In private, Mark Cuban has started discussing his role in national politics with his family.
He told Business Insider, for instance, that he spoke with loved ones about his decision to campaign on the trail for Democratic presidential candidate Hillary Clinton.
"We discussed how much of a threat I believe Trump to be," Cuban said in an email. "We discussed why it was important to me to get involved — that if I could have an impact and didn't try, it would have left me guessing forever."
And, as Cuban said, his family feels "like we started on the right path" to "have a platform and voice for the future."
Cuban, 58, is a self-made billionaire businessman and the owner of the Dallas Mavericks. And he seems more serious than ever about running for president.
Cuban refrained from engaging much in politics before the 2016 campaign cycle. But in the past two years he has openly flirted with a White House bid, teasing journalists with tantalizing words about his aspirations.
It wasn't long ago that Cuban was shutting down questions about whether he'd seek the presidency one day, flatly rejecting the notion, as he did at the September presidential debate.
But something changed. It was, as Cuban put it, "obvious": the election — unpredictability — of Trump.
"What I do depends on how things play out for the country," Cuban said referring to a 2020 attempt at unseating Trump.
Like Trump, Cuban introduced himself to American households first as a prominent businessman and later through a reality-TV show. He had no formal history in politics, only suddenly emerging on the national political stage last year. His strategy for gaining political prominence was oddly similar to Trump's — deliver hot, unadulterated takes on cable TV, outlets like CNBC, Fox News, and CNN, and on Twitter.
Yet Cuban does not embrace the comparison.
"He talked about running for office for 30 years," Cuban said. "I started talking about politics this year, after avoiding them the last almost 20 years, because I thought it was important to do so."
In conversations with Business Insider, Cuban's longtime friends said they were initially surprised to see Cuban get involved politically, but they added that they could certainly now envision him entering the fray in 2020. And while it would be a climb to the White House for the tech titan, campaign experts have laid out a path Cuban could take to find himself in the Oval Office.
Rising profile
With Trump's improbable rise to the presidency, there's been no shortage of ultrawealthy, prominent business people rumored to be considering a run of their own in 2020.
There's Oprah Winfrey, Mark Zuckerberg, Starbucks CEO Howard Schultz, and Disney CEO Bob Iger, all of whom have fed the idea that Trump could face a fellow executive in his prospective 2020 reelection bid. But no nonpolitician has put him or herself out there quite like Cuban.
Cuban, who grew up in the suburbs of Pittsburgh, moved to Dallas in the early 1980s, finding work as a bartender. He caught his first big break after he started a software company, MicroSolutions, which he sold in 1990 for $6 million. But his biggest break came after he founded AudioNet, which became Broadcast.com, the streaming site he sold to Yahoo at the peak of the dot-com boom in 1999 for more than $5 billion in stock. A year later, he'd buy the Dallas Mavericks and become one of the NBA's most recognizable, and outspoken, owners.
He showed minimal interest in politics in his years since striking it rich — until 2016, when his political presence grew exponentially after he started roiling Trump along the campaign trail.
Initially, Cuban was warm to Trump, speaking about him in positive terms. But that eventually changed, and Cuban found himself delivering blistering stump speeches for Clinton and ripping Trump on a number of issues, including his wealth.
When Trump won the presidency, Cuban went quiet again, ceasing his attacks on the country's newly elected leader.
That lasted only so long, though. When Trump ignited chaos after signing his executive order on travel from certain majority-Muslim countries, Cuban appeared on several networks to voice his displeasure with both the decision and the president. He unleashed a bevy of tweets at the commander-in-chief, staking out a place as the de-facto leader of opposition among the small community of ultrawealthy business people.
And Cuban has been merciless since. He has called Trump "the Zoolander president." He has suggested Trump wouldn't be able to find the "C" if he was spotted the "A" and "B."
Cuban, in a now deleted tweet, said he was "crushing" Trump because the president "earned it."
That appeared to get under Trump's skin.
Last month, Trump fired a shot at Cuban on Twitter, suggesting he was not "smart enough" to win the presidency — a claim Chris Sacca, the billionaire venture capitalist and "Shark Tank" costar, seemed to disagree with in an email to Business Insider.
"Only Mark can speak to his long-term ambitions in politics," Sacca said. "But unlike Donald, Mark is smart, reads extensively, and is willing to ask others for help and listen to their advice on issues that matter."
