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‘Jeopardy!’ Contestant Has Big Win After Taylor Swift & Drake Question

Madeline Kaplan won with $38,400 after betting everything on a Final Jeopardy clue about Taylor Swift, Drake and another singer.

  • On Tuesday, May 5, 2026, editor Madeline Kaplan won Jeopardy! after correctly identifying a Final Jeopardy clue about Taylor Swift, Drake, and Morissette, finishing with $38,400.
  • Kaplan, from Toledo, Ohio, competed against Jeremy Roberts of Midhurst, Ontario, and Shannon Crisenbury of St. Clair, Michigan, entering her second game with $31,700 in accumulated winnings.
  • Kaplan found a Daily Double on clue 11 to reach $4,000, while Crisenbury secured the first Double Jeopardy Daily Double on clue three, holding a $19,200 lead by round's end.
  • The final clue under The Canadian Album Charts category asked which singer tied Swift and Drake for the most number one albums on the Billboard Canadian Albums chart, with 15.
  • Kaplan correctly responded, "Who is Morissette?", while Roberts answered, "Who is Celine Dion?". Roberts finished with $10,000 and Crisenbury ended with $3,400 after wagering $3,000.
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Hastings TribuneHastings Tribune
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‘Jeopardy!’ Contestant Has Big Win After Taylor Swift & Drake Question

Back-to-back Daily Doubles secured the win.

·Nebraska, United States
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Rockdale Citizen & Newton Citizen broke the news in Georgia, United States on Tuesday, May 5, 2026.
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