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.

AP Photo/Evan Vucci

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.”

Jonathan Bachman/Getty Images

“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.

Lucy Nicholson/Reuters

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.”