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Donald Trump’s Drug-Trafficking Pilot

Alex Constantine - April 6, 2025

Trump Vouched For Cocaine Trafficker

Candidate called felon "credit to the community"

FEBRUARY 16--Presidential contender Donald Trump, who has vowed to stanch the flow of narcotics and criminals entering the U.S. from Mexico, once wrote to a judge urging leniency for a friend who was convicted of distributing kilos of cocaine that had been smuggled into the country from Colombia, court records show.

In advance of Joseph Weichselbaum’s November 1987 sentencing by a U.S. District Court judge, Trump wrote that the drug trafficker was “conscientious, forthright, and diligent" and "a credit to the community.” ...

Weichselbaum, investigators learned, was friends with Joseph “Joey Ip” Ippolito, another Mafia-connected narcotics trafficker. Like Weichselbaum, Ippolito was a speedboat racer who also peddled cocaine.

In March 1981, after Ippolito’s co-driver, Joel Halpern, died in a crash on Lake Ponchartrain in New Orleans, Weichselbaum reportedly dispatched a plane to return Ippolito and his crew members to Florida. Three days after the accident, Ippolito traveled to New York to attend the funeral and burial of Halpern (who was a friend of the Weichselbaum brothers).

According to a police report obtained by TSG, Ippolito, pictured at right, was picked up at a Manhattan heliport by none other than wiseguy John Staluppi’s personal chauffeur, who was dispatched to shuttle Ippolito to the services and Halpern’s Westchester home. Like Weichselbaum, Staluppi had raced speedboats and would one day shuttle Trump’s high rollers to Atlantic City via his helicopter service.


EBRUARY 16--Presidential contender Donald Trump, who has vowed to stanch the flow of narcotics and criminals entering the U.S. from Mexico, once wrote to a judge urging leniency for a friend who was convicted of distributing kilos of cocaine that had been smuggled into the country from Colombia, court records show.

In advance of Joseph Weichselbaum’s November 1987 sentencing by a U.S. District Court judge, Trump wrote that the drug trafficker was “conscientious, forthright, and diligent" and "a credit to the community.”

At the time Trump wrote his character reference letter, Weichselbaum, then in his mid-40s, was already a twice-convicted felon. In addition to his 1986 plea to federal cocaine distribution and income tax charges, Weichselbaum’s rap sheet included prior convictions for grand theft auto and the embezzlement of more than $130,000 from a Brooklyn manufacturing firm where he worked for a decade.

Weichselbaum, who peddled drugs and palled around with wiseguys, seemed an odd choice for Trump to publicly embrace. Especially since the developer--who has never been known for empathetic gestures--owned casinos monitored by New Jersey regulators on the alert for licensees who maintained business or personal relationships with unsavory types.

In a court filing that referred to the laudatory correspondence sent by Trump and other Weichselbaum cronies, a federal prosecutor mocked the letters. Weichselbaum, the government lawyer wrote, used his friends to vouch for his redeeming qualities and claim that his criminal activities were a one-time aberration and “totally out of his character.” These friends, prosecutor Ann Marie Tracey sneered, apparently were “unaware of defendant’s previous convictions and his extensive drug dealings.” Weichselbaum, the prosecutor noted in another filing, “was a felon even before becoming a drug dealer.”

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DAILY NEWS 31 CASINO PANEL EYES TRUMP PAL'S HI-FLYIN' DEALS 40 August 17, 1990 8 Ex-con tied to Aycee firm By TOM ROBBINS Daily News Staff Writer -- New Jersey gaming officials are investigating a convicted cocaine trafficker's relationship with a company that flies high rollers to Atlantic City casinos. The state's Division of Gaming Enforcement is probing Joseph Weichselbaum, an admitted drug offender who built a small helicopter company into Atlantic City's biggest charter service and developed relationships with many of the resort's top figures. Those include Donald Trump, who had business dealings with Weichselbaum after Weichselbaum was indicted on federal drug charges in 1985. Investigators are examining Weichselbaum's alleged ties to American Business Aviation, which did $4 million in business with major casinos in 1989, its first year of operation. They also are looking at the circumstances under which Trump personally leased a luxury apartment to Weichselbaum two months after Weichselbaum told a top Trump aide he had been indicted, said a source close to the investigation.

Got 3 years Weichselbaum kept the apartment in Trump Plaza on E. 61st St. for a three-and-ahalf-year period during which he was banned by gaming officials from dealing with the casinos, pleaded guilty to drug and tax charges and was sentenced to a threeyear prison term. New Jersey casino licensing rules call for licensees to steer clear of questionable associates and generally be of "good character, integrity and honesty." Weichselbaum told The News he is "an unpaid consultant" to American Business Aviation, which he said he helped to form after his release from prison in 1989. Officials of the firm have told the gaming enforcement division, an arm of the state Casino Control Commission, that Weichselbaum has no role in the company.

