Dean. I think they'll both miss him terribly but I believe that Dean's connection with Bobby is pretty much the same if not more then his was with John so it would be like losing John all over again.
i think dean would b the most upset b/c bobbys death b/c he holds back everything til him and bobby get alone then he spills
sam his guts about how sam has changed plus bobby is the only one that actually tells him anything
Dean,because he spent more time with bobby in childhood,in the episode of bobby's death,in flash back bobby and dean(as a young kid) were playing together.so i think dean is more upset of bobby's death.