That said, I do think he absolutely deserved to be released, not because he didn't deserve to be locked up in the first place, but because he's clearly been rehabilitated and has done great work during his time in prison. All that considered, ten years seems like a not unreasonable prison sentence for what he did. I hope he'll continue to do good when he's released.
The guy operated a marketplace for illegal goods in order to enrich himself. The illegality wasn't just incidental, it was literally his business model -- by flouting the law, he enjoyed massive market benefit (minimal competition, lack of regulation, high margins etc) by exploiting the arbitrage that the rest of us follow the rules.
Said a different way, he knowingly pursued enormous risk in order to achieve outsized benefits, and ultimately his bet blew up on him -- we shouldn't have bailed him out.
A serial rapist, even one that would happily do it again, will often repent and quickly admit guilt. They have no interest in undermining the philosophical basis of the state. They will posture themselves as bound but imperfect citizens under the law.
Ross violated the only remaining national holy religion, the rule of law. He was sentenced for being a heretic.
Good.
Let's keep in mind that the shared faith in this "holy religion, the rule of law" is the only thing holding together your country, my country, everyone's countries, and civilized society in general. Take that away, and everything around us will collapse, regressing the few survivors of that event to the prehistorical lifestyle of small tribes slaughtering each other for what little scraps the land has to give.
The US also has laws which we don't care if you break, and the laws we place in this category say a lot about our society. For example, it's widely accepted that people can drive up to 10 MPH above the speed limit and consequences will be rare. Even more severe moving violations are met with a slap on the wrist which primarily effects the poor (fines).
Drug laws were already within this category before Ullbricht started the Silk Road. The was on drugs was explicitly started by Nixon as a war on the antiwar left and black people, and if you didn't fall into one of those categories, you were/are largely above drug laws, since enforcement generally targets those categories, while the social acceptability of popular drugs means that crimes of this nature are rarely reported.
Ullbricht's primary offense was breaking a law that was already broken ubiquitously. Society did not collapse before Ullbricht when these laws were broken, it did not collapse when Ullbricht broke them, and it does not collapse because of the myriad of darknet sites which immediately filled the void left by the Silk Road's closure. Ullbricht's arrest didn't end the blatant disregard for drug laws on the darknet, and yet somehow in the 11 years since his arrest, society still hasn't devolved into small tribes slaughtering each other.
In short, if people breaking drug laws was a real threat to society, then society would have devolved into tribes slaughtering each other already. We have had over 50 years of people ubiquitously breaking drug laws without societal collapse.
This structure is self-reinforcing and very resilient: few people here and there rejecting faith in rule of law, or authority of the courts, or money, don't make a difference - we write such people off as weirdos and carry on with our days, secure in knowledge our world will continue to work as it worked the day before. But if sufficient amount of people have their faith falter, that's where the trouble starts.
For example, if enough people stop trusting in the justice system to deliver something resembling justice most of the time, you'll see people ignoring courts and laws and taking justice into their own hands[0]. People start lynching and killing each other, others see them getting away with it, which quickly destroys their trust in the system, and now you're at the precipice. If shooting a (person accused of being) thief is fine, if shooting a billionaire is fine, then why uphold a contract? Might as well get your own at gunpoint, etc. At this point everything stops working - banks, healthcare, fire services, stores. Your country collapses. You probably die.
That is why threats to our shared belief system are so dangerous, and need to be dealt with swiftly and aggressively. It's not about elites in power wanting to stay in power (though it's no doubt part of it for them) - it's because should we all start thinking our social structures don't work, and that everyone else thinks this too, and start acting on this expectation, they'll all collapse in an instant.
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[0] - No, whatever it is that America has with its police is still far from that point.