I will veer away a bit before I am through this comment. My first reaction to what you said as introduction to the linked article was to see an un funny joke, un funny to me that is,  about Manning's sexual issues. I assume it was said at least somewhat jokingly. I might laugh at the same joke told in a different context about a different person at a different time so I am not intending some political correctness slam against you, just sayin'.
 Next, though, I thought some more about something that has come to mind almost any time I have thought about what sentence Manning might get and now about what sentence he did get.

"...a way to keep himself occupied in the meantime..."

Manning got a severe sentence by any 'fair' standard I can imagine. The very best Manning can reasonably hope for is seven more years of confinement. Seven years. At best. Maybe. Possibly. IF he passes every new test thrown at him by his incarceration.The three years he has just spent are far beyond what I can imagine enduring. The next years are not going to be a pick-nick. They may possibly be no worse than for any other inmate, that's plenty bad enough, or they may be horrible.
  Manning has passed every hard test of ethics, morality, and courage that his military situation presented to him. Lots of soldiers have done worse even if their only failing was to stand by complicitly while others acted overtly. Now he faces seven years living among a criminal population of ex soldiers. My instincts tell me that that population has a higher percentage of actual criminals and criminals of a more anti-social nature than do most civilian prisons. A very high percentage of active military consider Manning to be a traitor. His guards are likely to be hostile but may not do anything overtly wrong. They might likely look the other way and complicitly say nothing when they see wrong things happen to someone they don't like anyway, someone the weight of their national culture and their local tribal gang tells them to despise for several reasons. Manning might look as much like fair game to them as did so many Iraqis to so many of the soldiers who operated in the same theatre as he did. Manning may experience a version of the Chinese curse. He may have an interesting life. He may stay occupied.

I voted for Bradley Manning today. I voted to say that he has done enough, he has done his duty. He has paid a price worthy of respected citizenship and freedom. It is time to let him go.
 My vote today, though almost certainly as pointless as most of my votes have been, was finally one that was not for the lesser of two evils.  And yes, I cannot help but think about what else I know, that I know it will get me on at least one list I don't want to be on. That is the Presidents email list, even if none other.

 https://petitions.whitehouse.gov/petition/restore-united-states%E2%80%99...