Chapter 13, Part 4: Columbus & Picasso
Famous men were usually jerks, but did they have to be? That was a complicated conversation to have with Martin Shkreli.
A complicating factor when it comes to understanding “problematic” men is the realization that just about all famous men throughout history were in one way or another “problematic.” I’m not talking necessarily about sexual harassment here but more broadly about characteristics associated with “toxic males,” the likes of which regularly provoke bouts of feminist outrage on Twitter.
Cozy in my bed one evening, while reading a description of Christopher Columbus in a nonfiction book by author Patrick Wyman, I burst out laughing. I couldn’t help myself. It just landed far too close to the modern “toxic man” and specifically the business villain whose intersection with my life gave rise to this memoir. Columbus and Martin Shkreli were apparently both scrappy hustlers with giant chips on their shoulders, deep insecurity complexes, and blind spots for their own mistakes and shortcomings.
“Columbus was defined by a sense of burning ambition at every stage of his life,” Wyman wrote in “The Verge,” a bestselling examination of the beginnings of the Age of Exploration in Western Europe. The seafarer was “deeply ashamed of his humble background and actively obscured it whenever possible” and he was “determined to leave his origins far behind.” (That ticked a box for Martin.)
The explorer’s “overwhelming drive for success often bled into self-aggrandizement. He could be insufferable, boastful, and boorish, with precious little awareness of his many faults and weaknesses…At the same time, however, Columbus was a highly skilled sailor and possessed at least some measure of real charisma. He had raw mental gifts and was described by a friend as having “great intellect but little education.” (Those traits ticked boxes, too, minus the sailing.)
Columbus’s “ambition could express itself in arrogant and ill-planned sililoquies about his greatness,” Wyman continued, adding that the king of Portugal got an earful when Columbus returned successfully (sort of) from the voyage said king declined to support. Anyone who has watched Martin Shkreli’s live streams or witnessed him giving a press conference would have been treated to remarkably similar-sounding monologues.

One could argue that Martin’s biggest “accomplishments” — namely jacking up drug prices, getting convicted of securities fraud, making himself a household, if vastly despised, name, and dating a journalist who broke the story of his arrest (me) — are really just all supernova-like disasters. Meanwhile, Columbus actually did something brave, important, and good by sailing across the Atlantic, right? Or did he?
It’s taken many years, but we now collectively recognize the dark side of Columbus’s adventures and the great harm he caused. He personally brutalized and enslaved possibly tens of thousands of natives, and the diseases he and his comrades brought with them to the New World caused even further devastation. His violent administrative tactics were so terrible even other Europeans found them appalling, and Spanish authorities stripped him of his governorship of the islands he had “discovered” (which he still erroneously thought were in Asia).
He also opened the door for further European incursion, eventually leading to white settlers taking over the Western hemisphere and committing widespread genocide. But Columbus lived at a time when a lot of men were tempted to seek out riches by setting off on foolhardy missions and looking for spices, gold, slaves, and anything else they could exploit for profit. Europeans invading, infesting, and plundering the Americas was likely inevitable, whether it was Columbus who carved the path or someone else.
Accounting for cultural differences, I can imagine Columbus’s explanations for why he engaged in so much cruelty probably would have sounded similar to Martin’s for raising the price of Daraprim: “It was an opportunity there for the taking. If I didn’t, someone else would. Hate the game, not the player.” Whatever delusional self-confidence it took for a sailor in the 15th Century to convince a monarch to finance an expedition into the unknown, under crude assumptions about the size of the Earth and where the ships would end up (not India), Martin certainly had some of that, too.
I had never heard Martin praise Columbus. But he did idolize many later business titans and other famous men who displayed the same brand of alpha male swagger as European explorers. In his aforementioned live stream monologues, he sometimes compared himself to people like John D. Rockefeller, Andrew Carnegie, Steve Jobs, Bill Gates, Warren Buffett, and Michael Bloomberg. Perhaps not coincidentally, his heroes were rarely known for being “nice” guys; more often, at least before making their fortunes and becoming philanthropists, they were known for being jerks.
