Chapter 20 - David Letterman and Staff Affairs - A Scandal in Late-Night Television

            David Letterman, one of the most iconic figures in late-night television, built a career on his sharp wit, irreverent humor, and charismatic presence. However, his personal life became the center of a shocking controversy in 2009 when he publicly admitted to having affairs with female staff members of his show. This revelation came as a result of an extortion attempt by Robert "Joe" Halderman, a CBS producer, who threatened to expose the affairs unless he was paid a significant sum of money. Letterman's confession sent shockwaves through the entertainment industry and raised broader conversations about workplace ethics, power dynamics, and media accountability.

            David Letterman was a pioneer in American late-night television. He began his career as a stand-up comedian before transitioning to television, hosting ‘Late Night with David Letterman’ on NBC from 1982 to 1993. After losing the ‘Tonight Show’ slot to Jay Leno, he moved to CBS and hosted ‘The Late Show with David Letterman’ from 1993 until his retirement in 2015. His brand of humor, known for its sarcasm and absurdist elements, won him a devoted audience and influenced a generation of talk show hosts.

            In October 2009, Letterman stunned his audience when he opened his monologue with a startling confession. He revealed that he had received a package containing a letter demanding $2 million in exchange for keeping his extramarital affairs with staff members secret. Rather than succumbing to blackmail, Letterman chose to cooperate with authorities, leading to the arrest of Robert Halderman, a CBS ‘48 Hours’ producer.

            Halderman had allegedly discovered details about Letterman’s affairs through his then-girlfriend, Stephanie Birkitt, who was a former assistant to Letterman and a recurring figure on his show. Halderman had found evidence, including a diary, detailing her relationship with Letterman. Using this information, he tried to coerce Letterman into paying hush money. However, Letterman worked with the Manhattan District Attorney’s office, setting up a sting operation that led to Halderman’s arrest on charges of attempted grand larceny.

            Instead of allowing rumors and speculation to fester, Letterman took the unusual step of addressing the issue directly on his show. He acknowledged his wrongdoing, saying:

“I have had sex with women who work for me on this show. My response to that is: Yes, I have. Would it be embarrassing if it were made public? Perhaps it would. Especially for the women.”

            His candid admission was met with a mixture of shock, admiration, and criticism. Some viewers praised his honesty and willingness to confront the issue head-on, while others condemned him for engaging in inappropriate workplace relationships.

            Letterman’s admission sparked a national discussion about workplace relationships, particularly those involving power imbalances. Critics pointed out that as the head of ‘The Late Show’, Letterman held considerable influence over his employees, making it difficult to determine whether the relationships were truly consensual or influenced by power dynamics. The incident also raised questions about how female employees in the entertainment industry navigate workplace relationships in male-dominated environments.

            Reactions to the scandal were mixed. Some of Letterman’s fans and industry peers commended him for coming clean, while others felt he had abused his position. Feminist groups and workplace ethics advocates highlighted the problematic nature of his actions, arguing that such relationships could create an unhealthy work environment. However, due to his swift admission and handling of the situation, Letterman’s reputation did not suffer long-term damage, and he continued hosting ‘The Late Show’ without facing significant professional consequences.

            Despite the controversy, Letterman remained a dominant force in late-night television. Unlike other public figures who faced career-ending backlash for similar transgressions, Letterman managed to maintain his position largely because of how he handled the situation. He took responsibility, did not attempt to downplay the seriousness of the allegations, and refrained from victim-blaming. Additionally, public sentiment towards him was generally forgiving, as his scandal was seen as a personal failing rather than a pattern of egregious behavior. 

            Robert Halderman was charged with attempted grand larceny and later accepted a plea deal. In March 2010, he pleaded guilty and was sentenced to six months in jail, five years of probation, and 1,000 hours of community service. His career in journalism effectively ended as a result of his actions.

            Letterman’s scandal occurred in a pre-#MeToo era, but it highlighted issues that would become central to workplace ethics discussions in the years to come. Had the scandal emerged in the wake of the #MeToo movement, it might have been met with more severe repercussions. The entertainment industry has since become more aware of the implications of power dynamics in workplace relationships, with companies implementing stricter policies against such conduct.

            David Letterman’s admission of affairs with his female staff members was a moment of reckoning for late-night television and workplace ethics. While he faced public scrutiny, his transparency and willingness to accept responsibility allowed him to weather the storm relatively unscathed. The incident also shed light on broader issues regarding power and consent in professional settings, paving the way for more discussions about ethical workplace relationships. Letterman’s legacy remains significant, but his scandal serves as a reminder of the personal and professional consequences of such actions.