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They’re hard to keep straight, the various and sundry friends and business associates of Rudy Giuliani with legal problems. But here’s one worth keeping an eye on: Hank Asher. ABC reports that Asher, a former drug-runner, as well as a business partner and “close friend” of Giuliani’s, makes an appearance in the recent indictment of Orange County Sheriff Michael Carona on bribery charges.

Carona himself was once a rising star in the GOP, often mentioned as a potential candidate for lieutenant governor of California. Dubbed “America’s Sheriff” by Larry King for how he handled the 2002 hunt for 5-year-old Samantha Runnion’s kidnapper, he naturally endorsed America’s Mayor Rudy Giuliani for president. According to news accounts, he’s met Giuliani at least twice. He’s also chums with Bernie Kerik.

The indictment alleges that Carona and five associates, including his wife (Deborah) and mistress (named Debra), accepted bribes and generally did what they could to get rich off Carona’s position ($700,000 in bribes and kickbacks). Among the dozens of illicit gifts enumerated in the indictment is this one:

On or about December 19, 2002, defendant Deborah Carona and co-conspirator Jaramillo’s wife [that’s Carona’s 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.

“H.A.”, according to ABC, is Hank Asher, who did indeed own a data mining software company called Seisint at the time (more about that later). Asher himself is worth “north of $700 million,” based mostly on his success selling his data mining product, which is called Matrix (he’s since sold it to LexisNexis). And yes, he did smuggle cocaine from Colombia to Florida aboard his private jet for eight months in 1980 and 1981. But he says he paid his dues by cooperating with federal agents to stop other runners.

But it sounds like Asher still likes to live large. During that same dinner meeting with the two wives at Carmine’s here in New York, he apparently got a bit rambunctious:

When Hank Asher reached into the bag and pulled out the two $15,000 gold Cartier watches, the holiday crowd at Carmine’s restaurant on 44th Street in Manhattan noticed, patrons recalled….

During the Carmine’s dinner, when Asher’s voice began to boom across the room, patrons recall him handing his black American Express card to the restaurant to pay for any inconvenience his boisterous party caused the other guests. He told the staff to buy everyone’s dinners and drinks and then peeled off a few $100 bills to tip strolling carolers in the restaurant.

As ABC notes, Asher isn’t named as a co-conspirator in the case, and “there is no allegation in the document that he attempted to influence any purchases or other decisions by the county.” Maybe it was just a nice Christmas gift. But the timing is enough to raise eyebrows. Because that’s when Asher was making a big push for law enforcement agencies to buy his product. Carona, famous as he was for tracking down child predators, would have been an asset to Asher, who was hawking a product designed to help authorities identify suspects by searching billions of public records. Carona and Asher would later serve together on the Board of Directors for the National Center for Missing & Exploited Children.

Certainly Asher had a broad strategy for selling his system. To help him sell to the federal government, his secret weapon was Rudy Giuliani, whom he’d hired for a staggering sum of money — under a contract that the two of them kept secret for years. More about that in a bit.

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