In 1999, then-New York City Corrections Commissioner Bernard Kerik offered a birthday toast to his friend Larry Ray.
"He's someone with integrity, with honor, with courage. And most importantly, a friend for all friends," says Kerik on a 5-year-old videotape.
But that friendship is long over.
"I believe him to be dishonest," says Ray.
In an exclusive interview with NBC News, Ray says the White House should have talked to him before nominating Kerik as secretary of homeland security.
In a 1999 e-mail, Ray says Kerik offers to provide inside details about a city investigation to a firm suspected of ties to organized crime — Interstate Industrial. Video from Ray's birthday party in 1999 shows Kerik with company President Frank DiTommaso.
"They really wanted help with their problem getting licenses," says Ray. "[Kerik] tried and I believe he had some help with it."
DiTommaso and the firm deny any ties to the mob. Kerik denies providing inside information.
Ray also claims Kerik repeatedly asked him for money — for his wedding, expensive decorations and even the down payment for an apartment.
"He would say, 'I'm desperate. I need this help,’" says Ray.
How many thousands of dollars did Ray give Kerik over the years?
"I would say easily, easily beyond $50,000," says Ray.
And Ray says Kerik never paid any of it back.
More e-mails, which Ray says are from Kerik, contain the lines "I'm broke" and "can we spare $2,500 to get me by?"
But Ray has a checkered history himself. Former federal officials say Ray served as a valuable undercover operative for years. But last year, he pleaded guilty to conspiracy to commit fraud in a stock scheme involving mob associates.
So why should anyone believe him?
"Anything I say, I have documents to support," says Ray.
Kerik's lawyer says any gifts from Ray were small and that Ray is angry because Kerik refused to help when Ray was in legal trouble.
"I don't think it changes the fact that Bernie Kerik, remains, and still is, a hero," says Kerik's attorney Joseph Tacopina. "Larry Ray is someone whose credibility seriously has to be called into question."
Ray insists he is speaking out now out of patriotic duty.
Kerik now faces a city investigation for allegedly failing to report the gifts. Ray says there's no hint former Mayor Rudolph Giuliani, who pushed Kerik's nomination, knew about any of this.