Before a big physics final at the University of Texas at Dallas, two students blew off steam by playing a racquetball match. The students, both male, agreed the loser would wear a dress to the exam.
As he recalled, Jaspreet Sidhu defeated his best friend and roommate, Ross Ulbricht, in the match. That was in 2005, well before the FBI arrested Ulbricht in a San Francisco library on Oct. 1 of this year. Ulbricht is accused of running Silk Road, an online marketplace for all measure of drugs and other contraband, under the alias "Dread Pirate Roberts." Silk Road facilitated more than $1 billion in transactions during its two-and-a-half year existence, according to court documents, before the FBI seized the site the same day as Ulbricht's arrest.
See also: The Silk Road Online Drug Marketplace by the Numbers
Both now 29 years old, Sidhu and Ulbricht have fallen out of touch. Sidhu estimated the last time they saw each other was in 2011. For a period of several years, however, Sidhu said he and Ulbricht "were as tight-knit as people can be." In a video call interview with Mashable, Sidhu described Ulbricht, the supposed kingpin of the dark web, as a good-natured and carefree hippie, for whom "bathing was optional."
After losing the racquetball bet, Ulbricht squeezed into a skin-tight dress he borrowed from his girlfriend, Sidhu said.
"He looked damn good in that dress," Sidhu recalled. "Ross didn't give a shit. Ross wore it with panache."
Sidhu, who was born in India and moved to the U.S. at age six, confirmed what many of us who've been following the Silk Road story suspected: Ulbricht wasn't particularly fond of wearing a shirt.
"He's a hippie. That's the best way I can describe him," Sidhu said. "Ross was the guy who had stinky feet, that wore shorts — a shirt if you were lucky."
Ulbricht's recent San Francisco roommates, who know him as "Josh," told Forbes that Ulbricht "often walked around without a shirt." A woman from Texas, who said she met Ulbricht through OKCupid, wrote that he "weirdly took his shirt off" before drunkenly passing out at the end of their first (and only) date. Sidhu said Ulbricht would often show up at class with his shirt around his waist, at which point the professor would make him put it on.
Sidhu is pictured, below, with the shirtless Ulbricht in Facebook photos from 2006.

"Still the one at the party who takes their clothes off, I see," a commentator wrote.
Aside from Ulbricht's sartorial and grooming habits, Sidhu spoke highly of his former friend's character: "Ross is a good person," was a common refrain throughout our conversation.
Sidhu said he and Ulbricht roomed together with another friend and fellow physics major, Vikram Patel, for two years at the University of Texas dormitories known as the Waterview Park Apartments. Ulbricht attended the school from 2002 to 2006, according to his LinkedIn profile. Patel did not respond to our interview request.
Sidhu described himself as a "big tech junkie." He said he was aware of Silk Road before Ulbricht's arrest, as well as the digital privacy-protecting tools upon which the site relied, but he never used the site to buy drugs. Silk Road was only accessible using Tor, a software that allows for anonymous Internet browsing. Vendors and buyers conducted transactions using the difficult-to-track digital currency Bitcoin.
See also: Despite FBI Bust, Top Silk Road Drug Dealer Lives On
"It just caught me from left field, as I'm sure it caught everyone else," Sidhu said, referring to Ulbricht's arrest.
Several times throughout our conversation, Sidhu said the phrase, "Good people make bad choices." Even so, he said he still believes Ulbricht is innocent, particularly regarding the allegations that Ulbricht solicited murder-for-hire. According to FBI documents, Ulbricht twice offered to pay for the killing of rivals — once to protect the identities of Silk Road users and the other time to silence a compromised former employee.
"He's one of the kindest and most good-natured people I know," Sidhu said, referring to Ulbricht. "He loves animals. He loves nature."
But did he love The Princess Bride? Silk Road's owner, whoever that may be, borrowed his or her persona from the 1980s Rob Reiner-directed comedy based on a book of the same name. The story's main character, a genial farm boy named Wesley, transforms into a masked swashbuckler and inherits the feared title of "Dread Pirate Roberts" when the previous one decided to retire.
Sidhu said he doesn't recall Ulbricht mentioning the movie, but the two were big fans of the genre. Ulbricht "could reference any Monty Python movie ever made," Sidhu recalled, and he also enjoyed Mel Brooks films such as Blazing Saddles.
Although Ulbricht was easygoing most of the time, Sidhu recalled that he was very strong-minded when it came to politics and economics. Sidhu called him a "staunch libertarian and Green Party supporter."
Ulbricht's political willfulness is apparent through some of his social media profiles. On his LinkedIn bio, he wrote, "The most widespread and systemic use of force is amongst institutions and governments." In a July 5, 2010, Facebook note, Ulbricht posted a short manifesto titled "Thoughts on FREEDOM."
On Silk Road's forums, Dread Pirate Roberts was interested in political and economic philosophy. He even started "DPR's Book Club," a weekly discussion of selected reading materials. Here's a description of the book club from Dread Pirate Robert's introductory post on Aug. 14, 2012.
We will focus on agorism, counter-economics, anarcho-capitalism, austrian economics, political philosophy, freedom issues and related topics. My hope is that through this, we will discover what we stand for and foster a culture of peace, prosperity, justice and freedom. There is so much double-speak and misinformation in the world today that we must take our education into our own hands, and defend our minds with reason and critical thinking.
Another of Ulbricht's defining characteristics, according to Sidhu, is his intellect. Sidhu said Ulbricht flourished when the former helped the latter secure an internship at the University of Texas' NanoTech Institute.
"Whatever he put his mind to, if you could get him focused and passionate about, the man would complete no matter what ," Sidhu said.
After getting his bachelor's degree in physics, Ulbricht went on to study material science and engineering at Penn State. His 62-page graduate thesis is available online, and his work was published in peer-reviewed journals five times, according to his LinkedIn profile.
Darrell Schlom, who is listed as Ulbricht's thesis advisor and is currently a professor at Cornell University, declined to comment for this story.
It wasn't all science for Ulbricht. He listed himself as an "investment advisor and entrepreneur" on LinkedIn. Sidhu said he invested money with Ulbricht at one point, but he didn't gain or lose much. Sidhu estimated he came out a few hundred dollars ahead on a $10,000 investment, although he could not recall any specific details of the venture.
After making what it called the largest-ever Bitcoin seizure last week, the FBI said it now has collected 173,991 Bitcoin (equal to about $35 million) in connection with Silk Road.
The FBI estimates Dread Pirate Roberts collected $80 million in commissions. In his only interview before the site was closed, Dread Pirate Roberts told Forbes that he reinvested the “vast majority” of the site's profits.
Ulbricht appeared in federal court in San Francisco on Oct. 9. His public defender denied all charges and agreed to have Ulbricht extradited to New York City. Ulbricht's newly hired defense attorney, Joshua Dratel, told Mashable in an email that he is not yet sure when Ulbricht will appear in court.
"Ross Ulbricht maintains his innocence of all the charges against him. The government's —and to a considerable extent — the media's portrayal of him thus far is not accurate," Dratel wrote. "We will address all of that in the most important forum for Ross, which for the time being is in the courts, where evidence and not merely accusation is what counts."
Through it all, Sidhu said his feelings about his once best friend have never wavered.
"I love the man. I love Ross Ulbricht," Sidhu said. "He is family to me just as much as my blood and kin are."
Sidhu has not reached out to Ulbricht's family or Ulbricht himself since the arrest, but he plans to contact them. He also said he will travel to New York, or wherever Ulbricht stands trial, to support his friend in person.
Images: Google+, Ross Ulbricht, and Facebook, Ross Ulbricht