How to Use bootlegger in a Sentence

bootlegger

noun

• His father, Elmo, was a cotton farmer and bootlegger who did time in jail.
  — Richard Cromelin, Los Angeles Times, 28 Oct. 2022
• His father was a factory worker and a barber, as well as a bootlegger and loan shark.
  — Gary Baum, HollywoodReporter, 2 Apr. 2026
• The author also learned that her grandfather was a bootlegger.
  — Myrna Petlicki, Chicago Tribune, 17 Nov. 2022
• His death reportedly was the result of a dispute with a bootlegger.
  — Kori Rumore, Chicago Tribune, 21 Mar. 2026
• Jimmy Tallant is a local bootlegger whose father led the mob.
  — Sam Sacks, WSJ, 28 May 2021
• Gosha, a local station master, has a side-hustle of his own, turning a blind eye while bootleggers siphon diesel from the tankers that sit idly on the train tracks.
  — Damon Wise, Deadline, 11 July 2026
• And Bootlegger Cove is named for the many bootleggers who landed their wares south of town to avoid detection.
  — David Reamer | Alaska History, Anchorage Daily News, 23 July 2023
• Even the underground tunnels bootleggers used to service the Green Mill during its speakeasy days are still in place.
  — Meena Thiruvengadam, Travel + Leisure, 8 Apr. 2026
• That man, Bryant said, is her grandfather, who earned his keep as a bootlegger during prohibition.
  — Matthew Adams, Fort Worth Star-Telegram, 26 Aug. 2025
• The granddaughter of a bootlegger grows up to be an upstanding citizen and a minister’s wife.
  — Matthew Adams, Fort Worth Star-Telegram, 26 Aug. 2025
• Prohibition also took hold in Indiana during the decade, though bootleggers did pop up across the state.
  — Joe Mutascio, IndyStar, 17 Oct. 2025
• The Oregon Journal published the mugshots of a former local bootlegger and two other ex-cons.
  — oregonlive, 24 Sep. 2021
• Nearly every show from the 1974 tour was captured by bootleggers, but this box set is the first chance to hear most of them with pristine audio.
  — Andy Greene, Rolling Stone, 6 Sep. 2024
• Stock car racing's origins trace back to the Prohibition era when bootleggers raced modified cars.
  — Keith Laing, USA Today, 23 May 2026
• The bootlegger was framed — really — by none other than Chicago Outfit boss Al Capone.
  — Kori Rumore, chicagotribune.com, 17 Mar. 2022
• Roman Gorsky is the Gatsby figure, not a bootlegger but a fantastically wealthy arms dealer.
  — Thomas Mallon, The New Yorker, 27 Feb. 2023
• Kentucky's vast wilderness and mountainous regions served as hideaways for bootleggers, Rein said, while the government used paid informants to sniff them out.
  — Maggie Menderski, Louisville Courier Journal, 16 Sep. 2025
• Childhood friends, Costello and Genovese thrived as bootleggers during Prohibition and rose to the upper ranks of the mob.
  — Bilge Ebiri, Vulture, 21 Mar. 2025
• Sharon Stone co-stars as a mob boss with a few screws loose — her gang of bootleggers toggles with Hutch, threatening to ruin everyone’s R&R.
  — Brent Lang, Variety, 15 Aug. 2025
• For a time it was owned by George Remus, a notorious bootlegger, but the sixth generation Pogues now distill the small-batch bourbon here.
  — Caroline Eubanks, Condé Nast Traveler, 23 Sep. 2022
• The island harbors plenty of secrets, too, like long-ago drunken parties in a notorious inn, and bootleggers stashing bottles in Peddocks' coves.
  — Madeline Bilis, Travel + Leisure, 10 Aug. 2023
• In the 1920s, Moonlight Beach was popular with sunbathers, race-horse aficionados and bootleggers, who used the beach as a hooch drop-off point.
  — San Diego Union-Tribune, 2 Oct. 2023
• Apparently, Hayward once threw a 72-hour-long cook-off, was a part-time bootlegger (possibly for his own consumption), and played epic, high-stakes poker games.
  — James Tarmy, Bloomberg.com, 19 Aug. 2020
• At the dedication ceremony, Ferlinghetti mentioned that the dead-end alley was once used by bootleggers and undertakers, and that a poet could hang with that crowd.
  — Sam Whiting, San Francisco Chronicle, 23 Feb. 2021
• And follow along on NASCAR’s journey, from its bootlegger beginnings to its billion-dollar rise to the top of the sports world.
  — Bill Bootz, Charlotte Observer, 23 Dec. 2025
• From embracing bootleggers to pulling its catalog from Spotify, Mackenzie explains how the band has tried to protect its creative core while the industry transforms around it.
  — Charlie Warzel, The Atlantic, 13 Feb. 2026
• Counterfeit merchandise has long been a problem for musicians, with suppliers and artists now contending with new school online retailers and old school bootleggers hawking wares outside of concerts.
  — Jon Blistein, Rolling Stone, 9 Sep. 2025
• Key lime pie has been enjoyed by locals in Key West for over 100 years, which means bootleggers and Ernest Hemingway both (most likely) indulged in the sweet-tart treat.
  — Kaitlyn Yarborough, Southern Living, 28 Dec. 2025
• Their bourbon, the Alice Brown, is named after a female bootlegger who lived in Lanesville, Indiana, during prohibition.
  — Maggie Menderski, The Courier-Journal, 4 Jan. 2023
• Set along the Mississippi coast in the 1920s, the story traces the unlikely friendship between a bootlegger’s wife and a young woman fleeing violence.
  — Kaitlyn Yarborough, Southern Living, 1 Feb. 2026