It is this same extravagance that seems to have embroiled him in the federal bribery case involving Sheriff Carona, his wife and his mistress. Carona is accused in the indictment of corruptly using the office of the sheriff "to enrich himself." His wife, Deborah, and "longtime mistress," Debra Hoffman, are also linked to the "acceptance of cash payments, as well as gifts, trips, the use of yachts and private planes and other things of value," according to the indictment.
Amid the allegations of the acceptance of ringside tickets to championship boxing, the acceptance of bogus campaign contributions and numerous other charges, including the acceptance of Mont Blanc fountain pens worth $1,400, is Overt Act 59:
"On or about December 19, 2002, defendant Deborah Carona and co-conspirator George Jaramillo (assistant Sheriff George Jaramillo) accepted as gifts from H.A., a businessman who owned a data mining software company, yellow gold and diamond Ladies Cartier Watches worth approximately $15,000 each."
Asher is not named as a defendant in the case, and there is no allegation in the document that he attempted to influence any purchases or other decisions by the county.
But the gift is among the many that the Caronas and co-conspirator Hoffman failed to disclose. The pattern of alleged corruption led to them to be walked in handcuffs -- Sheriff Carona in the middle flanked by his wife and alleged mistress -- into federal custody.
For Giuliani, the disclosures regarding Asher again seem to demonstrate a propensity on the candidate's part for embracing controversial figures including Bernard Kerik, the disgraced former New York City police commissioner, a disgraced priest accused of pedophilia, a Pennsylvania fundraiser who was arrested, convicted and served time for bribery in connection with official duties, and convicted tax-dodger James Ortenzio, a key Rudy fundraiser and former head of the New York County Republican Party.
At Jari Research, an associate of Asher's said, "No one speaks for Mr. Asher" except Asher, and it did not appear likely he would return a call as he was immersed in a "celebration of life" for his sister. Asher hosted a similar celebration last week where Harry Connick Jr. serenaded the guests.
"This would seem to be another case of trying to find a story where there isn't one. Over the course of his career, Mayor Giuliani has worked with numerous well-respected and highly regarded individuals as a member of the Reagan Department of Justice, US Attorney, Mayor of New York and private practice," said Maria Comella, a spokesperson for Giuliani.
Sheriff Carona's attorney declined comment when reached by ABC News.