What happens when LeBron James decides one more championship is worth more than money? History suggests that his free-agency decision rarely affects just one franchise. It happened in Miami, where Mike Miller and Shane Battier became key pieces around the newly formed Big Three. Cleveland saw Richard Jefferson and Channing Frye arrive as the Cavaliers built a championship roster around James’ return. Even in Los Angeles, Dwight Howard’s comeback and Markieff Morris’ midseason addition became part of a veteran group that helped deliver the Lakers’ 2020 title.

Philadelphia appears to be following that familiar script already. James’ move to the City of Brotherly Love was never about one final blockbuster payday. A two-year, $8 million contract made that much clear. It was about giving himself one more legitimate shot at a championship, even if that meant joining a franchise still trying to end a title drought dating back to 1983. And history has often shown that once James commits to a contender, he rarely remains the only championship-tested veteran looking in that direction.

According to senior NBA insider Chris Haynes, Kentavious Caldwell-Pope and the Memphis Grizzlies are currently negotiating a buyout. If that’s cleared, the 2x NBA champion intends to sign with Philadelphia.

“Kentavious Caldwell-Pope and Memphis Grizzlies are negotiating a buyout, and the veteran 3-&-D specialist intends to team back up with LeBron James and sign with the Philadelphia 76ers, league sources tell me,” Haynes directly reported.

Caldwell-Pope previously won an NBA championship alongside James with the Los Angeles Lakers in 2020 before capturing a second ring as Denver’s starting shooting guard in 2023. But the reunion goes beyond familiarity.

The reunion is about more than familiarity. Throughout his career, Caldwell-Pope has consistently thrived alongside ball-dominant superstars without needing touches of his own. Whether next to James in Los Angeles or Nikola Jokić in Denver, his value came from defending elite perimeter scorers, spacing the floor and embracing one of basketball’s least glamorous roles. For a Philadelphia team already built around high-usage stars such as James, Joel Embiid, Tyrese Maxey and Jaylen Brown, that archetype arguably fills a bigger need than adding another offensive creator.

His numbers from last season don’t immediately jump off the page. Caldwell-Pope averaged 8.4 points while shooting a career-low 31.6% from three before his campaign ended following surgery on his right pinkie. But Philadelphia would be betting on a much larger body of work. Prior to last season, he had shot better than 40% from deep across a five-year stretch while building a reputation as one of the league’s more dependable two-way role players and a full-time starter on two championship teams.

While Caldwell-Pope’s interest in joining Philadelphia appears straightforward, actually completing the move is considerably more complicated. The first hurdle isn’t Philadelphia at all.

Caldwell-Pope remains under contract with Memphis, meaning the Grizzlies and the veteran guard must first complete a buyout. Until that happens, the Sixers cannot officially sign him despite his reported intention to reunite with James. And even if the buyout is finalized, Philadelphia still faces a second, and perhaps bigger, challenge.

The obstacle isn’t convincing Caldwell-Pope to join; it’s creating enough room to sign him. Because the Sixers are hard-capped at the NBA’s first apron, they cannot temporarily exceed that spending limit to complete the move. Every dollar, and every roster spot, must already fit within the league’s restrictions before Caldwell-Pope can officially be added, even if he’s ultimately expected to sign for a veteran-minimum contract.

Brian Windhorst immediately assembled a panel featuring Tim MacMahon and Bobby Marks on ESPN’s The Hoop Collective after James agreed to his two-year, $8 million deal, with the discussion quickly shifting to what Philadelphia would have to do next.

Windhorst pointed out the financial reality: “So, right now they have 14 players under contract and they only have $3.3 million under their hard cap. So, they are going to have to waive a couple of players.”

Windhorst’s point wasn’t simply that Philadelphia needs to trim salary. The Sixers currently have 14 standard contracts on the books, meaning they must also free a roster spot before adding Caldwell-Pope. Put differently, Philadelphia’s biggest obstacle isn’t recruiting the veteran guard; it’s navigating the NBA’s roster and salary-cap rules in the correct order so the signing becomes legally possible. Bobby Marks then identified the contracts most likely to become casualties.

“Yeah, they’ll have to waive. They’ve got two guys. Dalen Terry’s on a non-guarantee. Jabari Walker’s on a partial $250 grand. They could try to maybe move off of Johni Broome they picked in the second round a year ago. They could do something there. They’ll figure it out.”

Those names weren’t mentioned because they’re central to Philadelphia’s long-term plans. They surfaced because their contracts are among the easiest to move. Terry’s salary is fully non-guaranteed, while only a small portion of Walker’s deal is guaranteed. Waiving one, or, if necessary, more than one, would free both cap space and roster flexibility, allowing Philadelphia to fit Caldwell-Pope beneath the first apron without dismantling its core rotation.

Windhorst then connected the cap mechanics directly to James’ contract, explaining how adding Caldwell-Pope, who is also represented by Klutch Sports, could affect the team’s flexibility.

“They may come to LeBron and say, ‘LeBron, if you want us to sign another player, Kentavious Caldwell-Pope, for example… If you want us to sign another player, you need to sign a one-year deal.’ Is that correct?”

Marks replied: “Correct.”

Despite those hurdles, Windhorst believes Philadelphia’s healthy lineup would immediately rank among the NBA’s most formidable.

“As far as the Sixers go, you would think that their starting lineup when they’re fully healthy… is Edgecombe and Maxey at the guards, Brown and LeBron at the forwards, and Embiid at center. That’s loaded… the most athletic backcourt in the NBA.”

The question is no longer whether Caldwell-Pope wants to reunite with James; Haynes’ reporting has already answered that. The real intrigue now lies with Philadelphia’s front office.