History is not short of men who reached high office while living lives that merited opprobrium. Dante populated about half of his Inferno with these sorts of figures. The novelty of the last half-century is that their misconduct is becoming more frequently revealed, and sometimes punished, in this life, before the demons of the underworld begin to have at them in the afterlife. Dennis Hastert belongs to that older company which Dante wrote about so vividly 700 years ago, in ways that — as Hastert reminded us — are still rather relevant today.
John Dennis Hastert was born in Aurora on Jan. 2, 1942, and grew up in the farm towns west of Chicago, working in the family feed business and wrestling in high school. He took a degree from Wheaton College in 1964 and a master’s in education from Northern Illinois University in 1967, then settled in at Yorkville High School, where he taught and coached until 1981. The Foxes won 11 straight conference titles and, in 1976, the Illinois state championship, the year he was named Illinois coach of the year. He served in the Illinois House, then won a seat in Congress in 1986, representing the 14th District.
House Speaker Dennis Hastert (R-IL) sits for a portrait in his Capitol Hill office on June 15, 2007. (AP Photo / Susan Walsh, File)
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House Speaker Rep. Dennis Hastert (R-IL) sits for a portrait in his Capitol Hill office on June 15, 2007. (AP Photo / Susan Walsh, File)
Hastert began climbing the rungs of the Washington power ladder when he was offered the opportunity to become chief deputy whip under Tom DeLay. When Newt Gingrich resigned from the speakership after the 1998 elections and Bob Livingston, the heir apparent, withdrew amid an admitted affair, the conference turned to the deputy nobody had imagined in the chair. (Those who saw the excellent Netflix miniseries Death by Lightning may see in Hastert a kind of Speaker of the House version of President James Garfield — both were unassuming-seeming Midwesterners who rose to the pinnacle of political power in surprisingly unexpected ways. Garfield, though, by most accounts had a sublime sense of decency in his private life that Hastert unfortunately lacked in his.) On Jan. 6, 1999, Hastert became the 51st speaker, second in the line of presidential succession, and the accidental occupant of a job he would hold longer than any Republican before him.
Hastert was an effective speaker insofar as he was instrumental in helping President George W. Bush pass much of his agenda, from tax cuts and the No Child Left Behind Act to the Medicare prescription-drug benefit and the post-Sept. 11 security bills. After Democrats took the House in 2006, he stepped aside. In August 2007, he announced that he would not run again. “Who would have guessed,” he said, “that a wrestling coach from Kendall County in Illinois would be the longest-serving Republican speaker of the House of Representatives in all our nation’s history?” He resigned that November and became a lobbyist.
Speaker of the House Rep. Dennis Hastert (R-IL), left, introduces President George W. Bush at the National Republican Congressional Committee dinner on March 16, 2006 in Washington. (AP Photo / Evan Vucci)
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House Speaker Rep. Dennis Hastert (R-IL), left, introduces President George W. Bush at the National Republican Congressional Committee dinner on March 16, 2006 in Washington, D.C.. (AP Photo / Evan Vucci)
In the meantime, his past misdeeds were beginning to catch up with him. In 2015, federal prosecutors charged him with structuring bank withdrawals to evade reporting rules and with lying to the FBI about the cash. He had agreed in 2010 to pay $3.5 million to a man identified only as Individual A, a former wrestler, and had already handed over about $1.7 million. Of that, $952,000 was withdrawn in mostly $9,000 increments, just under the $10,000 reporting threshold, in 106 transactions. The money was hush money. Prosecutors said he had sexually abused at least four boys, some as young as 14, between 1965 and 1981 — in a motel room on a wrestling-camp trip, and in the locker room. The statute of limitations had run on the abuse. The banking crime had not.
JON KYL, 1942-2026
He pled guilty to the structuring count. At his sentencing in 2016, Judge Thomas M. Durkin rejected the prosecutors’ recommendation of no more than six months, and a defense request for probation, and sent him to prison for 15 months, with a $250,000 fine, supervised release, and sex-offender treatment. “Nothing is more stunning,” Durkin said, “than to have the words ‘serial child molester’ and ‘speaker of the House’ in the same sentence.” Hastert sat in a wheelchair for much of the hearing, then rose with a walker and told the court he was deeply ashamed. “They looked up to me,” he said of the boys, “and I took advantage of them.” He served about 13 months in prison and was transferred to a halfway house in July 2017. Federal custody ended that August.
Wheaton had already, in May 2015, taken his name off the J. Dennis Hastert Center for Economics, Government and Public Policy. He lived out of view afterward and died on Oct. 3, 2026, at his home in Plano, in Kendall County, while under hospice care. He was 84.
Daniel Ross Goodman (@DanRossGoodman) is a Washington Examiner contributing writer and teaches theology and religious studies at St. John’s University. His next book, Dante’s Guide to Life: How The Divine Comedy Can Change Our Fortunes, Our World, and Ourselves, will be published this fall by Angelico Press.
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