In his first run for political office, he upset 18-term Democratic incumbent Jim Oberstar by a margin of 4,400 votes to become the first Republican since 1947 to represent the district.

[14][7] He graduated from the United States Naval Academy in 1981 with a bachelor of science degree and a Master's of Education from the University of West Florida in 1989.

He was out of work for two years in the early 1990s due to layoffs, during which time he became a simulator instructor for a subsidiary of Northwest Airlines teaching foreign pilots.

[7] Cravaack moved to New Hampshire after Congress to be with his sons, where he spent the last eight years before retirement as a teacher at Bishop Guertin High School, teaching U.S. History, Economics, and U.S.

[citation needed] He is now retired and shuttles between the Winnipesaukee area in New Hampshire and the cradle of Naval Aviation, Pensacola, Florida.

[citation needed] Cravaack was inspired to run for Congress by a suggestion from a talk radio show host that voters demand town hall meetings with their congressmen during the health care bill Tea Party movement protests of August 2009.

[7] He toured the district in a motor home dubbed "The War Wagon," and gave volunteers ranks such as commander, captain, and precinct lieutenant.

[11] In the November 2 election, Cravaack scored one of the biggest upsets in Minnesota political history,[20] unseating Oberstar by a vote of 133,490 (48%) to 129,091 (47%).

[24] He also received attention for implying during a House Homeland Security Committee hearing that Los Angeles County Sheriff Lee Baca was furthering the goals of a terrorist organization.

[25] In March 2012, Cravaack introduced a bill in Congress that would have allowed mining and logging in the Boundary Waters Canoe Area Wilderness and Superior National Forest through a land exchange that would rely on the state environmental review process and bypass federal environmental reviews, with proceeds going to the school districts.

[26][27] He also sponsored a bill, which became law, that required the TSA to treat military personnel with respect while traveling on orders or in uniform.