Roger Cressey

Roger W. Cressey
Born	9 8, 1965
Nationality	American
Occupation	Counterterrorism expert, cybersecurity consultant, television analyst
Employer	Mountain Wave Ventures Liberty Group Ventures, LLC
Known for	Counterterrorism policy, cybersecurity advocacy, senior National Security Council staff under Presidents Clinton and Bush

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 was intimately involved in the U.S. government's counterterrorism apparatus during one of the most consequential periods in modern American history, including the period surrounding the September 11 attacks. After departing government service, he built a career as a prominent media analyst, serving as NBC News's counterterrorism analyst, and as a consultant and executive in the private sector cybersecurity space. Cressey founded and served as president of the Good Harbor consulting group, held a senior vice president position at Booz Allen Hamilton, and became a partner with Liberty Group Ventures, LLC. He has also served as an adjunct professor of counterterrorism policy at Georgetown University and has been an active commentator on federal cybersecurity policy, particularly regarding the U.S. government's reliance on major technology vendors. In recent years, Cressey has worked with Mountain Wave Ventures and continued to write and speak on topics related to digital transformation in the federal government.

Early Life

Roger W. Cressey was born on August 9, 1965. Details about his early childhood and family background are not widely documented in public sources. What is known is that Cressey's formative academic experiences took place at the University of Massachusetts Lowell, where he was a student in the mid-1980s. A 2017 profile in UMass Lowell Magazine recounted the university's Model United Nations program during the 1984–1985 period, a time when Cressey was an undergraduate student on campus. The Model U.N. experience was one of many formative academic exercises that helped shape the interests and analytical skills of students at UMass Lowell during that era, and Cressey would go on to pursue a career centered on international affairs and national security.

Cressey graduated from the University of Massachusetts Lowell with a Bachelor of Arts degree in 1987. His undergraduate education provided a foundation for what would become a distinguished career in government service and national security policy. After completing his undergraduate studies, Cressey pursued graduate education in the Washington, D.C., area, positioning himself near the center of American policymaking.

Education

Cressey earned 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 studies at George Washington University, located in the heart of Washington, D.C., placed him in proximity to the national security establishment and policy institutions that would define his professional career. George Washington University has a long history of producing graduates who serve in the federal government, intelligence community, and defense sector, and Cressey became one of its notable alumni in the counterterrorism and cybersecurity fields.

Career

Government Service

Cressey's career in government spanned the administrations of Presidents Bill Clinton and George W. Bush, during which he held senior positions related to national security and counterterrorism. He served as a member of the United States National Security Council (NSC) staff, where he was involved in the development and execution of counterterrorism policy at the highest levels of the U.S. government.

Cressey's government service coincided with a period of escalating terrorist threats against the United States, culminating in the September 11 attacks of 2001. The 9/11 Commission Report, officially titled The National Commission on Terrorist Attacks Upon the United States, documented the activities of senior counterterrorism officials during this period, providing historical context for the work carried out by NSC staff members like Cressey.

During his time in government, Cressey developed expertise in the intersection of national security policy, intelligence operations, and the emerging field of cybersecurity. His roles provided him with direct experience in crisis management and interagency coordination on matters of terrorism and homeland security. He participated in discussions and briefings at the C-SPAN–documented level, appearing in proceedings related to national security strategy. Cressey's government career also included engagement with congressional oversight processes; records from the United States Senate indicate his involvement in discussions related to national security and intelligence matters.

In a 2004 opinion piece published in The New York Times, Cressey wrote about the terrorist threat posed by Abu Musab al-Zarqawi, drawing on his experience in government to argue that the threat from the militant leader was significant in its own right and did not require exaggeration. The piece demonstrated Cressey's willingness to engage publicly with policy debates and established him as a credible voice on counterterrorism issues in the national media.

A profile in The Washington Post examined the role of national security experts and policy advisors in public discourse, including figures like Cressey who transitioned from government service to media and consulting roles.

Media Career

After leaving government service, Cressey became a prominent presence in the national media as a counterterrorism and national security analyst. He served as NBC News's counterterrorism analyst, appearing regularly on the network's programs to provide expert commentary on terrorism-related events and national security developments.

His role at NBC News gave him a platform to translate complex national security issues for a broad public audience. Cressey's commentary spanned topics including terrorist threats, U.S. military operations, intelligence policy, and cybersecurity. He was frequently called upon to provide analysis during breaking news events related to terrorism and national security.

Cressey also appeared on C-SPAN programming, contributing to policy discussions and public affairs programs.

His media work drew both praise and scrutiny. A 2011 report by ThinkProgress examined potential conflicts of interest among television news analysts with ties to defense contractors and consulting firms, noting that Cressey's dual roles as a media analyst and private-sector consultant raised questions about disclosure. Such scrutiny reflected broader concerns in media criticism about the revolving door between government service, private-sector consulting, and television commentary on national security issues.

Private Sector and Consulting

Cressey transitioned into the private sector, leveraging his government experience to build a career in cybersecurity and national security consulting. He founded and served as president of the Good Harbor consulting group, a firm specializing in cybersecurity and risk management.