Perhaps that was partly why Martin didn’t mind being perceived as a jerk – in his view, such characteristics went hand-in-hand with success. He took the term as a compliment.
I think Martin was right about the correlation. The same qualities which enticed entrepreneurs, explorers, and other famous figures throughout history to take bold risks probably came packaged with being brash, difficult, arrogant, sometimes abusive, and often womanizing. But did the negative attributes cause success, as Martin assumed? I wasn’t so sure. To me, toxic personality traits often seemed to limit or undo whatever good “alphas” did manage to pull off.
Although Martin assumed accomplished men were usually jerks, he wasn’t always comfortable when books, movies, or other media delved deeply into their jerk-like tendencies. He grumbled especially at tell-all exposés from wives and girlfriends, or other “secondary” characters behind the scenes, providing a less-than-flattering look into the men’s personal lives. Maybe he felt vulnerable to similar treatment from me.
For instance, Martin was bothered a bit by artist Françoise Gilot’s memoir “Life with Picasso,” her telling of her May-December romance with the great painter when she was in her 20s and he was in his 60s. She wrote the book after they split up, and Picasso filed three lawsuits to try to keep her from publishing it. Their relationship, at least to Gilot, had a lot to do with intellect and appreciation of art. She became a well-known painter, too, although always in Picasso’s shadow.
Considered a pioneering innovator of modern techniques, Picasso was possibly the most famous and influential artist of the 20th Century. He was also massively prolific. Over his nearly 80-year career starting in the 1900s, he is thought to have created as many as 13,500 paintings, 300 sculptures, 34,000 illustrations, and 100,000 prints and engravings.
While his most famous works such as Guernica or The Old Guitarist might be valued at hundreds of millions of dollars or more, the sheer number of Picassos means that there are some at relatively affordable price points for the up-and-coming elites who want to engage in conspicuous consumption. Wall Streeters are fond of collecting Picassos. Martin Shkreli even acquired a Picasso engraving at a high point in his career. He described it later on in the press, amid federal prosecutors’ attempts to seize it, as “low-dollar.”
Gilot’s straightforward memoir offers a detailed perspective of Picasso’s work while also showing that he was more often brittle and dismissive toward her and her talents than encouraging or supportive. A reviewer for NPR wrote that her story is “without fail warm and empathetic” but “Picasso emerges as domineering, sexist, and borderline abusive.”
As the reviewer continues, she notes that Picasso “tells [Gilot] frequently that ‘there are only two kinds of women – goddesses and doormats.’ But Gilot is neither. She is never a victim or an ingénue. In ‘Life with Picasso,’ she is a highly intelligent young artist to whom her former lover’s artwork is as intellectually exciting as their relationship was destructive.”
Appearing all the more monstrous, Picasso sneers at Gilot and her ambitions at the end of the book, telling her: “You imagine people will be interested in you?...Even if you think people like you, it will only be a kind of curiosity they will have about a person whose life has touched mine.”
Chillingly, Picasso wasn’t wrong. On Wikipedia, the first line of the entry for Françoise Gilot reads that she “is a French painter, best known for her relationship with Pablo Picasso, with whom she had two children.” Try as she might to establish a career for herself and be judged on her own merits, society wasn’t going to let her have that. As gifted as she was, she would forever be “Picasso’s girlfriend.”
At first, Martin was fascinated by the book. He wrote an email to me from prison talking about how it was a “decent discourse on romantic interactions between men & women.”
“Picasso is enthralled by this woman and keeps trying to seduce her,” he added. “She gets that and plays along but resists just firmly enough to keep it interesting.”
Later on, though, his feelings on the book soured. He later told me that he didn’t really enjoy reading it after all, and that he thought Gilot was just using Picasso as a launching pad for herself.
Perhaps it all hit just a little too close to home for Martin, who had already agreed to let me write a book about him well before we started “dating,” or so one might call it, while he was in prison. Would I be seen like Gilot, always an adjunct of a man – in this case Martin? Did he want that either for me or himself? I suspected not.
I think he was also probably grappling with the full understanding that he could not control what I would say. If things did end badly, that would be in my book.