Donald Trump is again making promises to constituents that he may or may not keep, believing it's politically expedient to tell some libertarian crypto bros that he would pardon Silk Road founder Ross Ulbricht if he became president again.

Setting aside the fact that someone must have just told Trump about Ulbricht recently — he's been in jail since 2013, and Trump already had a chance to pardon him during his term as president — this could be a problematic pardon for any number of reasons. Ulbricht was a hero to some for being a pioneer on the lawless dark web, making one of the early Bitcoin fortunes by setting up an online black market. But things took a sinister turn as well, involving the hiring of a hit man.

As the Chronicle reports, Trump has gathered that the campaign to free Ulbricht has some cachet among anti-government types, even though Silk Road was largely just a drug marketplace, and Trump is anti-drugs. Not to mention it was just a precursor to the ongoing, decentralized world of the dark web, which is also a haven for identity thieves and would-be terrorists — like former Newsom associate Ryan Chamberlain, who was arrested in SF after seeking bomb-making materials and lethal toxins on a Tor site just like Silk Road in 2014.

Trump told a convention of libertarians earlier this year that he'd free Ulbricht "on Day One," and he's continued to say this when talking to groups who know who Ulbricht is. So much for people bringing drugs and weapons into the country from the southern border — let's celebrate the circulation of drugs and weaspons on the dark web and pardon one of its pioneers!

It was one of the bigger SF stories of 2013 when a then-29-year-old Ross Ulbricht was arrested at a branch library by FBI agents and charged with a litany of crimes in connection with the black-market site known as Silk Road.

The arrest happened on October 1, 2013 at the Glen Park branch library, and until then, users of Silk Road and law enforcement only knew the proprietor's name as "Dread Pirate Roberts" — a reference to The Princess Bride. The arrest itself was the stuff of cinema, and indeed the story was turned into a 2021 movie that no one saw. Two agents reportedly staged a fight in order to distract Ulbricht, while a third agent snatched his laptop so they could access its files before he could lock it.

While it was operational, Silk Road was a go-to spot for procuring molly and other drugs, and it was an early adopter of Bitcoin, back in the day when one Bitcoin was trading for around $100 (in early 2013 it was actually closer to $10). But Ulbricht wasn't just creating a libertarian dream marketplace beyond the reach of law enforcement. Things became messy, and more violently criminal, when Ulbricht paid someone claiming to be a Hells Angel $150,000 to killed a Silk Road user who had been threatening to expose other users of the site.

In addition to using a Tor browser, Ulbricht had been doing his Silk Road admin work from public wifi networks like libraries to further avoid detection, but the feds soon homed in on his location. And the laptop proved to be all the evidence they needed.

After the case moved to New York, Ulbricht was found guilty on all counts in February 2015. He was convicted on charges of trafficking drugs on the internet, narcotics-trafficking conspiracy, running a continuing criminal enterprise, computer-hacking conspiracy, and money-laundering conspiracy. And, a few months later, when Ulbricht was just 31 years old, he was sentenced to life in prison.

Though Ulbricht did make considerable money running Silk Road — enough that he'd pay someone $150,000 to kill a person — he wrote a letter to the judge in the case seeking leniency, which the judge would later call an act of "arrogance." In the letter, Ulbricht claimed he didn't have a profit motive, but instead was making a political point, and saying that “people should have the right to buy and sell whatever they wanted so long as they weren’t hurting anyone else."

Pretty sure hiring Hells Angels hit men constitutes wanting to hurt someone else.

And, unfortunately for the feds, their prosecution of Ulbricht did nothing to stop the growth of the dark web or its ongoing use as a marketplace for illegal goods. And there were even a couple of federal agents on the Silk Road case who were later charged with pilfering Bitcoin for themselves.

And what ever happened with all of Ulbricht's Bitcoin, which he was asking to get back from the government? He said he had 144,336 Bitcoins at the time, in late 2013, which was then worth about $100 million, and now would be worth $8.8 billion. Is that just sitting in a wallet on an 11-year-old laptop at an FBI headquarters somewhere, or...?

Previously: Ross Ulbricht, Accused Silk Road Founder, Was An Eagle Scout And Avowed Libertarian