When life in prison is not long enough

Silk Road founder Ross Ulbricht just had to spend his eighth Christmas behind bars. On this occasion, I want to take a look at other crypto-related people who are currently serving long prison sentences.

German version

At the end of 2020, I published a c’t article about Ross Ulbricht, the former operator of the illegal online trading platform Silk Road.

Quelle/Source: Schmeh

Ulbricht (born 1984) was sentenced in 2015 by a U.S. court to two life terms plus 40 years.


Ross Ulbricht

Particularly harsh: Ulbricht’s sentence was pronounced “Life without Parole” (LWP). This means that the convict cannot be paroled early. Only the US president can pardon him.

Quelle/Source: Lyn Ulbricht

For the article, I conducted an interview with Ulbricht’s mother Lyn (on the left in the picture, on the right his sister), which was not printed in c’t due to space limitations:

Klaus: Can you tell us briefly how is Ross doing today?
Lyn: Ross is staying strong. He is a very positive person and always takes the high ground. See his essay on Five Keys to Inner Strength I Learned in Five Years in Prison.

Klaus: What are you doing in order to get Ross out of prison?
Lyn: We need to convince President Trump to commute Ross’ sentence and we need to get his attention. One way is the clemency petition, which now has over 1/4 million signers and is the second largest clemency petition on Change.org. You don’t have to be American to sign it, this is a worldwide effort, so we hope people in Germany will help. Ross supporters are also going to Trump rallies to get his attention for Ross.

Klaus: Can you tell us about your and Ross’ social media activities (e.g., on Facebook and Twitter)?
Lyn: Ross sends his messages by mail to someone close to the family and they post for him. They are all Ross’ words. It is a good way to get a sense of who Ross really is and it lets him communicate.

Klaus: The surname “Ulbricht” sounds German. Does Ross have ancestors from Germany?
Lyn: Yes, Ross’s German ancestors were from Dresden and immigrated to Texas in the 1820s. They were Henry and Herman Ulbricht, two brothers who came to America together.

Klaus: What can people in Germany do to support Ross?
Lyn: Sign and share the petition, donate to our Freedom Fund, spread the word on social media, or help us directly. People can contact us at info@freeross.org.

Klaus: While many Germans criticize the USA for still having the death penalty, most of them are not aware of the wide-spread “life without parole” punishment in the United States. Do you think politicians, the press, and human rights groups in Germany should pay more attention of this topic?
Lyn: Yes, because as Ross says, it is a death sentence. It just takes longer.

For the new year, I received the latest issue of a newsletter that Lyn Ulbricht and a few followers send out regularly.

Quelle/Source: FreeRoss.org

The Ross Ulbricht case once again highlights the numerous absurdities in the US legal system. It is strange, for example, that Ulbricht’s quasi-successor Blake Benthall, who operated Silk Road 2 in a similar form and with greater turnover, went virtually unpunished. The reason for this is probably that the U.S. authorities found the expense of a trial too great and preferred to use Benthall as a witness against others.

So far nobody could tell me how often it happens that a US president pardons a “life-without-parole” prisoner – even Ross Ulbricht’s mother did not know this. I have been able to locate only one such case at all, which is not hopeful given the number of such rulings.


Brian Regan

The Ulbricht newsletter was an occasion for me to consider which crypto-relevant people are currently serving longer prison sentences in the USA. The first person that comes to mind is Brian Regan, who was convicted of attempted espionage. He used various encryption methods, some of which presented the FBI with some problems.

Quelle/Source: Wikimedia Commons

For information on Brian Regan and his encryption methods, see this Focus Online article of mine and the highly readable book The Spy Who Couldn’t Spell by Yudhijit Bhattacharjee.

Brian Regan was arrested in 2001 and has just spent his 20th Christmas in prison. Unlike Ross Ulbricht, he has no supporters running a website or collecting signatures for his pardon.

Regan was also sentenced to “Life without Parole,” so he can expect to spend the rest of his life in prison. His (failed) attempt to sell state secrets to Libya or Iraq was plenty stupid, but I still think the punishment is too harsh.


Robert Hanssen

Unlike would-be spy Brian Regan, Robert Hanssen (born 1944) did enormous damage as a traitor to secrets. For 22 years, the FBI employee and counterintelligence specialist sold classified information to Russian intelligence, delivering numerous U.S. agents to the knife. For this, Hanssen collected $1.4 million and an undisclosed number of diamonds.

As a practicing Catholic and family man, Hanssen aroused no suspicion for a long time, especially since he acted very cautiously and used the large amount of money he received sparingly. In 2001, however, he was finally exposed. His arrest is captured on a short video:

Hanssen was sentenced to 15 years to life in prison (also “Life without Parole”). Prior to his arrest, FBI investigators managed to decode encrypted data on Hanssen’s handheld computer, which provided important evidence.

I find it strange that Robert Hanssen has to serve his sentence in the notorious maximum security prison in Florence (Colorado). This is where violent criminals and gang members are imprisoned. Perhaps this measure was intended to additionally humiliate the spy.


Harold Nicholson

In the same prison as Hanssen is spy Harold Nicholson, although he too has never been noted as violent. I blogged about Nicholson’s encrypted postcards in 2016.

Quelle/Source: Wikimedia Commons

Compared to other spies, Nicholson was lucky – he got off with a 23-year prison sentence. He is due to be released in November 2023.


Ted Kaczynski

Another inmate of the maximum security prison in Florence is Ted Kaczynski, better known as the Unabomber. Between 1978 and 1995, Kaczynski mailed numerous package bombs, killing three people and injuring 23. In 1998, he was sentenced to life in prison (“Life without Parole”).

Quelle/Source: Wikimedia Commons

I blogged about Kaczinski’s encryption method in 2016. Kaczinski was a respected mathematician before his career as a criminal, which is evident in his ciphers. Kaczinski learned German fluently at Harvard University, which he uses for letter contacts with German speakers.

The meanwhile 78-year-old Unabomber can probably not count on a pardon. To this day, he has shown no remorse.

If you want to add a comment, you need to add it to the German version here.

Further reading: Zwei US-Spione werden nach 30 Jahren aus dem Gefängnis entlassen

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