For two decades, when the tribulations of the famous and the notorious have aired on television, Mickey Sherman has been there to talk and talk: about O. J. Simpson, Martha Stewart, Michael Vick, Casey Anthony, Michael Jackson, just to name a few whose legal cases he analyzed for the camera. When Nancy Grace needed help explaining how a man accused of murder had walked free even after the victims’ bodies were found in his backyard, Mr. Sherman was there, making the CNN studio peal with laughter.

“You get a client with 8 to 12 bodies buried in his yard, and there’s an immediate rush to judgment that he may have done something wrong,” he deadpanned.

The public’s insatiable appetite for true-crime programming vaulted Mr. Sherman, the assured, accessible and witty defense lawyer from Greenwich, Conn., into the flashy television-personality world of photo shoots and celebrity hobnobbing.

But now Mr. Sherman is the one whom the talking heads are talking about.

Last week, a Connecticut judge ordered a retrial for Mr. Sherman’s most famous client, Michael C. Skakel, the nephew of Ethel Kennedy who was convicted in 2002 of killing a neighbor, Martha Moxley, when both were 15 in 1975. In a scathing, 136-page decision, the judge wrote that had Mr. Sherman not done such a poor job defending Mr. Skakel, the jury might have come to a different conclusion.