Roger Cressey

Roger W. Cressey
Born	9 8, 1965
Nationality	American
Occupation	Counterterrorism expert, cybersecurity consultant, defense analyst
Employer	Mountain Wave Ventures Liberty Group Ventures, LLC
Known for	Counterterrorism policy, cybersecurity advisory

Roger W. Cressey (born August 9, 1965) is an American counterterrorism and cybersecurity expert who served in senior national security positions under Presidents Bill Clinton and George W. Bush. A former member of the United States National Security Council staff, Cressey played a central role in the United States government's counterterrorism operations during the late 1990s and early 2000s, a period that encompassed the USS Cole bombing, the millennium plot, and the September 11 attacks. After leaving government service, Cressey became a prominent voice in national security commentary, serving as a counterterrorism analyst for NBC News and MSNBC, and built a career in the private sector as a consultant and executive in cybersecurity and defense. He has held positions at Booz Allen Hamilton, co-founded the Good Harbor consulting group, served as a partner at Liberty Group Ventures, LLC, and is currently associated with Mountain Wave Ventures. Cressey has also served as an adjunct professor of counterterrorism policy at Georgetown University and has testified before the United States Congress on national security matters.

Early Life

Roger W. Cressey was born on August 9, 1965. He grew up during the Cold War era and developed an early interest in international affairs and diplomacy. As a student in the mid-1980s, Cressey attended the University of Massachusetts Lowell, where he was involved in the Model United Nations program. A 2017 UMass Lowell Magazine feature recounted the university's Model U.N. tradition, noting its role in shaping students interested in international relations and diplomacy during the 1984–1987 period when Cressey was an undergraduate. This experience in simulated international negotiation and policy debate provided an early foundation for what would become a career focused on national security and counterterrorism policy.

After completing his undergraduate studies, Cressey pursued graduate education in Washington, D.C., positioning himself within the center of American policymaking. He earned a Master of Arts degree from George Washington University in 1991, further developing his expertise in international affairs and security studies.

Education

Cressey received his Bachelor of Arts degree from the University of Massachusetts Lowell in 1987. He subsequently earned a Master of Arts degree from George Washington University in 1991. His graduate education at George Washington University, located in the nation's capital, placed him in proximity to the federal government institutions where he would soon begin his career. Cressey has maintained ties with George Washington University; in 2025, he participated in the university's inaugural Cybersecurity Conference, hosted by the College of Professional Studies, where experts from the public and private sectors convened to discuss cybersecurity challenges.

Career

Government Service

Cressey's career in government spanned several critical years in the evolution of American counterterrorism policy. He served in senior positions on the National Security Council staff under both President Bill Clinton and President George W. Bush, working on counterterrorism and transnational threats during a period of escalating terrorist activity directed at the United States.

During his tenure on the NSC staff, Cressey was involved in the U.S. government's response to major terrorist incidents and threats. His service encompassed the period of the 1998 United States embassy bombings, the millennium plot of 1999–2000, the USS Cole bombing in October 2000, and the September 11 attacks in 2001. The 9/11 Commission Report, formally titled Final Report of the National Commission on Terrorist Attacks Upon the United States, documented the activities and structure of the NSC's counterterrorism apparatus during this period, providing context for the work carried out by officials such as Cressey.

A 2004 Washington Post report examined the role of national security policy experts and advisors during the period leading up to and following the September 11 attacks, providing further documentation of the interplay between counterterrorism officials and policymakers during Cressey's time in government.

Cressey has described himself as having served two U.S. presidents as a senior cybersecurity and counterterrorism advisor, a characterization consistent with his NSC positions under Clinton and Bush.

Media Career

After leaving government service, Cressey transitioned into a role as a media commentator and analyst. He became a counterterrorism analyst for NBC News and appeared regularly on NBC and MSNBC broadcasts, providing expert commentary on terrorism, national security, and related geopolitical developments.

In this capacity, Cressey provided on-air analysis of major national security events and policy debates. He appeared on NBC News programs to discuss topics including the evolving threat of al-Qaeda, the wars in Iraq and Afghanistan, and domestic security concerns. He also appeared multiple times on C-SPAN programming, discussing national security strategy and related policy matters. One notable C-SPAN appearance involved a discussion of national security strategy.

Cressey's media work was not without controversy. A report by ThinkProgress noted that during appearances on NBC discussing the political situation in Yemen, Cressey defended the Yemeni government while failing to disclose potential conflicts of interest related to his private-sector consulting work.

In 2004, Cressey authored an opinion piece for The New York Times in which he addressed the terrorist threat posed by Abu Musab al-Zarqawi, arguing that the threat should be assessed on its own terms without conflation with other policy objectives. He also contributed analysis to The Wall Street Journal on national security topics during this period.

