It takes some preparation before Monopoly Man can appear and twirl their mustache for the cameras. For a little more than a year, they've periodically taken over C-SPAN and political Twitter, dressing up as Rich Uncle Pennybags from the classic board game Monopoly. With a top hat and a fake bag of money, they've quietly photobombed the likes of Richard Smith, the former chief executive of Equifax, and Mick Mulvaney, then the acting Consumer Financial Protection Bureau boss, as they testify before lawmakers. While the speakers drone on about their good intentions or latest policy initiatives, Monopoly Man sits just over their shoulder, adjusting a monocle or brandishing a faux $100 bill.
Despite their popularity, Monopoly Man — played by Ian Madrigal, a strategy director at Revolution Messaging, a progressive digital media firm — has retained a Clark Kent-level of anonymity, even while maintaining a fashion blog, Queer on Clearance, that once chronicled the price and origin of each piece of the Monopoly Man “drag costume.” Madrigal, who is transgender and stands 5 feet 9 out of costume, with short brown hair and glasses, makes the stunt look like a lark. But it is really an elaborate act of protest: a combination of entertainment and trolling that Madrigal calls “cause-play.”
One morning in December, I visit Madrigal’s Capitol Hill apartment to see what goes into a Monopoly Man appearance. Today’s hearing at the House Judiciary Committee features Google chief executive Sundar Pichai, who will try to address lawmakers’ concerns over privacy, the company’s purported anti-conservative bias and its plans to relaunch in China.
“The issue for me is to show that this guy” — Pichai — “is not their friend,” Madrigal explains while munching on a bowl of Trader Joe’s Very Berry Clusters cereal. “There’s a lot to protest,” they say, including Google’s use of forced arbitration and allegations of racial discrimination within the company. “Here I can steal a little bit of the spotlight.”
Soon, it’s time to get dressed. Madrigal, already in a suit, puts on a red bow tie before throwing fake mustaches, several monocles and other accessories into a satchel. As Monopoly Man, they employ the exaggerated mannerisms of a silent-film comedian. When the person testifying says something outlandish, Monopoly Man might arch an eyebrow and raise a monocle to their right eye. Madrigal may also lift a bag of bogus money into their lap and thumb through its contents. “Surprisingly I’ve never been arrested for anything I’ve done,” they say, slipping $50 into their wallet for bail just in case, before we head out the door. “It’s like a white person superpower.”
Madrigal, 29, has had a troublemaking streak since their childhood in Lakewood, Calif., just outside Long Beach, where their father, now retired, worked industrial sales jobs and managed a scrap metal yard, and their mother is still a legal secretary. Born Amanda Werner, a name they used until late 2018, Madrigal was 3 when they told their mother they were a boy ("It may have led to some boldness or brashness with Monopoly Man; I'm not easily embarrassed") and 14 when they experienced a "political awakening" while listening to the punk rock band Anti-Flag.
Their family was conservative — both parents voted for Trump in 2016, Madrigal says — and few of their friends talked politics. But Madrigal was soon picketing a nearby Disney Store over allegations that its clothes were made in sweatshops. Law school at UCLA led to a job as a legal fellow for Sen. Elizabeth Warren (D-Mass.), and to a position at the consumer rights advocacy group Public Citizen, where a co-worker suggested that someone dress as Monopoly Man. Madrigal, who had appeared in improv comedy videos in high school, volunteered; they proposed appearing at hearings as a way to draw attention to Public Citizen’s campaign against forced arbitration, in which employees or consumers are required to waive their right to a class-action lawsuit. (Madrigal currently appears as Monopoly Man outside of their job at Revolution Messaging.)
Madrigal assembled a costume from clearance racks and Amazon vendors. “I consider it using one billionaire” — Amazon chief executive Jeffrey P. Bezos, who also owns The Washington Post — “to fight a different billionaire,” they note. “Hopefully it all evens out.”
Monopoly Man first showed up in October 2017, at Smith’s Equifax hearing, and has since made three more appearances at congressional hearings. Madrigal has also tried out another character, appearing at Facebook chief executive Mark Zuckerberg’s April Senate hearing dressed as a flame-haired “Russian troll doll” — but Monopoly Man is a crowd favorite. “I thought it’d be a funny idea, maybe turn into a BuzzFeed article. But I didn’t know it’d blow up like this,” Madrigal says. Jeff Flake, then a Republican senator from Arizona, tweeted about Monopoly Man (“Well, Rich Uncle Pennybags is back in my Committee hearing”). Madrigal’s Ask Me Anything thread on Reddit is the site’s 10th most popular AMA. And Fine Brothers, a media company that makes content for YouTube, has partnered with Madrigal to pitch a TV show on creative political campaigns, framed as a kind of “Queer Eye” for activists. “I think the only reason I haven’t gotten a cease-and-desist letter from Hasbro,” Madrigal says, “is I’m good for the brand.”
For the Google hearing, a professional line-stander arrives at Rayburn House Office Building Room 2141 around 4 a.m. to secure a spot for Madrigal. A few minutes before 10 a.m., Monopoly Man enters and sits in the center of the third row. I take a seat next to them. The gallery fills quickly, and we’re soon joined by a group from Amnesty International; an activist for the repressed Uighur minority of western China; and the general counsel for DuckDuckGo, a Google rival. Seated near the back are Trump adviser Roger Stone and Infowars’ Alex Jones, both of whom claim they have been censored by the search engine.
“This is the part where my heart starts to pound a lot,” Madrigal whispers, carefully applying a fake mustache. “Is it straight? All right, let’s go.” The monocle is raised, and House Majority Leader Kevin McCarthy (R-Calif.) opens the proceedings by thanking Pichai for his time. “Google must not be tracking all our movements, because they certainly didn’t see me coming!” Madrigal tweets. Screen shots on Twitter show Madrigal front and center on C-SPAN3, just over Pichai’s left shoulder.
The hearing lasts 3½ hours, during which Monopoly Man alternates between tweeting (“We can’t rely on tech giants to self-regulate. It is past time for Congress to step in and do its job”), taking selfies, and performing. Eventually, Madrigal’s mustaches proliferate: They put a second on their hat, then a third; a fourth goes atop their monocle. “I have more mustaches than Google has competitors,” they tweet.
When the hearing adjourns, Monopoly Man tries, unsuccessfully, to offer Pichai a Get Out of Jail Free card. Fox Business Network’s “Varney & Co.” sends them a Twitter message about coming on the show. Co-workers at Revolution Messaging send support through Slack. “Twitter seems to be buzzy,” Madrigal says, before taking off the bow tie. Their back aches. “I’m always so eager to get out of costume.”
Harrison Smith is a Post obituary writer.