But Trump isn't alone in his criticism. Cuban's newfound political platform has left him with a growing set of critics. One of them is Frank Zaccanelli, a Dallas real-estate mogul who was a part of the Mavericks ownership group headed by Texas billionaire Ross Perot Jr., who sold the team to Cuban in 2000.
Zaccanelli, who calls himself a "pretty good student of Mark Cuban" although he "wouldn't say we're best friends or get along great," blasted Cuban for some of his statements and decisions during his de-facto tenure as Trump's foil in the business world.
"What he's doing now has put himself out there for a lot of criticism," Zaccanelli said.
The former Mavericks executive was particularly dismayed by Cuban's February tweet to a season ticket holder who was upset by the owner's comments about Trump and said he would turn in his season tickets and boycott games.
Cuban's response? "DM me and I'll help get it done."
"The way I read it was that if you don't want to be a season ticket holder, I don't want you to be one," Zaccanelli said, suggesting that Cuban's political platform has been a drag on his businesses, particularly his pro-basketball team.
But Cuban disputed the assertion.
"For every hate email there was a positive one as well," he said of the response to his political opining, adding that he didn't see his politics becoming a drag on the Mavericks because "remember, Clinton won Dallas County."
A recent poll showed that the split sentiment in Cuban's inbox could be indicative of a larger one. The results of that poll, conducted by the left-leaning Public Policy Polling, found that Cuban would be in a neck-and-neck race against the sitting president in a prospective one-on-one 2020 election.
Tom Jensen, the pollster, said Cuban proved to be "pretty competitive given his comparatively low level of name recognition at this point."
'He needs to hire someone to help create the entire campaign'
For Cuban to have a serious chance at securing the White House, he would need to start taking policy positions and filling out the bare bones of a campaign infrastructure soon, campaign experts told Business Insider.
And unlike Trump, Cuban would have to run more of a "traditional campaign," said Terry Sullivan, Marco Rubio's 2016 presidential campaign manager.
"He definitely comes across as a more cerebral and thoughtful candidate than Donald Trump, and he's clearly got a better, self-made billionaire story," Sullivan told Business Insider. "But ... because of that, he's not willing to set his hair on fire to make news in the same way. So it makes it a little more difficult for him to cut through [the noise] than a Trump [type]."
The first steps to laying out a campaign infrastructure, Sullivan said, would be to get informed on the issues and begin to take positions on key areas of policy.
Cuban has already started to do that. He put forth a proposal to fix the Affordable Care Act, and he hammered away at a jobs platform heavily focused on dealing with what he sees as an upcoming wave of job loss due to automation, necessitating "macro"-level changes to economic policies.
Should he decide to run, Cuban will also need to address what the future of his business empire would look like — something he said he has already considered.
"I have so many private business investments that it would be impossible to sell them," Cuban told Business Insider. "I would put them in a blind trust but make it clear I would still be available on a limited basis for those companies. It wouldn't be fair to those companies if I just bailed on them.
"I would also be very transparent," he went on, seeming to take a jab at Trump, who has come under fire from ethics experts who have said Trump has not come close to fully complying with conflicts-of-interest laws and severing his business interests. "Truly transparent about what I was doing. And yes, I would make my returns available."
Sullivan said the next step would be to "get the media's attention that you're a serious candidate." He suggested Cuban start traveling to states like Iowa to hint he may be serious about getting in the fray.
"The amount of attention he would draw by doing a Lincoln Dinner in Davenport, Iowa, would be huge," Sullivan said. "Those are the kind of things he has to start with."
Sullivan added that Cuban should "absolutely" hire a team of political advisers to develop a long-term strategy for him if he is sincerely interested in pursuing the White House.
Cuban, Sullivan said, should also "start at the top" and find someone, preferably with experience, who could manage his campaign. From there, he could consult that person to make other hires.
"You reach out to people who've done it before," Sullivan said. "I mean, he shouldn't be out there worrying about hiring — I'm going to hire a press person here or a TV guy here or a policy guy here. He needs to hire someone to help create the entire campaign."
The core team would also have to come up with a plan for victory. At this stage, Sullivan said it isn't clear whether Cuban would be better off running as an independent or a Democrat.
Cuban is not registered with a political party, and he would have to commission additional polls to gather data to see what his best route would be at this early stage.
"Plus, it is so early in the Trump administration. You can start laying the groundwork on things you need to do, but it doesn't necessarily mean you need to make some clear decisions," Sullivan said. "You go into a more preliminary mode now, where you just put yourself in a position to succeed and then make commitments for closer in on how you're going to run."