Private Sector

Cressey's post-government career has also encompassed extensive work in the private sector, primarily in cybersecurity consulting and defense advisory services.

He co-founded the Good Harbor consulting group and served as its president. Good Harbor provided strategic advisory services in cybersecurity, counterterrorism, and homeland security to both government and private-sector clients.

Cressey subsequently served as a Senior Vice President at Booz Allen Hamilton, one of the largest management and technology consulting firms serving the U.S. government. In this role, he worked on cybersecurity and national security consulting engagements.

Following his tenure at Booz Allen Hamilton, Cressey became a partner at Liberty Group Ventures, LLC, a cybersecurity consulting firm.

As of 2025, Cressey is associated with Mountain Wave Ventures and has worked with Google Cloud, a competitor to Microsoft, in that capacity.

Cybersecurity Advocacy

In the 2020s, Cressey became an outspoken voice on federal government cybersecurity policy, particularly regarding the U.S. government's dependence on Microsoft products and the company's security track record. In a series of articles and public commentary in 2025, Cressey argued that Microsoft treats security as "an annoyance, not a necessity" and called on the federal government to demand higher security standards from its technology vendors or consider alternative providers.

In a May 2025 article published by SC Media, Cressey wrote that Microsoft needed to "get serious about secure software" and noted that the company had repeatedly promised the federal government it would improve its security posture, yet the situation remained largely unchanged. He argued that the federal government should be willing to seek new IT partners if Microsoft failed to deliver on its commitments.

In September 2025, Cressey authored a commentary for the Federal News Network titled "Microsoft promised a secure future. Where is it?" in which he continued to press the case for greater accountability from major technology providers serving the federal government. The article carried an editor's note disclosing that Cressey had worked with Google Cloud, a Microsoft competitor, through his position at Mountain Wave Ventures.

In an August 2025 interview with The Register, Cressey elaborated on his concerns, drawing on his experience as a White House cybersecurity and counterterrorism advisor to argue that the federal government's cybersecurity posture required fundamental reform. He expressed worry about the trajectory of government cybersecurity and the persistent challenges of securing federal information systems.

Public Speaking and Congressional Testimony

Cressey has been active as a public speaker on counterterrorism and cybersecurity topics. He has delivered keynote addresses at industry conferences, including the RSA Conference, one of the largest cybersecurity conferences in the world.

In October 2021, Cressey delivered a keynote presentation at the New York Alliance Against Computer Trickery (NYACT) annual anti-fraud conference, billed as the organization's largest event of the year. He was described at the event as an "NBC Counter-terrorism Analyst & Former Presidential Advisor."

Cressey has testified before the United States Senate on national security matters. A 2013 Senate hearing transcript documents his participation in congressional proceedings addressing intelligence and security policy. A 2012 Washington Post report on Senate committee proceedings related to intelligence leaks also documented aspects of the policy environment in which Cressey operated as a commentator and expert witness.

Academic Work

Cressey served as an adjunct professor of counterterrorism policy at Georgetown University, where he taught courses related to his areas of professional expertise. He has maintained academic connections throughout his career; his participation in the 2025 George Washington University Cybersecurity Conference reflected his continued engagement with academic institutions on security policy topics.

Writing on Federal Technology Transformation

In a piece published by FedScoop in early 2026, Cressey wrote about the prospect of "disruptive digital transformation" in the U.S. government, predicting improvements across public-sector technology. The article, authored by Cressey and drawing on his experience as a former Clinton and Bush cybersecurity expert, addressed the challenges and opportunities facing federal agencies as they adopted new technologies.

Recognition

Cressey has received recognition from multiple organizations for his contributions to the fields of counterterrorism and cybersecurity. In 2019, Security Magazine named him one of its "Most Influential People in Security," a designation that recognized his career spanning government service, private-sector consulting, and media commentary. The magazine's profile noted his roles at Liberty Group Ventures and his prior service as a Senior Vice President at Booz Allen Hamilton.

His career has placed him in a position of influence across multiple domains of national security policy. His government service under two presidents, combined with his media visibility as an NBC analyst and his private-sector roles at major consulting firms, has given him a platform from which to shape public discourse on counterterrorism and cybersecurity. His appearances on C-SPAN, NBC, and MSNBC, along with his written contributions to The New York Times, The Wall Street Journal, SC Media, Federal News Network, and FedScoop, have established him as a recurring commentator in national security debates.

His selection as a speaker at the RSA Conference further reflects his standing within the cybersecurity professional community.