Underwood served as the Guam Delegate to the US Congress in the 103rd through 107th Congresses from January 3, 1993 to January 3, 2003 during which he sponsored major legislation for Guam, played an active role in US Department of Defense authorization bills and was an advocate for political development for insular areas and the extension of educational and social opportunities for Asian Americans and Pacific Islanders. During his tenure in congress, he became a senior member of both the House Armed Services and Resources committees. He emphasized the importance of Guam and the Asian Pacific region in national strategic policy and worked to enhance the benefits of military personnel, especially those in guard and reserve units. He passed major legislation for Guam that resolved long standing land disputes with the federal government, brought recognition to Guam's World War II generation and their case for war claims and enhanced local autonomy. Additionally, he built a successful record of bringing in federal funds for military construction, assistance to the government of Guam due to in-migration from surrounding islands and for several education programs. Underwood ensured Guam's inclusion in major legislation such as the Telecommunications Act of 1996 that brought domestic telephone rates to Pacific territories, the State Children's Health Insurance Program and the bill that established the Department of Homeland Security. He brought recognition to Guam's unique people by lifting the ban on betel nut importation into the US Customs Zone, inclusion in the National World War II Memorial, the creation of Chamorro Standard Time and participation in national commemorative events. As a member of the Hispanic and Asian Pacific American Caucuses, he spoke out for the protection of immigrant rights, educational opportunities and sensitivity to language issues. As chairman of the Congressional Asian Pacific American Caucus in the 106th Congress, he led the effort to include Asian Pacific Americans in scholarship programs, was instrumental in the development of the White House Initiative on Asian Americans and Pacific Islanders, spoke out against racial profiling and for including Pacific Islanders as a demographic category in federal programs.
Underwood-Ada Gubernatorial Ticket (2002)
Underwood declared his candidacy for the 2002 gubernatorial election and was a candidate in the November 2002 General election. His running mate for Lt. Governor was Senator Thomas "Tom" Ada. Underwood was defeated by Felix Perez Camacho in the general election on November 3, 2002.
Underwood-Aguon Gubernatorial Ticket (2006)
Underwood ran again as a Democrat for Governor of Guam in 2006, with running mate Frank Aguon for Lieutenant Governor. The Underwood-Aguon team faced former governor Carl Gutierrez and Senator Benjamin Cruz. He defeated his main Democratic rival, for the Gutierrez-Cruz team in the primary election on September 2, 2006. But on November 7, 2006 he was defeated during the general elections when he re-elected to incumbent Republican Governor Felix Perez Camacho, along with his new running mate Lt. Governor-elect Dr. Michael Cruz for the percentage voters from 50%-48%.
UOG President
In 2008, Underwood was selected to begin a 5-year term as the tenth president of the University of Guam and has continued to hold this position as of 2016. In June 2018, Underwood retired as President of the University of Guam and was succeeded by Thomas W. Krise.
