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His relationship with President Donald Trump was pivotal. Initially serving as the Deputy Assistant to the President and Deputy National Security Advisor, O’Brien was a trusted voice in the administration. His calm, methodical approach stood in contrast to the often-chaotic environment of the West Wing. He was a key architect of the administration’s “Maximum Pressure” campaign against Iran, a strategy that aimed to cripple the Iranian economy through relentless sanctions. This aggressive posture defined a significant portion of U.S. foreign policy in the Middle East during Trump’s first term. His loyalty and competence did not go unnoticed, and in 2019, following the abrupt dismissal of John Bolton, President Trump tapped O’Brien to serve as his National Security Advisor. This was a role he occupied for over a year, guiding the administration through a tumultuous period that included the assassination of Iranian General Qasem Soleimani and the subsequent brinkmanship with Tehran. His ability to manage the immediate crisis and communicate the administration’s stance to the world was widely noted.