Chapter 13, Part 5: Michael Bloomberg

Despite his praise of Trump, Martin Shkreli didn’t vote for the real estate mogul in the 2016 presidential election. But in 2020, he might have voted for Bloomberg if he could.

What does the world look like through the eyes of a self-made billionaire, I wonder. Maybe they believe, as Egyptian pharaohs did, that they are literal Gods — that humanity exists only to further their ambitions, and that everything they touch, whether it’s a business plan or a wad of toilet paper, is improved by the encounter. Maybe they feel extremely validated for all of their life choices. Every whim that tickles them must Signify Something Important. Every opinion their neurons generate must be an Incontrovertible Truth. 

Or, perhaps like the rest of us, they’re driven by ordinary human emotions and flaws like pride, vanity, insecurity and a yearning for attention, love and satisfaction. It just might take much more substantial, dramatic, and expensive acts to silence their inner critics and feel accomplished — whether it’s buying a superyacht with a private submarine and rooms covered  in stingray leather, taking over a social media platform, or running for president of the United States. Like us, they’re running a rat race. They’re just after a much, much bigger block of cheese.

Ego was probably the impetus behind Donald Trump’s run for president in 2016. Political analysts speculated that he hadn’t even been contemplating such a move – at least not seriously, as more than a publicity stunt – until then-President Barack Obama roasted him at the 2011 White House Correspondents’ Dinner. Comedian Seth Meyers, the host of the event, further called Trump’s rumored political interests “a joke.”

Not to be outdone by Trump, more a cartoonish caricature of a tycoon than a real one, an astute, competent and respected self-made New York billionaire stepped up to the plate in 2019: Michael Bloomberg. Maybe his operating assumption was that the only thing that stops a “bad” guy with a multi-billion dollar fortune in a battle for the free world is a “good” guy with a larger multi-billion dollar fortune. (Forbes currently estimates Trump’s worth at $2.5 billion and Bloomberg’s at $94.5 billion.)

The cover of Bloomberg’s autobiography.

In any event, it was possible that Bloomberg could have lured away the “pro-business” votes from Trump. I know he had at least one very devoted, well-known fan who had previously loudly supported Trump but would have happily stumped for the “good” billionaire instead (that is, if he weren’t locked up in prison at the time and viewed as an “untouchable” pariah by the entire political establishment): “Pharma Bro” Martin Shkreli.

While Martin Shkreli publicly proclaimed adoration of Trump in 2016, and even played part of the famous single-copy $2 million Wu-Tang Clan album over a live stream in celebration of Trump’s victory, he didn’t actually vote for the reality TV real estate mogul. Martin didn’t bother himself with voting in any election, presidential or otherwise. He despised politics and politicians in general. Had he been able to do so in 2020, however, he told me he might have made an exception for Bloomberg. 

Like many young entrepreneurs and financiers, Martin idolized Bloomberg. He had, after all, achieved..

… the capitalist American dream. While he wasn’t exactly born poor, he had risen breathtakingly far from his roots. Bloomberg had a sort of middling upbringing in the Boston area as the grandchild of Eastern European Jewish immigrants, and he got into excellent schools: Johns Hopkins University and Harvard Business School. He put what he learned to good use.

Bloomberg’s now enormous data, analytics and media company, making more than $12 billion in revenue a year, began with a “mere” $10 million investment, a severance check he had received after being fired in 1981 from investment firm Salomon Brothers. His eponymous computer terminals, vast repositories of financial information, were viewed as essential utilities on trading desks everywhere. 

When he was just a skinny, squirrely teenaged hustler, Martin met Bloomberg in person and begged him to sign a copy of the billionaire’s autobiography: “Bloomberg by Bloomberg.”  I was familiar with the book because it was given by the company to all new Bloomberg employees. Written with help from Bloomberg News’ longtime editor in chief Matthew Winkler, it had the same forthright, unadorned, and non-introspective style that its media operation espoused.

But while Martin did want Bloomberg to win, he also acknowledged the challenge would be formidable. “He is pretty out of touch IMO,” Martin wrote to me over the prison email system in January 2020. “With someone like that, people can’t advise him and just tell him he’s a stiff nerd that will never win.”

A discussion over prison email between Martin and me about Michael Bloomberg’s candidacy.

Martin liked that Bloomberg’s success was staked on results and not on being likeable. New Yorkers complained incessantly about him during his 12 years as mayor from 2002 through 2014. They found him cold, technocratic and impersonal. But they were evidently satisfied enough with his leadership to reelect him twice. 

