I had never been robbed before, not once at all. But after getting the DLC which again I'm pretty sure is irrelevant right? The thief came to take my money.
I started a new character for this and oddly enough, I was able to tell him I was part of the thieves guild even though I had not even heard of the guild yet in that play through.
He simply says, "oh yeah, I think I've seen you around the tavern!"
And runs off.
That seems kind of, unusual to me that I had the option to say something that my character wasn't even aware existed lol.