Theoretically, which is the riskier pick?

[317]

i kind of liken Upshaw to Jamarcus Russel. all the physical tools in the world (not as much as Russel) but has a substance abuse problem. some people overcome those issues and others dont, there are a ton of variables. still for a second round pick you can cut the player loose at any time at no additional cost, so if you think you can put a support system in place then maybe you can have a Josh Hamilton turnaround situation.

[Neurotic Guy]

I know almost nothing about Upshaw, and the little I know makes me think that the C's should/will steer clear of him. 

That said, there have been many guys with personality, MH, or substance issues who had productive careers. A few examples: Vin Baker, Chris Mullen, Ron Artest, Dennis Rodman and Delonte West (well, a reasonably productive career for DW).  Baker was eventually done in by his problems, but not before many 20/10 seasons.  Mullen got completely past his issues.  Artest and Rodman had great careers.  Of course, lots of examples of guys who never made it.   

I do believe that the support system in place makes the difference for a lot of players.  Nowadays, teams should be able to provide better supports.  We'll see what happens with Royce White.