David Letterman Reveals Affair with Staffers After Being Blackmailed

Late night talk show host, David Letterman, known for his biting humor and calling out celebrities for their misdeeds, found himself in the midst of a scandal involving workplace infidelities.

In 2009, Letterman made a shocking confession on The Late Show with David Letterman, admitting to having s**ual relationships with women who worked for him.

However, it wasn't a voluntary admission; he came forward after being blackmailed.

During the October 1, 2009 episode of The Late Show, Letterman surprised the studio audience with an unusual monologue.

He openly confessed to engaging in inappropriate behavior with female staff members.

While he didn't provide explicit details or reveal the individuals involved, he explained that he felt compelled to make the confession publicly because someone was attempting to extort $2 million from him to keep his secrets hidden.

In his public statement, Letterman also apologized to his wife, Regina Lasko, whom he had been in a relationship with since 1986 before they got married in March 2009.

Despite the scandal, the couple remained together.

The blackmail threat came in the form of a package delivered to Letterman's address.

Inside were proofs of his affairs with staffers.

The accompanying letter stated that the accuser planned to publicly humiliate Letterman by writing a screenplay and a book about his exploits if he didn't pay up, according to The Guardian.

Letterman revealed that he cooperated with the authorities, playing along with the blackmailer's demands.

He even wrote a fake $2 million check to lure the extortionist out.

Eventually, the identity of the blackmailer was uncovered when he attempted to deposit the counterfeit check.

It turned out to be Robert “Joe” Halderman, a former CBS news producer who had worked on the show 48 Hours.

Halderman admitted to his involvement in the extortion plot.

He confessed to delivering the package containing the blackmail letter and his screenplay draft to Letterman's driver.

He also revealed that he had met with Letterman's lawyer on multiple occasions to discuss a payoff for his silence, as reported by CNN.

After his arrest, Halderman expressed remorse to Letterman and his family, including Lasko and their young son Harry.

He also apologized to one of the women mentioned in the blackmail documents, with whom he had a previous romantic relationship.

To avoid going to trial, Halderman accepted a plea deal that included a six-month jail sentence, probation, and 1,000 hours of community service.

This incident wasn't the first time Letterman faced an extortion attempt.

In 2005, Kelly Frank, a former handyman at Letterman's ranch, was arrested for allegedly plotting to kidnap Letterman's son.

While not convicted of the kidnapping plot, Frank was sentenced to 10 years in prison for overcharging Letterman for his services.

He was released on parole in 2018 after a brief escape from prison led to his recapture.

David Letterman's confession and the subsequent blackmail scandal shed light on the dark side of his personal life, proving that even those who expose others' misbehavior can have skeletons in their own closets.