Roy, did you steal that hat from Pam? Or do you both shop in the same stores?
Oh, and some of Toby's misfortune is his own fault. I mean all the cr*p he takes from Michael. . .

Who else in the office would take that amount of humiliation? Michael isn't even his boss.
Also, he's solely responsible for not asking Pam out when he found out she was dating again.
Jeeze Toby, take a page from Angela's book of "wisdom" and grow a pair.
On the other hand, Toby is definitely familiar with the passive-aggressive approach. By "missing" the Booze Cruise, ducking out of the warehouse activities during Boys and Girls, classic Toby. Taking the opportunity to tell Michael that he knew about the branch closing just before Michael did was a golden opportunity to put Michael in his place, and of course taking his money on Casino Night, (lady luck helped him there).
I hope Toby's chasing that feeling. . .