Played by David Weisenberg

The "Man In Suit" in episode 3x02 [New Kids On The Block] approaches Claire Simms, who is walking with Alan Shore on a Boston street, and gives her an unintelligible shriek/grunt of obvious disgust. Claire wonders, "Is it my hat?" and Alan responds: "More than likely". The problem? Claire is wearing a New York Yankees cap:


David Weisenberg
Weisenberg has made a career of playing small parts like this one. Among his many credits, he once played a tailor on an episode of David E. Kelley's Ally McBeal (2001). Prior to that, he appeared as a clerk in The Privateers (2000), which also featured frequent Boston Legal "court clerk", Zylan Brooks.

David Weisenberg at the Internet Movie Database.