Money buys speed, but not immunity. These mugshots of wealthy people swap penthouses and press teams for a bare wall, a placard, and a minute nobody plans for. Some smiled, some scowled, but all of them paused for the same camera.
Scroll on for this set, where fortunes met the booking desk and the headlines wrote themselves.
1. John McAfee
The antivirus pioneer was arrested multiple times late in life, including a high-profile custody in Spain in 2020. His legal troubles and fugitive stretches turned him into a headline magnet.
2. Tiger Woods
The golf superstar was booked in Florida in 2017 after a roadside stop tied to prescription medications. He later pleaded to a lesser charge and entered a diversion program.
3. Mike Tyson
The heavyweight champion’s most famous booking followed his 1992 rape conviction. He served prison time and returned to the ring years later.
4. Patty Hearts
The newspaper heiress was arrested in 1975 after joining the SLA and participating in a bank robbery. She was convicted in 1976, had her sentence commuted, and was later pardoned.
5. Robert Durts
The real-estate heir cycled through arrests for weapons and murder cases across decades. He was ultimately convicted in 2021 for killing Susan Berman.
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6. Leona Helmsley
The hotel magnate dubbed the “Queen of Mean” was booked in the late 1980s for tax evasion. She was convicted in 1989 and served a prison term.
7. Bernie Maddoff
He was arrested in 2008 for running a record-breaking Ponzi scheme. He pled guilty and received a 150-year sentence.
8. Conrad Black
The media baron was booked in 2005-2007 on charges of fraud and obstruction. He was convicted and later received a partial presidential pardon.
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9. Justin Bieber
The pop star’s 2014 Miami booking followed a traffic stop and DUI arrest. The image became one of the era’s most viral mugshots.
10. Harvey Weinstein
The producer was booked in 2018 amid multiple sexual assault cases. He was later convicted in Los Angeles. His New York conviction was overturned on appeal.
11. Teresa Giudice
The reality TV figure was arrested in 2013 on fraud charges. She pleaded guilty and served time before returning to television.
12. Tom Delay
The former House Majority Leader posed for a famous smiling Texas mugshot in 2005 after an indictment. His 2010 conviction was later overturned on appeal.
13. Allen Iverson
The NBA superstar surrendered to Philadelphia police in July 2002 on gun and assault charges. A Municipal Court judge later dismissed all counts.
14. Connor McGregor
The UFC champion has been booked multiple times, including a 2018 arrest in New York for a bus incident and a phone case in 2019 in Miami. He kept fighting and also making news.
15. Ja Rule
The rapper was booked on a 2010 gun case and later for tax issues. He served time and returned to music and touring.
16. Bill Gates
The Microsoft cofounder’s famous 1977 New Mexico mugshot came after a traffic stop. It’s a rare early-life image that still circulates widely.
17. Charles Ponzi
The namesake of the Ponzi scheme was arrested in 1920 for mail fraud. He served time and was eventually deported.
18. Paul Manafort
The political operative was booked in 2017-2018 on tax and bank fraud charges and was convicted. He later received a presidential pardon.
19. Andrew Luster
The Max Factor heir fled mid-trial but was captured and booked in 2003. He was convicted of multiple counts related to drugging and assault.
20. Bill Cosby
The comedian was booked in Pennsylvania and convicted in 2018. The conviction was later overturned and he was released. This legal saga reshaped his entire legacy.
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These faces show how power and PR can’t outtalk a mugshot. If this scratched your pop-culture itch, keep the scroll going with these 25 Photos That Sum Up the End of the 20th Century or these 19 Photos of Famous Actresses from the 1960s-1980s. You can also take a look at these 15 Overlooked Stories About Actors from the Late 1900s.
