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A Brief History of the Complicated Relationship Between LeBron James and Dan Gilbert

LeBron’s history with the Cavs owner is long and messy. How did they get here? And where do they stand now, about a month from another big decision? We break it down, FAQ-style.

LeBron James and Dan Gilbert AP Images/Ringer illustration

Cleveland’s roster is a daily, unavoidable reminder that someone messed up, in the same way that a carpet stain by the front door is. No one feels that more intimately than LeBron James. He was 2 feet away from J.R. Smith in Game 1 when Smith forgot that the score was tied on the last possession, sending the game to overtime. In Game 2, James was forced to endure eight more minutes of Jordan Clarkson scraping the bottom of NBA Finals history.

You could make the argument that LBJ is at least partly responsible for the personnel flaws. The Cavs paid the price to acquire or retain players to help James win titles, including handing out hefty contracts for Smith and Tristan Thompson (who are represented by Klutch Sports, the agency run by LeBron’s close friend Rich Paul). But the landslide of blame for this edition of the Cavs falls on their owner, Dan Gilbert, who let his general manager walk days before the draft and oversaw the trade of his second-best player, all in the same summer.

The complicated history between LeBron and Gilbert goes way back; their past isn’t storied, it’s nightmarish. And with the Cavs now down 2-0 to Golden State and LeBron able to hit free agency this summer, their relationship could soon be over. Again. With another pivotal offseason in Cleveland drawing closer with each loss to the Warriors, here’s an FAQ on the long and messy saga that is LeDan (DanBron?):

Where Do LeBron James and Dan Gilbert Stand?

Well, there’s this:

In an interview with Rachel Nichols before Game 1 of the Finals, LeBron said he wouldn’t make any free-agency decisions until the playoffs end. (Before the season began, Gilbert reportedly asked LeBron to pledge loyalty past 2017-18. He didn’t.) “It’s not about me and Dan,” LeBron said. But later in the interview, when Nichols asked whether their relationship would affect his decision to stay or leave, James said, “We’re going to see.”

Gilbert made comments earlier that week that felt like an attempt to change the subject. “Like him, I think he’s said this, we’re just focused,” he told ESPN, “and it’s the truth, it’s not avoiding the question—we’re literally focused on [the now].” We’re. Focusing on the championship is very much LeBron’s responsibility; focusing on the franchise’s future is the front office’s—one that Gilbert plays a heavy role in.

Is Gilbert to Blame for the Roster Around LeBron?

The summer after Cleveland’s third straight trip to the Finals, and just 13 days before free agency commenced, Gilbert allowed general manager David Griffin’s contract to expire. An executive told The Ringer’s Kevin O’Connor later in the summer of 2017 that Gilbert’s M.O. was “a state of organizational chaos.”

Cleveland would lose another major piece of its 2015-16 championship team two months later. Kyrie Irving, after asking for a trade in July, was dealt to the Boston Celtics for Brooklyn’s 2018 first-round pick, Isaiah Thomas, Jae Crowder, Ante Zizic, and a 2020 second-round pick. Before Griffin was let go, he was reportedly working on deals that would have shipped out Kevin Love for Jimmy Butler, or Kyrie for Paul George. The proposals could’ve been executed after Griffin left, according to Cleveland.com. But the Cavs didn’t appoint a new GM until a month after Griffin left.

In the meantime, Gilbert was the driving force behind the trade with the Celtics, O’Connor reported last August. The owner jonesed for the Brooklyn pick above all else as a way to walk the line between a future with and without LeBron, even after the severity of Thomas’s hip injury was revealed. By the end of the season, the Cavs ended up with the eighth overall pick in the 2018 NBA draft, a month of Thomas being grumpy in the locker room, George Hill, Larry Nance Jr., Clarkson, the loss of their own 2018 draft pick, and Rodney Hood, who is averaging 2.1 minutes in the Finals.

How Did LeBron Feel About the Transactions?

James advocated for Griffin last April: “It makes no sense why he shouldn’t get an extension,” he told ESPN. “We wouldn’t be in this position, obviously, without him.” For someone who can get pretty cryptic, James laid out, point-blank, what would make him happy. Three months later, on the day Gilbert and Griffin parted ways, LeBron took to Twitter. “If no one appreciated you Griff,” he wrote, “I did.”

LeBron also addressed the Kyrie trade in his recent interview with Nichols. At the time, it seemed like James abstained from getting involved as Irving expressed unwillingness to play in LeBron’s shadow. But after a Cavs season in which Jose Calderon started the most games at point guard, James confirmed that he asked management over the summer not to trade Irving.