He subsequently held the position of Senior Vice President at Booz Allen Hamilton, one of the largest management and technology consulting firms serving the U.S. government and defense sector. In this role, Cressey worked on cybersecurity strategy and risk assessment for government and private-sector clients. Booz Allen Hamilton's work in the intelligence and defense sectors aligned with Cressey's expertise in counterterrorism and national security policy.

Cressey became a partner with Liberty Group Ventures, LLC, a cybersecurity consulting firm. He has also been associated with Mountain Wave Ventures, through which he has worked with Google Cloud.

Cressey has been a frequent speaker at major cybersecurity and technology conferences, including the RSA Conference, one of the largest information security gatherings in the world. He has also spoken at anti-fraud and financial crime conferences, including the New York Anti-Crime Trust (NYACT) annual conference in 2021, where he delivered a keynote presentation drawing on his experience as a presidential advisor and counterterrorism analyst.

Academic Work

Cressey served as an adjunct professor of counterterrorism policy at Georgetown University, where he taught courses related to national security and counterterrorism. His academic role allowed him to share his firsthand government experience with graduate students pursuing careers in national security and intelligence. Georgetown University's School of Foreign Service is one of the leading programs in the country for international affairs and security studies, and Cressey's appointment reflected his standing in the counterterrorism community.

In 2025, Cressey participated in an inaugural cybersecurity conference hosted by George Washington University, his graduate alma mater. The conference brought together experts from the public and private sectors to discuss cybersecurity challenges facing the nation.

Cybersecurity Policy Advocacy

In the 2020s, Cressey became an outspoken commentator on federal cybersecurity policy, particularly regarding the U.S. government's dependence on Microsoft products and services. In a series of articles and public appearances, he argued that Microsoft had not adequately prioritized security in its products and that the federal government needed to hold the company accountable or consider alternative technology providers.

In a May 2025 commentary published in SC Media, Cressey wrote that Microsoft needed to "get serious about secure software" and argued that the federal government had repeatedly accepted Microsoft's promises to improve its security posture without seeing meaningful results.

In August 2025, The Register profiled Cressey's views on Microsoft's approach to security, quoting him as characterizing Microsoft as treating security as "an annoyance, not a necessity." The article noted Cressey's background as a senior cybersecurity and counterterrorism advisor to two U.S. presidents, lending weight to his critique.

In September 2025, Cressey published a commentary in the Federal News Network under the headline "Microsoft promised a secure future. Where is it?" The piece continued his criticism of Microsoft's security practices and called for greater accountability. An editor's note accompanying the article disclosed that Cressey had worked with Google Cloud, a Microsoft competitor, through his position at Mountain Wave Ventures.

Cressey also wrote about broader digital transformation in the federal government. In a piece published by FedScoop in early 2026, he predicted "disruptive digital transformation" across public-sector technology and outlined areas where he expected improvements in government technology adoption.

Personal Life

Cressey has maintained a relatively private personal life. Public records confirm his birth date of August 9, 1965. Beyond his professional activities, Cressey has not made extensive personal details publicly available. His public profile is primarily defined by his professional contributions to counterterrorism policy, cybersecurity, and national security commentary.

Recognition

Cressey has received recognition 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 distinction that recognized his career spanning government service, private-sector consulting, and media commentary. The recognition noted his roles at Liberty Group Ventures and his prior service as a Senior Vice President at Booz Allen Hamilton, as well as his extensive government experience.

His selection as a keynote speaker at numerous national and international conferences, including the RSA Conference and the NYACT anti-fraud conference, reflects his standing as a recognized authority on counterterrorism and cybersecurity issues. Cressey's opinion pieces have been published in major national outlets, including The New York Times, The Wall Street Journal, the Federal News Network, SC Media, and FedScoop, further establishing his reputation as a credible and influential voice in national security discourse.

His role as NBC News's counterterrorism analyst provided him with one of the largest media platforms available to national security experts, and his commentary reached millions of viewers during periods of heightened public concern about terrorism and security threats.

Legacy

Roger Cressey's career reflects the evolution of American counterterrorism and cybersecurity policy from the late 1990s through the 2020s. His service on the National Security Council staff during the Clinton and Bush administrations placed him at the center of U.S. counterterrorism efforts during a period that included the escalation of the al-Qaeda threat and the aftermath of the September 11 attacks. His subsequent career in media, consulting, and academia demonstrated a model—common among senior national security officials—of translating government experience into influence across multiple sectors.

Cressey's advocacy on federal cybersecurity policy, particularly his sustained criticism of the government's reliance on Microsoft and his calls for higher security standards from major technology vendors, has contributed to an ongoing national conversation about the security of government information technology infrastructure. His willingness to publicly challenge the status quo in government technology procurement, while disclosing his own private-sector affiliations, has positioned him as a notable participant in debates over federal cybersecurity governance.

As an educator at Georgetown University and a participant in academic conferences at George Washington University and elsewhere, Cressey has contributed to the development of the next generation of national security professionals. His career trajectory—from government service to media commentary to private-sector consulting and academic teaching—illustrates the interconnected nature of the national security community in the United States and the multiple pathways through which former government officials continue to shape policy and public understanding.