What were the specific allegations of sexual harassment made against Bill O'Reilly?

1. The earliest, high‑profile suit: Andrea Mackris’ allegations

Andrea Mackris, a producer on The O’Reilly Factor, sued O’Reilly in 2004 alleging persistent unwelcome advances and explicit conduct — including his alleged telephone calls in which he made sexual comments and described masturbatory behavior (famously the “falafel/loofah” episode and references to using a vibrator), and that those communications constituted sexual harassment that created a hostile work environment; the dispute was litigated and settled confidentially after competing lawsuits between the parties ^{[5] [4] [6]}.

2. Multiple settlements and categories of complaints

Reporting by The New York Times and subsequent coverage identified that at least five women received roughly $13 million in payouts over about 14 years related to claims against O’Reilly, with the documented complaints including propositions, unwanted advances, lewd comments, and allegations of retaliation or threats of retaliation when women refused sexual advances; four of the five settled matters involved sexual‑harassment claims while another involved verbal abuse, according to coverage synthesizing the settlements and internal documents ^{[1] [2] [7]}.

3. A separate large payment and a Fox News analyst’s claim

A later report alleged a single $32 million payment by O’Reilly in conjunction with a complaint brought by a Fox News analyst, an amount that legal commentators called “highly unusual” for the circumstances; that payment and its timing became central to scrutiny over what Fox executives knew when renewing O’Reilly’s contract and fed questions about corporate tolerance of alleged misconduct ^{[8] [3] [9]}.

4. Specific behaviors described across accounts

Across the various accounts and documents compiled by news outlets, the specific behaviors alleged against O’Reilly included direct sexual propositions to colleagues and guests, graphic or lewd language in private calls and workplace interactions, requests or pressure for sexual relationships tied to career advancement, and in at least some accounts, threats or punitive treatment if women did not comply — claims that, in combination, portrayed an alleged pattern rather than isolated incidents ^{[7] [1] [6]}.

5. Denials, counterclaims, NDAs and legal strategy

O’Reilly consistently denied the allegations, and in several instances his lawyers characterized accusations as extortion attempts or falsehoods; he and Fox paid settlements without admitting liability and used NDAs in resolved matters, prompting criticism that confidentiality terms and preemptive litigation (O’Reilly sued at least one accuser) helped suppress public airing of allegations for years ^{[5] [4] [9]}.

6. Broader institutional context and differing interpretations

Coverage emphasized that these allegations emerged against a backdrop of other harassment scandals at Fox News, including Roger Ailes’ ouster, and that market and reputational pressures (advertiser withdrawals and public scrutiny) ultimately contributed to O’Reilly’s departure from the network even though he denied wrongdoing; commentators and legal experts debated whether settlements signaled culpability or were pragmatic attempts to avoid protracted litigation and exposure ^{[10] [3] [2]}.

7. Limits of public record and unresolved questions

The public record is constrained by confidential settlements, sealed agreements and competing narratives: many factual details remain under NDAs or known only via reporting and leaked documents, meaning certain specifics of individual encounters are documented in reporting but cannot be independently verified through court adjudication because most matters ended in settlement rather than trial ^{[4] [3] [8]}.