Table of contents in Bloomberg’s autobiography.

Similarly, at his company, he commanded respect and maintained authority over his 19,000-person global workforce without doing anything remotely warm or fuzzy. In fact, I heard many anecdotes through colleagues about how cruel and unforgiving he could be. 

For instance, Bloomberg supposedly once came across one of his reporters leisurely reading a newspaper during work hours (an ordinary activity for journalists) and was so appalled by the appearance of laziness that he fired the man on the spot. Perhaps because of paranoia seeded by this type of story, Bloomberg reporters and editors usually tried to stay extremely busy, or at least look like they were, while in the company’s Manhattan headquarters.

Bloomberg insisted that his employees adapt to his workplace preferences and recipes for success. He tolerated no deviations. In the newsroom, he made reporters and editors sit “cheek by jowl” at long desks in a big open space, as if they were on a trading floor. Most of them hated the arrangement. They also hated his hyper-competitive management style, long described as being like “putting cats in a bag” and seeing which emerges as the winner. Teams and individual employees often felt pitted against each other.

But the workers usually stayed because they had high salaries, reasonable levels of job security, and excellent benefits, all rarities in the journalism business. And Bloomberg knew he could also buy their loyalty with special perks like a vast selection of free snacks and drinks (although the coffee was notoriously weak because Bloomberg liked it that way, colleagues groused to me).

Everything at the company carried his stamp, both literally and figuratively. The glass office tower at 59th Street and Lexington Avenue was outfitted to his specifications. In keeping with his philanthropic climate initiatives, the elevators stopped only at certain floors to conserve energy. Instead of plastic, the Bloomberg-branded cups and utensils in the employee snack areas were made of more environmentally-friendly vegetable starches.

It was impossible to believe that anything at his company operated outside of his influence. Even quitting, or never working there in the first place, wasn’t a sure way to evade his grasp. 

Confidentiality over even the most routine internal matters was paramount at Bloomberg, and that was worrisome to me given that I had left my job there to date a scandalous figure. Rumors were undoubtedly spreading about what happened, and someone was bound to break the story sooner or later. Who’s to say that Bloomberg wouldn’t intimidate me if I ever tried to explain myself publicly? 

Once after Bloomberg News mysteriously killed an investigation into Communist Party elites in China, the company silenced reporters involved through financial threats to prevent them from talking in the media about what happened. The company also pressured the wife of one reporter to sign a non-disclosure agreement. Even women who were alleged victims of sexual harassment at the company were bullied into keeping their mouths shut.

I carried a knot of anxiety in my stomach when I thought about what could be in store for me if I embarrassed the ninth wealthiest man in the world…especially while he was running for president. 

In theory, Bloomberg’s presidential run did make a certain amount of sense, and at the outset at least it didn’t seem impossible at all that he could win. He had a lot of the right ingredients: compelling business credentials (more so than Trump’s, anyway), government leadership experience, and a track-record as a left-leaning centrist, matching a wide swath of the country’s socially liberal and fiscally moderate views. 

Financed with an almost bottomless war chest of his own resources, Bloomberg’s campaign took off like the Titantic in November 2019 – seemingly unsinkable. But it met a similarly swift and disastrous end. His iceberg was Sen. Elizabeth Warren, another contender for the Democratic nomination. 

In his first televised primary debate in February 2020 (he participated in only two before dropping out), Warren laid into Bloomberg over past sexual harassment claims at the company and allegations that he, himself, had made crude and sexist remarks to women who worked for him. She also attacked him on the obvious grounds that he was a billionaire who was trying to buy the presidency by funding his own campaign.

As he stumbled, she clamped down harder. She took aim at the non-disclosure agreements his company had brandished, menacingly, against former employees – including those who were alleged victims of harassment. His attempts to recover his composure, explain himself, or try to suddenly shift his position by releasing some of the women from the NDAs went nowhere.

His campaign limped along for a few weeks after that, but the momentum was gone. Warren had inflicted a death blow. Ironically, his efforts to protect his public image, through aggressive NDAs, had ended up hurting his public image.

I watched the debate in horrified fascination, wincing on behalf of my former boss as Warren’s attacks drew blood and his dream evaporated.

But I also felt a stirring of relief. Bloomberg looked so humiliated over the whole mess with the NDAs that I couldn’t imagine him trying to silence former employees again. The wheels in my head started to turn, and I began to strategize seriously about coming forward and talking in the media about my relationship with Martin. My biggest fear was neutralized.