Hopwood is the son of Robert Mark Hopwood and Becky Richards, who raised him in a Christian home. He grew up in David City, Nebraska, approximately an hour's drive northwest of Lincoln, Nebraska. Hopwood is the eldest of five siblings. Hopwood excelled on standardized tests. He was a high school basketball standout, earning himself a scholarship to Midland University in Fremont, Nebraska. After Hopwood realized he was a mediocre talent in basketball, he became disillusioned and did not go to classes. After leaving school, Hopwood joined the United States Navy. He was stationed in the Persian Gulf. While in the Navy, Hopwood guarded warships with shoulder-mounted Stinger missiles. He almost died from acute pancreatitis in a Bahrain hospital, which prompted his discharge from the Navy.
Bank robbery
Hopwood pled guilty on October 28, 1998, to robbing several banks in Nebraska. United States District Judge Richard G. Kopf sentenced Hopwood to 12 years, three months in prison followed by three years of supervised release and ordered $134,544 in restitution. Kopf was stunned by Hopwood's later transformation and said, "my gut told me that was a punk—all mouth, and very little else. My viscera was wrong." In Kopf's own opinion, "Hopwood proves that my sentencing instincts suck."
Jailhouse lawyer
Hopwood served his prison sentence at Federal Correctional Institution, Pekin. While at Pekin, he spent five weeks in solitary confinement, and criticized the practice once he got out. He prepared his first petition for certiorari for a fellow inmate on a prison typewriter in 2002. Since Hopwood was not a lawyer, the only name on the brief was that of the other prisoner, John Fellers. Once the Supreme Court agreed to hear the case, he worked with Seth Waxman, a former United States Solicitor General, in preparing the case. Waxman stated that the petition for writ of certiorari was probably one of the best he had ever seen. The court received 7,209 petitions that year from prisoners and others too poor to pay the filing fee, and it agreed to hear just eight of them. One was Fellers v. United States. The court, in a 9-0 decision, found that police had acted unconstitutionally in questioning Fellers, who had been convicted of a drug conspiracy. Fellers's sentence was ultimately reduced by four years. In 2005, the Supreme Court granted a second cert petition prepared by Hopwood, vacating a lower court decision and sending the case back for a fresh look. Hopwood has also helped inmates from Indiana, Michigan and Nebraska get sentence reductions of 3 to 10 years from lower courts. He also won honorable mention in the PEN American Center 2008 Prison Writing contest. Hopwood was released from the custody of the Bureau of Prisons on April 9, 2009. In 2010, he was working at Cockle Printing in Omaha, Nebraska, a leading printer of Supreme Court briefs.
Hopwood's memoir, Law Man: My Story of Robbing Banks, Winning Supreme Court Cases, and Finding Redemption, co-written with Dennis Burke, was published in August 2012. In the memoir, Hopwood details both his life as a jailhouse lawyer and his romance with his wife, Ann Marie Hopwood, who Hopwood wrote during eight years of his imprisonment. Law Man received critical acclaim from a number of book reviewers. Hopwood is a criminal justice advocate, and he has written about the need for federal sentencing and prison reform. Hopwood told an ACLU event that his home state of Nebraska should reform sentencing guidelines for prisoners, keep good time credits and not build a new prison.
Preface: Failing to Fix Sentencing Mistakes: How the System of Mass Incarceration May Have Hardened the Hearts of the Federal Judiciary, 43 Geo. L.J. Ann. Rev. Crim. Proc. iii
Slicing Through the Great Legal Gordian Knot: Ways to Assist Pro Se Litigants in Their Quest for Justice, 80 Fordham L. Rev. 1229
A Sunny Deposition: How the in Forma Pauperis Statute Provides an Avenue for Indigent Prisoners to Seek Depositions Without Accompanying Fees, 46 Harv. C.R.-C.L. L. Rev. 195
From a Prison Law Library to the New York Times, Informal Opinion, Champion, November 2010
In the media
Hopwood has been profiled by The New York Times, NPR, and other media. He was featured on a 60 Minutes segment in 2017 and repeated in 2019, where he was interviewed by Steve Kroft.