Cuban seems content dishing out his takes on cable news and Twitter. But this isn't a long-term model for someone who's going to have to go a more traditional route, Sullivan said.
"Smart tactics are not necessarily smart strategy," he added.
Reed Galen, deputy campaign manager for Sen. John McCain's 2008 presidential campaign and California Gov. Arnold Schwarzenegger's 2006 reelection bid, told Business Insider that Cuban is going to have to figure out how much of his own money he wants to spend, which he suggested might need to be upwards of $500 million if he decides to run an independent presidential bid.
"He won't have the party apparatus helping raise money," said Galen, now the owner of Jedburghs, a political consultancy firm. "There would be people from both parties who would likely work for him. But the traditional networks that raise money for these people are at least initially out of bounds or unavailable. So how much of his own money is he willing to spend?"
Galen said Cuban needs to hire experts who have good political instincts and experience, can convince Cuban against pursuing a bad idea, and who understand that Cuban's campaign will have to be "unique to his style."
It's also a matter of figuring out who Cuban's base would be and where he would compete on the map. As an independent, he would need to run essentially a 50-state campaign, depending on his endgame. As a Democrat, the map would look slightly different. Ballot access would also be a huge question, and Galen said starting early on that would be essential to an independent bid.
"Who is the base for a candidate like Mark Cuban?" Galen asked. "A lot of research and a lot of work needs to go into that, because you've got to figure out who you've got to go talk to."
"What's the goal? Is the goal to get to 270? Or is the goal to get to a draw between the two major parties and an independent candidate and throw it to Congress? And what does that look like?"
Galen said that the states Cuban should most closely look to include Texas, where the strategist said he would likely have some home-state advantage, as well as some of the states where the past two presidential races were closely fought. Places like Pennsylvania, Colorado, Michigan, Arizona, Nevada, Minnesota, Wisconsin, and Florida should be key targets.
In states like those, Galen said Cuban could find himself carving out "30% in the middle," possibly enough to win in a plurality.
Cuban also needs to figure out exactly what his message is to "invigorate and bring together a very divided and ... nervous country," Galen said.
"How is he going to bring a very tribalistic political society?" he asked. "Republicans and Democrats. How're you going to start to peel off those people who have decided that the two-party system doesn't work anymore and are willing to take an independent as a legitimate choice."
Galen did acknowledge that Cuban "would be a fascinating addition to the presidential contenders list." He also provided Cuban with advice on what the absolutely first thing he should do is.
"What I'd have him do is read 'What It Takes' from Richard Ben Cramer," Galen said, referring to a book on the 1988 presidential election. "Because there is not going to be any better opus on what it means to run for president than that book.
"Short of doing it, of course."
'He thinks 10 moves ahead'
The idea that a Cuban candidacy is being chatted about among the political class is stunning to his lifelong friends.
Then again, so was the fact he became such a prominent surrogate for Clinton and inserted himself right in the middle of the heated 2016 discussion.
"It's hard to believe," said Todd Reidbord, the president of Pittsburgh-based Walnut Capital, who has been a close friend of Cuban's since the two grew up together in Mt. Lebanon, a prominent Pittsburgh suburb. "The whole thing is like a dream ... None of us could've ever predicted that. But that's Mark."
Reidbord described his friend as "unpredictable" and explained how he was "totally" shocked when Cuban was blasting Trump as a top Clinton surrogate, elevating himself in the political world in the process. When Cuban stumped for the Democratic presidential nominee in Pittsburgh, Reidbord was there to see it firsthand.
It would be surprising to Reidbord if Cuban decided to take that extra step and seek the presidency. But at this point, nothing really surprises Reidbord about his old pal anymore.
"Every time I've ever tried to guess what he's going to do next," he said, "I've never guessed right."
Stu Chaban, another longtime friend of Cuban from Mt. Lebanon, said he's confident the billionaire won't be shy about seeking the White House if it's something he genuinely desires.
"If it's the right thing for him and what he wants, he'll do it," Chaban said.
In a sense, Chaban said it's going to come down to one thing: timing.
Regardless, those who know him best expect that he's calculating his next moves.
"Mark is a chess player," Reidbord said. "He thinks 10 moves ahead. I'm not sure that Trump is thinking 10 moves ahead. Mark certainly is."
