The $108 million Dan Gilbert spent on payroll had just paid off in the biggest way, and nearly everyone associated with the Cleveland Cavaliers, from LeBron James on down, wanted to celebrate.
So in the immediate hours after the Cavs’ stunning Game 7 win over Golden State in the 2016 NBA Finals, Gilbert flew the team’s traveling party from Oakland, Calif., to Las Vegas. The Cavs were posted up at the Wynn, and more specifically, the XS Nightclub, where J.R. Smith sprayed bottle after bottle of champagne into the air.
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Two members of the Cavs’ traveling party really wanted into that club — Gilbert’s sons, Grant and Nicholas. But neither was 21, so up to the hotel room they went.
Winning that title for Cleveland was Gilbert’s sports dream and his mission since 2005 when he bought the team. By the time luxury taxes were counted for the 2016 season, Gilbert paid $161 million to build a championship roster. He’d earned the right to pop some champagne in the desert.
While the Cavs partied until it was time to board the plane to come home, however, Dan instead spent those hours with his boys, picking over room service pizza and watching replays and interviews from Game 7 on the flat-screen TV hanging on the wall.
“That moment is a great sort of spotlight of who my dad is just as a father and a person,” Grant said in an interview. “Nick was a little upset that we couldn’t get in and party, but just seeing my dad, if he’s not there (in the club), then what do we have to complain about? It was a surreal moment, and I think we were going deep into talking about lottery moments and looking back at some things we have experienced together. Not just us three, but our whole family and how it led to this point.”
Grant was a child when his father purchased controlling interest of the franchise and was a floppy-haired teenager when he posed for pictures with Kyrie Irving in New Jersey the night the Cavs won the lottery in 2011 to earn the No. 1 overall pick. That photo with his father, Nick and Irving remains the background image on Grant’s computer. The night the Gilberts spent in that Vegas hotel, while the Cavs partied downstairs and Clevelanders danced in the streets, remains one of his fondest memories.
Grant, now 23, is on the fast track as his father’s heir apparent. Dan remains in a wheelchair from his May 26, 2019, stroke, convalescing over the winter in Florida, and has not been to a game since the stroke. The 59-year-old billionaire, mortgage and real-estate mogul and family patriarch has not been able to use the left side of his body during his few public appearances. Cavs officials insist Dan remains in communication with his chief lieutenants, but how he does that has changed, and his absence, compared to how much he used to be involved with the Cavs, is a constant piece of chatter in NBA circles.
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Enter Grant, who already has a job with the Cavs, and it’s no entry-level position. He is the team’s director of content and brand strategy, which is on the business side of the organization but consults enough with the basketball operations side to be “in the know” on what general manager Koby Altman and staff are up to.
When it comes to the question of his future inside his father’s organization, and whether he’ll one day take over, Grant insists he is not “on a linear path” to assuming his father’s seat. He humbly points to his age, his inexperience and a full life he has yet to lead. In other words, he doesn’t know if this is even a job he wants.
“That’s not my everyday focus,” Grant said. “I’m not making decisions and planning my life based on that. There are a lot of things I want to do. I’m sure there are a lot of things I don’t know that I want to do that, hopefully, I’ll end up doing. But in terms of staying engaged and helping impact and being involved (with the Cavs), that’s something I want to do for the rest of my life.”
Had nothing ever happened to Dan Gilbert, Grant said he would still be in this job working for his father’s basketball team. He still would have moved into a downtown Cleveland apartment and would have rolled up his sleeves to meet as many people as he could in the organization and learn the business.
There is an entire story to tell about what Grant does for the Cavs now, the passion he has for his specific line of work and his insistence that he does not act like the boss’ son. How he has managed a new job in the COVID-19 era, how he hasn’t even gotten to have a drink with colleagues he works with every day because he sees them only on Zoom calls.
But Dan did suffer a stroke, and it totally changed how he wields his enormous influence inside the Cavs’ business and basketball offices — all while Grant is not only working in Cleveland, but also texting players and laughing with them at practice, and chatting with basketball decision-makers and joking with agents. The vacuum created by Dan’s departure from his past routines, while Grant has been so visible around the team this season, is part of the reason for the widespread speculation about Grant’s future.
