The O'Reilly Update, May 19, 2026

President Donald Trump has called off a planned military strike on Iran after diplomatic pressure from Qatar, Saudi Arabia, and the UAE, while simultaneously warning that a full-scale assault remains on standby if diplomacy fails. The episode highlights the high-stakes political drama surrounding the Kentucky House primary, where Trump-endorsed candidate Ed Galrine, a former Navy SEAL, faces off against seven-term incumbent Thomas Massey in what’s become the most expensive House primary in history. Bill O’Reilly frames the race as a battle between loyalty to the party and independent thinking, arguing that consistent opposition to the party ultimately isolates a politician. In a bold policy move, Trump is expanding the Trump Rx website to include over 600 prescription drugs—seven times more than before—joining forces with Mark Cuban to push for lower drug prices across the political spectrum. O’Reilly also delivers a dramatic historical reflection on Marilyn Monroe’s final performance for JFK on May 19, 1962, linking her death three months later to enduring conspiracy theories about the Kennedy brothers, Hollywood, and the mob. The episode closes with a mix of political analysis, cultural commentary, and consumer promotions, underscoring O’Reilly’s signature blend of alarmism, patriotism, and pop culture nostalgia.