Milwaukee Bucks re-sign Gary Trent Jr. to a four-year, $64 million contract?

Fresh off a season averaging 8.1 points per game, the 27-year-old wing got a deal that confused most competing executives.

With the Bucks retooling after trading Giannis Antetokounmpo to the Miami Heat, that heavy an investment in Trent is difficult to justify based on his projected contributions over the next four seasons.

Trent can shoot. He can play 20 minutes a game, but he's been a near-minimum player the last few years. The size of the raise is difficult to justify, and his contract could age poorly.

Immanuel Quickley and Jakob Poeltl, Toronto Raptors

The Toronto Raptors brought Kawhi Leonard back in a trade from the LA Clippers, costing several first-round picks. The Raptors have struggled recently to build a contender while working around the tax and first apron. The team returned to the playoffs after a three-year absence, and Leonard will make Toronto better when he's healthy.

The challenge is the $97.5 million owed to Immanuel Quickley over three years at a flat rate of $32.5 million. He's productive when he plays, but he's struggled with durability.

Similarly, Jakob Poeltl is due up to $104 million over four years, depending on incentives. His final season is partially guaranteed, but there has been little trade interest in the Raptors' oft-injured center.

Jamal Shead and Collin Murray-Boyles provided steady production. With Scottie Barnes and Leonard earning almost $92 million next season, Toronto has way too much invested in Quickley and Poeltl.

PJ Washington, Dallas Mavericks

The Dallas Mavericks have too many forwards. From Rookie of the Year Cooper Flagg to recent trade acquisitions Santi Aldama and Zaccharie Risacher, the Mavs don't have the budget for PJ Washington, the second-highest-paid player on the team behind Kyrie Irving.

Washington is in the first year of a four-year, $88.8 million extension. The Mavericks also drafted Morez Johnson Jr., re-signed Moussa Cisse, and re-signed Dwight Powell. Washington is better suited elsewhere on a contender, where he'd fit in as a complementary role player.

While his $19.8 million salary isn't outrageous this season, the length and total value of his contract could make him difficult to trade.

Christian Braun, Denver Nuggets

Since their 2022-23 championship, the Denver Nuggets have struggled to keep their roster together around MVP Nikola Jokić.

Following the departures of players such as Michael Porter Jr., Kentavious Caldwell-Pope and Peyton Watson, even a core featuring Jokić, Jamal Murray and Aaron Gordon has been unable to take Denver back to the NBA Finals.

The Nuggets hoped Christian Braun, their No. 21 pick in 2022, would take on a larger role. His five-year, $125 million rookie-scale extension begins this season with a $21.6 million salary.

Unfortunately for Denver, Braun played just 44 games last season, and his three-point shooting dropped from 39.7 percent in 2024-25 to 30.1 percent.

Given the open looks Jokić creates, the Nuggets need Braun to space the floor reliably. Their financial commitment to him could become a major obstacle if he doesn't improve this season.

De'Aaron Fox, San Antonio Spurs

Should De'Aaron Fox be on the list, as the starting point guard of the San Antonio Spurs squad that advanced to the NBA Finals?

But then, the Spurs may not have known how quickly Dylan Harper would emerge as a powerful rookie contributor.

Fox is the team's highest-paid player this season, earning $49.5 million and with almost $222 million due over four years. All-Star Victor Wembanyama jumps from $16.8 million to about $43 million in 2027-28, and standout guard Stephon Castle will be right behind him with an extension due before the 2028-29 campaign.

Fox, who turns 29 in December, is signed into his early thirties. He shot just 31 percent from three-point range in 2025-26 and made several costly decisions in the NBA Finals against the New York Knicks.

While Fox shouldn't be the scapegoat for the Spurs' loss, he was brought in from the Sacramento Kings to provide veteran leadership as San Antonio's young guys developed. Still, they've eclipsed him in importance, which is problematic given his long, massive contract.

The Spurs likely won't resolve this for some time, as there will be few or no trade suitors.