John Parker, vice president of American Business Aviation, said in an interview, "Joe's not here in any form." He said Weichselbaum had been a consultant to a related firm, Aircraft Services Corp., but he had left that position last month. Swift rise in biz Weichselbaum's history with the casino industry dates to 1983, when he took over management of another charter firm, Damin Aviation, which later reorganized with different investors as American Business Aviation. Owned by Weichselbaum's brother and two other inves- relationship of an she could not recall whom she had told. Trump rented Weichselbaum a 32d-floor apartment in Trump Plaza two months after Weichselbaum alerted Bauer. "I told (Trump) I was looking for an apartment.

He said, 'I've got apartments,' Weichselbaum said. Weichselbaum, 49, said he paid for the $7,000-a-month, two-bedroom apartment in a "half-cash, half barter" arrangement. Under the deal, Weichselbaum's firm would provide helicopter service in exchange for a portion of the rent. In June 1986, the Division of Gaming Enforcement learned of his indictment and ordered Damin to sever all ties to Weichselbaum. "When I got removed from the company it reverted to straight cash," Weichselbaum said of the cash-barter arrangement.

"It turned out to be a sucko deal." Casino investigators later charged that Damin flouted the order by continuing to pay Weichselbaum's $100,000-a-year salary, medical benefits and a $3,000-a- month leased stretch limousine and driver. License saved ANOTHER PROBLEM seems to whom he once befriended in business tors, Damin rocketed to the top of the Atlantic City charter business, landing the Sands Casino, the Golden Nugget and Trump's two casinos as customers. George Henningsen, deputy director of the gaming division, said: "We are currently investigating (the helicopter firm) and the role of Joe Weichselbaum in that company. We're looking at it in terms of the casinos they did business with." Investigators would not comment on the specifics of the probe, but sources at the gaming division said the agency could file charges against casino operators who dealt with Weichselbaum and knew of his ouster from Damin at the order of gaming officials. Trump, whose casinos used both Damin and American Business Aviation, refused to be interviewed about his re- have cropped up for Donald Trump and court.

lationship with Weichselbaum. An attorney for the Trump Organization, Joseph Silver, said the relationship was "that of a vendor of helicopter service." 'Totally business' Weichselbaum told The News his relationship with Trump was "totally business," but acknowledged that the developer and casino owner had personally arranged the apartment lease and also wrote a letter to the federal judge who sentenced Weichselbaum. In October 1985, Weichselbaum was indicted on drug and tax conspiracy charges. A federal agent testified at his sentencing hearing that while living in Miami in the early 1980s, Weichselbaum served as a middleman between a pair of Colombian cocaine dealers and a Cincin- involving a convicted cocaine trafficker AP nati-based drug ring. The agent, Leo Rolfes, a member of a federal interagency drug task force, testified that Weichselbaum sold amounts ranging from one to three kilograms of cocaine on seven occasions between 1980 and 1982.

According to sworn testimony to gaming investigators, Weichselbaum tried to cushion the news of his indictment by quietly informing his casino contacts. Nancy Bauer, vice president for transportation at Trump's Castle, testified that Weichselbaum told her in October he had been indicted on "a minor drug problem.' A plaza apt. Bauer told The News she had relayed Weichselbaum's statement to others in the Trump organization, but said *I told (Trump) I was looking for an apartment. He said, "I've got apartments."' Joseph Weichselbaum A move to revoke Damin's license was rejected by the Casino Control Commission after two public hearings. In its defense, Damin submitted more than 20 affidavits of support, including three from top officials of Trump casinos.

In 1987, Weichselbaum pleaded guilty to one count of aiding and abetting drug sales and one count of tax fraud. Three dozen letters were submitted to Newark Federal Judge Harold Ackerman on the defendant's behalf from what Weichselbaum described to The News as "some pretty important people." Among them was Trump, who in a letter "told the judge I was a pretty nice guy," said Weichselbaum. Asked why Trump had written a letter to the judge, Silver said: "Wouldn't you if you had a five-year business relationship with someone and you were friendly with them?" Weichselbaum began his prison term in January 1988, and was released to a federal halfway house 18 months later. Shortly before his release, Trump brought eviction proceedings against Weichselbaum for failing to pay four months rent, Silver said. When he was paroled in January, Weichselbaum moved into even classier Trump lodgings: two adjoining apartments on the 49th floor of Trump Tower on Fifth Ave. that he said his girlfriend bought for $2.35 million.