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Criminals who escaped then came back

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Criminals Who Escaped Then Came Back — Daily trivia Friday, August 14, 2026: questions and answers

All 10 questions with answers and explanations. Play this daily

  1. Q 01Which Boston gangster spent 16 years on the run before his arrest in Santa Monica?

    • AWhitey Bulger
    • BRaymond L. Washington
    • CFrank Lucas
    • DBernie Madoff
    Show answer

    Whitey Bulger

    The brine

    Whitey Bulger fled after his FBI handler warned him of sealed indictments, and a renewed FBI appeal centred on his girlfriend, Catherine Greig, finally led agents to him.

  2. Q 02Which drug lord escaped a maximum-security prison through a tunnel from his cell's shower?

    • AJoaquín 'El Chapo' Guzmán
    • BFrank Lucas
    • CAl Capone
    • DPablo Escobar
    Show answer

    Joaquín 'El Chapo' Guzmán

    The brine

    Joaquín 'El Chapo' Guzmán, a leader of the Sinaloa Cartel, made headlines for his elaborate escape in 2015 from Altiplano federal prison via a mile-long tunnel, only to be recaptured in 2016.

  3. Q 03Which bank robber broke out of an Indiana jail, reportedly with a carved wooden pistol, before federal agents killed him?

    • ALucky Luciano
    • BJohn Dillinger
    • CAl Capone
    • DBugsy Siegel
    Show answer

    John Dillinger

    The brine

    John Dillinger's gun was wood by his own account and in FBI files, though a deputy insisted it was real; agents later shot him outside Chicago's Biograph Theater.

  4. Q 04Which serial killer escaped from the Aspen courthouse via a second-story window and was caught six days later?

    • AJeffrey Dahmer
    • BTed Bundy
    • CJohn Wayne Gacy
    • DRichard Ramirez
    Show answer

    Ted Bundy

    The brine

    Ted Bundy escaped again that December, from the Glenwood Springs jail, and fled to Florida, where he murdered at least three more people before his capture.

  5. Q 05Which convicted assassin escaped Brushy Mountain State Penitentiary but was quickly recaptured after a manhunt?

    • AJames Earl Ray
    • BSirhan Sirhan
    • CMark Chapman
    • DCharles Manson
    Show answer

    James Earl Ray

    The brine

    James Earl Ray pleaded guilty to killing Martin Luther King Jr., recanted three days later, and in 1997 King's family backed his call for a trial.

  6. Q 06Which con artist escaped a Georgia county jail, only to be recaptured in New York days later?

    • ABernie Madoff
    • BVictor Lustig
    • CFrank Abagnale Jr.
    • DCharles Ponzi
    Show answer

    Frank Abagnale Jr.

    The brine

    Frank Abagnale Jr.'s Georgia arrest was for ten fake Pan Am checks worth under $1,500, and prison records show he was locked up during much of his famous impostor years.

  7. Q 07Who walked away from an Ohio prison farm after a fatal speeding crash and lived under an alias for 56 years?

    • ABilly Hayes
    • BFrank Freshwaters
    • CGeorge Wright
    • DLeonard Peltier
    Show answer

    Frank Freshwaters

    The brine

    Frank Freshwaters had killed Army veteran Eugene Flynt while speeding in Akron, and after his 1959 walkout he lived under an assumed name until US Marshals found him in Florida.

  8. Q 08Who confessed to being the 'Boston Strangler' but was jailed for unrelated crimes, then escaped from Bridgewater?

    • ADennis Rader
    • BEdmund Kemper
    • CDavid Berkowitz
    • DAlbert DeSalvo
    Show answer

    Albert DeSalvo

    The brine

    Albert DeSalvo was never tried for the stranglings, but in 2013 DNA tied him to Mary Sullivan, the last victim, nearly 50 years after her murder.

  9. Q 09Which 'Houdini of Florida' inmate escaped custody seven times in thirteen attempts, and was recaptured every time?

    • ARobert Stroud
    • BHenri Charrière
    • CMark DeFriest
    • DGary Tison
    Show answer

    Mark DeFriest

    The brine

    Mark DeFriest's four-year sentence, for taking tools his late father left him before the will cleared probate, stretched into decades as each escape attempt added time.

  10. Q 10Which Great Train Robber spent more than three decades on the run before flying home to Britain to be arrested?

    • ABruce Reynolds
    • BBuster Edwards
    • CCharlie Wilson
    • DRonnie Biggs
    Show answer

    Ronnie Biggs

    The brine

    Ronnie Biggs dodged extradition from Brazil because his girlfriend was expecting a Brazilian child, and after flying home he served eight more years.

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