Independent of his support for ISIS on Twitter, Ali Shukri Amin converted his friend Reza Niknejad to a radicalized form of Islam, put him in touch with an ISIS recruiter, convinced him to join ISIS in Syria, gave him instructions on how to transfer from Turkey to Syria, drove Reza Niknejad to the airport to fly to Turkey, and relayed messages between Reza Niknejad and his family informing them of what was happening. In all likelihood Reza Niknejad is going to die working for the worst terrorist organization in the world.
There's clearly a discussion to be had about whether educating ISIS-aspirants in the use of Bitcoin to evade laws against donating to ISIL counts as "training" under 18 USC 2339A. I agree that some of what's alleged in the plea deal comes pretty close to criminalizing being nice to ISIS.
But there's a pretty cut-and-dried case against Ali Shukri Amin even without the Twitter drama. This isn't a teenager sentenced for a few tweets. He has been convicted on a single count of "Material Support". He has stipulated the truth of the DOJ's allegations about Reza Niknejad. It seems clear that the facts support the single count he's charged with.
revised a bit for clarity, and to add the dig at Techdirt