Cavaliers owner Dan Gilbert and his two sons, Grant (far left) and Nick at the 2011 NBA Draft lottery. (Photo by Jesse D. Garrabrant / Getty Images)“He’s definitely gonna take over,” said one source, who does business constantly with Cavs’ basketball operations. “His dad’s not able, and he’s the next in line.”
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“Gilbert’s son is running the show behind the scenes,” said a second league source.
“Grant’s trying to take a bigger role,” said a third source with knowledge of the Cavs’ operations. “But (he has) zero experience.”
The Cavs vigorously refute this, but even their pushback against it is nuanced. They say the “culture” Dan Gilbert created is still very much in place, and he remains at the center of it. They say he has “great ideas,” and they insist Dan, not Grant, is the boss.
“His presence may not physically be in Cleveland like it was prior to (the stroke), coming into 30-plus games a year or whatever it was, but his presence in the business, in the culture, and kind of how we’re operating, he’s absolutely still the author of all those things,” said Nick Barlage, who serves as president of Cavs’ business operations.
Since the stroke, Dan has divested some of his business interests, including his stake in the JACK Entertainment casinos, which he launched in Cleveland in 2012. Last summer, after 35 years as a privately held company, Quicken Loans went public — something Dan swore for years he’d never do.
Cavs chief executive officer Len Komoroski and Jason Hillman, the Cavs’ chief of staff and general counsel, have sat on some of the NBA’s Board of Governors calls in Gilbert’s place. Hillman has been with the Cavs since 2005, essentially serving as the organization’s lawyer on the business side. He became chief of staff to Altman in 2017.
Jay Farner and Matt Rizik, two of Gilbert’s closest business associates, handle many ownership duties, according to multiple sources with knowledge of the Cavs. Farner has been with Quicken Loans and now Rocket Mortgage for more than 20 years, while Rizik is the company’s chief tax officer and manager of Gilbert’s family office. They are handling the financials and serving as the conduit between the front office and ownership, multiple sources said.
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How is all of this different from the way things used to run under Dan Gilbert? For better or worse, he has been the driving force fueling the Cavaliers for the last 15 years. His numerous and lengthy emails and text messages to team employees at all hours of the day and night remain legendary. He published The Letter the night LeBron left in 2010. For years he diminished the role of his top executives and stripped the power from his GMs. Even Tyronn Lue and David Griffin, the head coach and GM, respectively, who helped deliver Cleveland a title, couldn’t survive under Gilbert.
This is still Dan Gilbert’s empire. It’s his money and his team. His monetary investments in his mortgage and real estate businesses in Cleveland, as well as in the basketball arena — Rocket Mortgage FieldHouse — have grown over the last two years. And there is no plan to sell, says not only Grant but also a longtime spokesman for Dan. While team officials say Dan Gilbert is still consulted on things like trades for players, he spent every moment as chairman up until his stroke as the fuel that propelled the organization. While Dan is not nearly as active, Grant’s contact with those same front-office members has increased.
“I’m involved to the extent that I’m in the know,” Grant said. “I don’t try to help make decisions. I don’t even pretend to try to make decisions when I know I don’t have the credibility or experience to do so.”
The Cavs grudgingly made Grant available for an interview only after learning The Athletic was pursuing a story on his rise within the organization.
Neither Grant nor the Cavs deny an eventual ascension to chairman of the team is something that could happen for the second-oldest Gilbert child, but if it does, it would be something that occurred potentially down the road.
“For me to try to make an impact and for me to feel like I have a voice and credibility and to help make decisions, I have to know people,” Grant said. “I have to have conversations, I have to have personal relationships. If … I’m just coming in as Dan’s son, it can be interpreted in a different way. Whereas now I’m in Cleveland and I’ve been working full time for nine, 10 months. I have personal relationships with everyone. We’re co-workers, we’re friends, we’re understanding, and I just think it’s a really good dynamic. I’m very happy that I ended up moving down here.”