“I felt like it was just bad for our franchise just to be able to trade away our superstar point guard,” James said. “A guy that I had been in so many battles with over the last three years, and obviously I wasn’t a part of the communications and know exactly what went on between the two sides, but I just felt like it was bad timing for our team to just get rid of our point guard in Kyrie Irving.”

Where Did the Beef Originate?

It traces back to the last time LeBron was a free agent, in 2010. I’ll keep this brief, because of all the decisions ever made in history, like putting a man in space and Supreme Court rulings and Rihanna’s CFDA dress, The Decision can refer to only one thing.

James took his talents to South Beach. He’s since expressed regret at the flashy nature of his announcement, a live televised special that led to heaps of polyester going up in flames and 427 very distasteful words from the owner.

“Some people think they should go to heaven,” Gilbert wrote in a letter posted on the team’s website that night, “but NOT have to die to get there.” The entire letter was bizarre, from the font (an iconic choice: Comic Sans) to the personal guarantee that Cleveland would win a title before LeBron would (didn’t he just spend five years watching LeBron?) to the misuse of quotation marks (“The self-declared former ‘King’ will be taking the ‘curse’ with him down south. And until he does ‘right’ by Cleveland …”). But more so, it was offensive. Gilbert called James’s departure a “cowardly betrayal,” a “shameful display of selfishness,” and the “exact opposite lesson of what we would want our children to learn.” The league fined Gilbert $100,000, but it didn’t deter him from continuing to speak on the matter. In 2011, after LeBron’s Miami team lost to Dallas in the Finals, Gilbert tweeted, “Congrats to Mark C. & entire Mavs org. Mavs NEVER stopped & now entire franchise gets rings. Old Lesson for all: There are NO SHORTCUTS. NONE.”

Gilbert’s reaction crossed many lines, including some that James will never forget. Last October, James, then three seasons into his second tenure in Cleveland, told GQ that he felt the letter was related to his blackness.

“It was another conversation I had to have with my kids [...],” James said. “It pops in my head a few times here, a few times there. I mean, it’s just human nature. I think that had a lot to do with race at that time.”

So It Wasn’t Water Under the Bridge When LeBron Returned in 2014?

There was some speculation that Gilbert’s presence was going to botch the deal altogether. “If it wasn’t for that letter, this would’ve been done awhile ago,” one source told ESPN in early July 2014. Even after being fined, Gilbert’s letter remained on the Cavs’ website for four years, and was removed only days before 2014’s free agency began. Years later, Dan Patrick said a source told him that LeBron even tried to get the Pistons and Cavs to switch ownership before signing. (Gilbert was born and raised in Michigan, and Quicken Loans, his mortgage lending company, is headquartered there.)

“LeBron did not want to play for Dan Gilbert the second time around,” Patrick said in 2017. “He wanted to go back to Cleveland. He didn’t want to play for Dan Gilbert.” In the wake of The Decision, Gilbert was also one of the most vocal owners in opposition to bending to the players in CBA negotiations during the 2011 lockout. In the end, the new punitive luxury tax installed by the CBA made it tough for superteams—like, say, LeBron’s Heat—to stay together.

Once James signaled that he was considering going home, Gilbert flew to Florida in the summer of 2014 to reconcile. “We had five great years together and one terrible night,” Gilbert said. “I told him I wish I had never done it, that I wish I could take it back.” (Gilbert also said, “I told LeBron, ‘That letter didn’t hurt anybody more than it hurt me.’” Which, OK; it was left on the website until the week before the meeting, but sure.)

LeBron echoed the sentiment nearly verbatim: “We had one bad moment and it just overshadowed all the great times we had together. Now we’re back together. We both have something in common, and that’s to bring a championship to this city.”

Is Anything Else From Their Past Relevant to LeBron’s Possible Free Agency?

“It’s our job as owners and management to build a team around [LeBron] that can win championships, and hopefully multiple ones.” That was one of the first things Gilbert said after buying the Cavs in 2005. Failing to do so is why LeBron left eight years ago. “We could not bring in enough talent to help us get to what my vision was,” James told GQ last October.

It’s hard to watch the Cavs this postseason and not feel like history is repeating itself. In 2012, after James won his first ring with the Heat, Gilbert even said that he wouldn’t cater to a star the way he did in James’s first tenure.

”The key thing, whoever you are and wherever you are, you can not wait,” Gilbert said. “The big lesson was if a player is not willing to extend, no matter who they are, no matter where they are playing, no matter what kind of season you had, you can not risk going into a summer and having them leave in unrestricted free agency and get nothing back for it.”

Gilbert has made some efforts to this end, most notably by pearl-clutching the Brooklyn pick as a way to get a head start on a possible post-LeBron era. But James can still walk away this summer as an unrestricted free agent and leave the Cavs with nothing in return.