Claim: Dennis Hastert originally lost a bid for a political position.

John Dennis Hastert -LRB- -LSB- ˈhæstərt -RSB- born January 2 , 1942 -RRB- is an American former congressman who served as the 51st Speaker of the United States House of Representatives from 1999 to 2007 , representing from 1987 to 2007 . He is the longest-serving Republican Speaker of the House in history , and one of the highest-ranking politicians in U.S. history to have gone to prison .   Hastert grew up in rural Illinois . He graduated from Wheaton College with a degree in economics in 1964 and obtained an education degree from Northern Illinois University three years later . From 1965 to 1981 , Hastert was a high school teacher and coach . He lost a 1980 bid for the Illinois House of Representatives , but tried again and won a seat in 1981 . He was first elected to the United States House of Representatives in 1986 , and re-elected every subsequent election until he retired in 2007 . Hastert rose through the Republican ranks in the House , becoming chief deputy whip and eventually Speaker in 1999 . As Speaker of the House , Hastert supported the George W. Bush administration 's foreign and domestic policies . After Democrats took control of the House in 2007 following the 2006 election , Hastert chose not to seek the position of minority leader , resigned his House seat , and became a lobbyist at the firm of Dickstein Shapiro .   In May 2015 , Hastert was indicted on federal charges of structuring bank withdrawals to evade bank reporting requirements and making false statements to federal investigators . Federal prosecutors said that the money was to compensate for and conceal deliberately-unspecified misconduct by Hastert against an unnamed individual years earlier . Soon afterward , public accusations emerged that Hastert had sexually abused three male students -LRB- including the aforementioned unnamed individual -RRB- when he was a teacher more than three decades earlier .   In October 2015 , Hastert entered into a plea agreement with prosecutors . Under the agreement , Hastert pleaded guilty to the `` structuring '' charge -LRB- a felony -RRB- , and the charge of making false statements was dropped . In court submissions on sentencing considerations filed in April 2016 , federal prosecutors made allegations of sexual misconduct against Hastert , saying that he had molested at least four boys as young as 14 while he worked as a high school wrestling coach decades earlier . At the sentencing hearing later that month , Hastert admitted that he had sexually abused boys whom he coached . The judge in the case referred to Hastert as a `` serial child molester '' and imposed a sentence of fifteen months in prison , two years ' supervised release , and a $ 250,000 fine . He entered the Federal Medical Center prison in Rochester , Minnesota on June 22 , 2016 .