(Photo courtesy the Cleveland Cavaliers)Gilbert isn’t the stereotypical entitled, bratty rich kid. Those who know him gush about his manners and how eager he is to learn.
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“Just a good dude,” said one Cavs player.
“He’s not what you’d expect,” said another source who has known Grant for years. “I’ve always found him to be extremely polite, very intelligent and very respectful. He was always a good kid.”
“He’s a quick learner and pursues what he doesn’t know,” said Barlage, who oversees the Cavs’ business operations. “He has a natural curiosity that takes flight from a foundation of a very humanistic and normal approach. That’s a tribute to how he has been raised and who he is as a person.”
For now, Grant insists, his passion remains blending sports with culture and art. He played a key role in the team hiring renowned artist Daniel Arsham as creative director, and then connecting Arsham to numerous projects across several departments (court design, retail, art inside the arena). Grant also had a voice in designing the “City Team” jerseys, he negotiated the deal to bring a Cavs-centric podcast under team control and worked on branding projects for the city and the team hosting the 2022 NBA All-Star Game.
Grant does not have any employees under him in the Cavs’ organization, and he reports to at least two upper-level managers. To hear him describe his own role, it sounds like he is a roving consultant, working with in-house marketers, designers and promoters. He points out that any new team jersey is a collaborative project with not only the NBA, but also Nike, and the approval process can take months, if not years — which meant the work on the “City Team” jersey began while he was still in college.
“I’m not the sole voice in making decisions, where it’s my way or the highway, but I provide a unique perspective and opinions that can obviously be disputed,” he said. “I think everyone’s under the impression that that’s a thing, but I’m going to try to express myself and provide new things and try to do things that are more innovative and creative.
“I’ve never once made a decision since I started where it was like, ‘OK, we’re going to do this.’ I say, ‘I think we should do this, I think this would be the right move, but it’s up to you guys.”
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Grant graduated from Michigan in May, a surprising feat in and of itself. His father is a Michigan State alum and major donor, as is his mother, Jennifer. Nick is also a Michigan State alum.
Grant says his father gave no pushback about him choosing the Wolverines over the Spartans but did try to persuade his son to try pursuing a college basketball experience at a Division III school (Grant was a 5-foot-11 point guard in high school, a three-year varsity player and two-year captain). He enrolled at Michigan and was a general studies major, he said, with a focus on accounting, entrepreneurship and psychology. He said he enjoyed college, especially socially, but as time wore on was drawn to his parents’ vast philanthropic efforts as well as the business of working in basketball. And he wanted to get started right away.
“I’ve always been obsessed with basketball,” Grant said.
Grant has an idealistic streak. He is drawn not only to Cleveland, his current home, but also to Detroit, another Rust Belt capital known to the outside world as aging, barren former metropolises that have battled blight, bankruptcies, and in Cleveland’s case, a river that caught on fire. He said he thinks he can change the perception of Cleveland by working on the Cavs’ brand, strengthening it to the point where it stands and connects with people outside of basketball.
The NBA has plenty of examples of legacy ownership situations. The Buss family with the Lakers. The Arisons in Miami. The Kroenkes in Denver, just to name a few. There is a reason “family business” is a cliche — it is part of why there is such a wide assumption that Grant is being groomed to take over for his dad.
In the interview, Grant just asked that his life not be pre-determined for him. But if he were to one day ascend to chairman of the Cavaliers, it’s fair to wonder if he will follow Dan’s example as a hands-on owner.
Altman, the Cavs’ current GM, is the first under Gilbert’s ownership to receive a contract extension. He also has been in the organization since 2012 and has known Grant for that long. That’s why Grant feels as comfortable as he does interacting with Altman and the front office.
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“He and I have always had a good relationship,” Grant said. “We text every day about stuff that has nothing to do with Cavs basketball.”
One day, the subject matter of those texts might change.
(Top photo courtesy Cleveland Cavaliers)
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