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The recent, unrelated arrests of Joseph Duggar and Kendra Caldwell have once again thrust the Duggar family into the public eye, reviving interest in a family that had largely faded from the spotlight. Once hailed as reality TV stars during their decade-long run on TLC, the Duggars were portrayed as paragons of wholesomeness. However, beneath this facade lies a family history marked by controversy and a surprising number of legal troubles.
Before Josh Duggar disgraced the family, Jimmy Lee Duggar spent time in jail
Before the world came to know the Duggars, Jim Bob Duggar’s father, Jimmy Lee Duggar, was already a source of turmoil within the family. In her memoir, Holy Disruptor, released in October 2025, Amy Duggar King, Jim Bob’s niece, sheds light on the dark past. She details the physical and emotional abuse perpetrated by her grandfather, hinting at his possible predatory behavior, drawing parallels to her cousin’s later actions.
Although Amy Duggar King’s book doesn’t delve into this particular aspect, longstanding rumors suggest that Jimmy Lee Duggar served time in prison for fraud during his children’s formative years. Unfortunately, specifics regarding this arrest have become obscured over time, leaving the duration of his imprisonment a mystery.
Josh Duggar was arrested and convicted on child pornography charges
Among the Duggar clan, Josh Duggar, Jim Bob and Michelle’s eldest son, stands out as the family’s most notorious figure. Over the years, he has been embroiled in multiple scandals. In 2015, Josh admitted to molesting his sisters and infidelity. However, it was in 2021 that he delivered a significant blow to the family’s reputation. Following an extensive investigation by the Department of Homeland Security that began with a raid in late 2019, Josh was arrested in April 2021 for possessing and receiving child pornography.
Convicted in December 2021, Josh was sentenced to over 12 years in prison. Despite multiple attempts to overturn his conviction, all appeals have been denied. Currently serving his sentence at FCI Seagoville, Josh claims financial destitution, with his release not scheduled until 2032.
Jana Duggar was taken down to the Tontitown police station, too
In the midst of Josh Duggar’s child pornography trial, news broke that Jana Duggar had had a run-in with the Tontitown Police Department, too. Jana, the second-oldest Duggar child, was charged with endangering the welfare of a child in September 2021.
While Jana stayed quiet about the charge, her sister, Jessa Seewald, took to Instagram to defend her. According to E! News, Jessa revealed that Jana was babysitting when one of the children slipped out unnoticed. Police found the child wandering. Jessa insisted that it was an “innocent mistake” that could have happened to anyone. She did not reveal who Jana was babysitting for at the time, though critics suspect she may have been watching Josh Duggar and Anna Duggar’s children. Jana paid a fine and has since moved on.
Jeremy Vuolo was arrested years before meeting the Duggars
The Duggar family’s troubles with the law seem to extend to their in-laws, too. While the more serious crimes have been committed by Duggar sons, Jim Bob and Michelle Duggar’s son-in-law has seen the inside of a jail cell, too. Years before meeting and marrying Jinger Vuolo, Jeremy Vuolo had a serious run-in with police in upstate New York.
Jeremy, while drunk as a college student, harassed a police officer. Radar Online obtained the 2008 police report, which outlined Jeremy’s drunken behavior, including grabbing at an officer and screaming obscenities. The soccer player turned pastor has discussed the incident in the past, calling it a “wakeup call.” He married Jinger Vuolo in 2016. The couple, who now reside in California, have three children. He’s had no additional legal trouble.
Joseph Duggar and Kendra Caldwell’s arrests are the most recent
The Duggar family is never short on scandals, but the last couple of years, following the release of Jill Dillard’s book in 2023, have been largely quiet. That is, until now. Earlier this week, Joseph Duggar was arrested on charges stemming from a 2020 incident with a minor child. He has been charged with two counts of lewd and lascivious behavior. The victim, now 14, was 9 when the incident occured during a family vacation to Florida. He could spend years behind bars.
While Joseph Duggar’s arrest was shocking, the fact that his wife, Kendra Caldwell, was arrested on unrelated charges days later was even more surprising. Kendra, 27, was arrested on four counts of endangering the welfare of a child and four counts of false imprisonment, according to TMZ. The same charges have been added to Joseph Duggar’s growing list of legal troubles.
Joseph and Kendra’s legal troubles are a developing story.