To be fair, I think that 2nd picture was from an episode of Top Gear filmed in Cuba where Clarkson and crew find Che Guevaras old Chevy, attempts to get it running and drive it, it was actually pretty funny.
http://www.topgear.com/uk/photos/Cuba-Libre-2013-12-12?imageNo=6
I couldnt find that clip but I found this one:
https://www.youtube.com/watch?v=qAW2OnuxDSQ
A lot of people dont get Clarksons humor which is very acerbic and highly satirical. And I have no doubt hes the kind of guy who would wear a Che Guevara tee shirt just to get you to comment on it and allow him the opportunity to tell you what a murderous a$$ hole Che actually was.
↑ That's not a '57 Chevy...
Although, when I found out he punched Piers Morgan, I decided to rethink my opinion, but it's hard to get over an idiotic Che shirt.