NBA players employ agents whose jobs are, basically, to make contract negotiations difficult for the teams on the other side of the table. Their aim is to get their client the most favorable deal possible, which almost always means something different than what's best for the team.

That framing means every contract decision is adversarial and contentious by design. The whole process is destined to be difficult.

The contract decisions we'll cover here start with those competing interests and inherent conflicts and then layer more complicating factors on top. Sentiment, emotion, preexisting relationships and the powerful leverage of a player knowing his team's management will be screwed/reviled by fans/possibly fired if he leaves make the following contract situations the trickiest of all.

Maybe these offseason negotiations won't all be knock-down, drag-out all-nighters that go down to the last pre-deadline second. But none of them figure to be easy.


Kyrie Irving, Dallas Mavericks

Talent is paramount in the NBA, and Kyrie Irving has loads of it. But as the Dallas Mavericks navigate a thorny roster-building bramble this offseason that includes Irving's free agency, they'll have to wonder whether Irving is the right kind of talent to put alongside Luka Doncic. That evaluation will require acknowledging the team's 5-11 record in games the two played together and the related slide from fourth to 11th in the West.

Dallas has few routes to improve its roster outside of retaining Irving. It could renounce its rights to several free agents (including Irving) to clear $20-30 million in cap space. From there, the Mavs would have to hope Khris Middleton (player option), Draymond Green (player option) or some other veteran worthy of a pricey deal becomes available.

They could also sign-and-trade Irving elsewhere, but that would require cooperation from him and another team. That's a tricky two-step considering how few organizations would want to give up significant assets for the mercurial point guard. The only teams that seem like semi-realistic options for this route are the Los Angeles Lakers and Phoenix Suns. They were linked to Irving when he initially made his trade request, but both of them made other acquisitions at this year's deadline that they should probably prefer over Irving.

Ultimately, Dallas seems stuck. It gave up Dorian Finney-Smith, Spencer Dinwiddie and a future first-rounder for Irving and may have no choice but to meet his contract demands. Letting him walk for nothing a year after Jalen Brunson did the same would be too much to handle.

With a potential new deal topping out at five years and $272 million, a win for the Mavericks might be shaving off a few years or dollars from that contract. Irving has averaged 56 games per season for his career and has topped that number only once since 2018-19.

Add to that a track record of unreliability and controversy so long there'll be books written about it one day, including his refusal to get the COVID-19 vaccine and his initial failure to apologize and denounce antisemitism after promoting an antisemitic film on social media last fall, and the "safe" play of simply re-signing Irving feels remarkably dangerous.


James Harden, Philadelphia 76ers

It feels like we were just here with James Harden, but the Philadelphia 76ers guard and league leader in assists can get right back on the free-agent market this summer by declining his $35.6 million player option in the contract he signed last offseason.

That contract, which required Harden to decline a whopping $47.4 million player option, triggered a tampering investigation by the NBA. Somehow, what happens with Harden this time around might be even more intriguing.

According to ESPN's Adrian Wojnarowski, Harden is considering a return to the Houston Rockets. The Athletic's Sam Amick and Kelly Iko confirmed that not only is Harden open to a second go-round with Houston, but that the team is also expected to pursue him.

Even if he's more of a facilitator now, and even if his defensive shortcomings and mileage (2023-24 will be his age-34 season) suggest the downside risk is substantial, Harden is going to command a sizable free-agent contract. He just turned in his third career season with averages of at least 21 points and 10 assists while posting a true shooting percentage north of 60. Only two others in NBA history have even one such campaign on their resumes: Magic Johnson and Kevin Johnson.

Production like that is worth paying for.

Much will depend on the length of the Sixers' 2023 playoff run and how much Harden has to do with whatever success they enjoy. Another playoff flameout in a career full of them could lead to a chillier market than expected. Still, assuming Harden opts out, the Sixers will have to weigh many factors when deciding what to do about his free agency.

If Joel Embiid vouches for Harden, Philadelphia may have no choice but to pay whatever it costs to keep him. If the Rockets drive up the price, the Sixers may be similarly stuck spending more or offering a deal that spans longer than they'd prefer. And that's to say nothing of the possibility that Harden simply wants to go back to Houston, regardless of what other offers are available.