When bail amounts soar into the billions or even millions, they’re a reminder of wealth, power, and perceived flight risk. Below, we dive into the ten most highest bails ever set and the stories behind these headline-grabbing numbers.
Fast-forward to 2017 in Texas, when Antonio Marquis Willis faced murder charges. The presiding judge admitted she intended to set a $1 million bond—but by “changing the one to a four and adding a bunch of zeroes,” she ended up with a $4 billion bail. Willis’s case became a cautionary tale: even judges can make booming typos that underscore bail’s sometimes arbitrary nature. Even though it was accidental it still was the highest bail ever set.
In 2003, real-estate heir Robert Durst was arrested in Galveston, Texas, for the death of neighbor Morris Black. Labeling him a “serious flight risk” and citing his vast fortune, the judge stunned everyone with a $3 billion bail. Durst’s team argued it was unconstitutional, and it was later slashed to about $450,000. He was ultimately convicted in 2021 and died in prison in 2022 at 78, cementing his story as one of true-crime legend.
In 2005, Ohio courts pegged Kim Freeman—accused of running a sprawling brothel ring—with a $1 billion bail, fearing she’d use international ties to flee to Europe or Asia. Though it later dropped to a more realistic figure, this bond highlighted how bail can be wielded as a blunt instrument against perceived high-risk defendants.
California’s Kening Ma was charged in 2010 for importing modified motorcycles that allegedly violated emissions laws. The judge set Ma’s bail at $150 million (his wife at $75 million), turning an environmental case into a headline about how “green crime” can trigger greenbacks-level bail.
In July 2019, financier Jeffrey Epstein was arrested on charges of sex trafficking minors and granted an unprecedented $100 million bond. To secure it, Epstein had to put up $77 million in collateral—most notably his $56 million New York City mansion. His bail package sparked outrage, as many saw it as a stark example of how wealth can bend the rules. Unfortunately, Epstein died in his jail cell before his trial, and the full saga around his bond and alleged crimes remains shrouded in controversy.
Hedge fund titan Raj Rajaratnam was arrested in October 2009 for orchestrating one of the largest insider-trading rings in history. A New York judge set his bail at $100 million, secured by $20 million in cash and $80 million in liquid assets, including real estate. Rajaratnam’s legal team argued the amount was excessive, but the court insisted it reflected both his wealth and flight risk. He was later convicted and sentenced to 11 years in federal prison, serving seven before release.
In June 2009, Texas financier R. Allen Stanford faced charges for running an $8 billion Ponzi scheme that defrauded investors worldwide. His bail was set at $100 million, backed by a fleet of properties and a luxurious yacht. Stanford’s defense called the bond “unnecessarily punitive,” but prosecutors countered that his resources made him a significant flight risk. Ultimately, he was convicted and sentenced to 110 years behind bars—though he’ll be eligible for parole in 2105.
When Bernard “Bernie” Madoff was arrested in December 2008 for masterminding a $65 billion Ponzi scheme, his bond was set at $10 million. He secured it by pledging multiple properties, including a Manhattan penthouse and Florida estates. At the time, it was one of the largest personal bonds ever, though small compared to later billion-dollar cases. Madoff eventually pleaded guilty and received a 150-year sentence, effectively ensuring he would die in custody.
In November 2003, pop icon Michael Jackson was charged with multiple counts of child molestation and granted a $3 million bond. The bond was secured by several of Jackson’s California properties, allowing him to remain free during his highly publicized trial. Over the course of the proceedings, Jackson maintained his innocence and painted the charges as a tabloid-driven ordeal. He was ultimately acquitted on all counts in June 2005, and the case remains one of the most talked-about celebrity trials in history.
In June 1994, former NFL star O.J. Simpson was arrested on murder charges for the deaths of Nicole Brown Simpson and Ronald Goldman. His bail was set at $250,000, secured by his Brentwood mansion, a relatively modest sum compared to later celebrity cases. The low bond reflected both his celebrity status and the judge’s assessment of his flight risk. Simpson was acquitted in the criminal trial but later found liable in a civil wrongful-death suit, cementing the case’s moniker as “The Trial of the Century.”
From the absurd heights of Antonio Willis’s accidental $4 billion bail to O.J. Simpson’s comparatively modest $250,000, these cases lay bare bail’s extremes. They fuel the ongoing debate over fairness, the presumption of innocence, and whether bail should ever be punitive. So there you have it the top 10 highest bails ever set in U.S. History
