The big difference between the Bulger 'gag' and your OP joke (aside from relevance) is the fact that the O'Pea material is actually funny. Olympian was one of the most tyrannical moderators Imgflip has ever had - and all that power did not bode well with his fragility especially when it came to banter.
My problem (if you can even call it that) with the Whitey Bulger jokes was how quickly it overstayed its welcome. Those jokes never evolved or adapted and without an essay of context to explain it, nobody at a glance would even understand what it meant and if your humour is so esoteric it needs to be explained then it just wasn't funny.
The OP jokes were simple, relevant, adaptable and most importantly were *funny* (makes a BIG difference methinks).
The left are incapable of being funny and this just further proves that fact. They aren't even ironically funny; its actually tragic.