Think You Know Steinbrenner? Take This Yankees Boss Quiz Now!

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  • 1/10 Questions

    Who was George Steinbrenner most famously associated with owning?

    • New York Yankees
    • Boston Red Sox
    • New York Mets
    • Los Angeles Dodgers
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About This Quiz

T’s the bottom of the 9th, your trivia team is down by one, and someone drops the million-dollar question: "Who reshaped the Yankees into a baseball dynasty?" You freeze. The room waits. Your sports pride is on the line.If you’ve ever felt the panic of forgetting a name you swear you knew, this George Steinbrenner Quiz is your redemption.

From fiery front-office feuds to World Series comebacks, the George Steinbrenner legacy is packed with the kind of drama that makes baseball more than a game. This quiz doesn’t just test memory—it tests your understanding of what made “The Boss” an icon in American sports culture.

Disclaimer: This George Steinbrenner Quiz is designed for educational and entertainment purposes only. While it draws on real historical facts about George Steinbrenner’s life and leadership, it is not affiliated with any official sports organization. Take it for fun, learning, or bragging rights—just don’t bet your fantasy league on it.

Think You Know Steinbrenner? Take This Yankees Boss Quiz Now! - Quiz

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  • 2. 

    What was Steinbrenner’s nickname in the media?

    • The General

    • The Boss

    • The Coach

    • The Commander

    Correct Answer
    A. The Boss
    Explanation
    Steinbrenner earned the nickname “The Boss” for his authoritative and often aggressive management style. He was known for directly involving himself in decisions related to players, managers, and team strategy. This nickname became iconic in sports journalism, representing his larger-than-life presence in baseball. None of the other nicknames had cultural traction or relevance to his persona.

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  • 3. 

    In what year did Steinbrenner purchase the Yankees?

    • 1968

    • 1973

    • 1980

    • 1990

    Correct Answer
    A. 1973
    Explanation
    George Steinbrenner bought the Yankees in 1973 from CBS for just under $10 million. This purchase marked a turning point for the franchise, initiating an era of intense investment, branding, and championship pursuits. The other dates do not align with historical fact; 1980 and 1990 reflect years of significant Yankees events but not ownership acquisition.

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  • 4. 

    Which profession did George Steinbrenner initially pursue?

    • Law

    • Education

    • Navy Officer

    • Business Executive

    Correct Answer
    A. Business Executive
    Explanation
    Before his sports empire, Steinbrenner was a successful businessman and worked in the shipping industry. He was also involved with Kinsman Marine Transit, a Great Lakes shipping company owned by his family. While he had experience in other areas like education and briefly served in the U.S. Air Force, his major pre-Yankees identity was that of a business executive.

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  • 5. 

    How many World Series titles did the Yankees win under Steinbrenner?

    • 5

    • 7

    • 4

    • 6

    Correct Answer
    A. 7
    Explanation
    The Yankees secured 7 World Series championships under Steinbrenner’s ownership, spanning from 1977 to 2000. His aggressive management, frequent roster changes, and enormous investments in talent contributed to these victories. While options like 5 and 6 represent partial truths for certain decades, only 7 accurately reflects the total during his reign.

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  • 6. 

    Steinbrenner was temporarily banned from MLB for what reason?

    • Cheating in contracts

    • Drug violations

    • Paying a gambler for dirt

    • Insider trading

    Correct Answer
    A. Paying a gambler for dirt
    Explanation
    In 1990, Steinbrenner was banned from MLB after admitting to paying a known gambler, Howard Spira, for damaging information about Dave Winfield, one of his star players. This move was highly controversial and marked one of several times Steinbrenner clashed with league officials. The other choices don’t match the factual reason for his suspension.

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  • 7. 

    Which reality TV show featured Steinbrenner’s company ship?

    • Shark Tank

    • The Apprentice

    • Undercover Boss

    • Celebrity Apprentice

    Correct Answer
    A. The Apprentice
    Explanation
    Steinbrenner’s yacht company appeared on the reality show “The Apprentice,” hosted by Donald Trump. The connection served as a branding opportunity and reinforced Steinbrenner’s reputation for business acumen and high-stakes decision-making. “The Apprentice” was known for showcasing elite business personalities, making it a perfect fit for his image.

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  • 8. 

    What trait was George Steinbrenner most known for with managers?

    • Long-term mentorship

    • Frequent firings

    • Total delegation

    • Lack of involvement

    Correct Answer
    A. Frequent firings
    Explanation
    Steinbrenner was infamous for his tendency to fire and rehire managers, especially Billy Martin, whom he let go and rehired multiple times. This revolving-door management style became a hallmark of his reign. He expected immediate results and had little patience for underperformance, setting him apart from most long-term-focused owners.

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  • 9. 

    Steinbrenner was portrayed as a character in which sitcom?

    • Friends

    • Seinfeld

    • The Office

    • Frasier

    Correct Answer
    A. Seinfeld
    Explanation
    In the sitcom Seinfeld, Steinbrenner was portrayed as George Costanza’s eccentric boss at the Yankees. Though Larry David voiced the character, the portrayal was intentionally absurd and became one of the show's recurring jokes. It captured Steinbrenner's reputation for being unpredictable and over-the-top, making it culturally iconic.

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  • 10. 

    What was Steinbrenner’s background before sports ownership?

    • Professional athlete

    • Construction magnate

    • Broadway producer

    • Talent agent

    Correct Answer
    A. Construction magnate
    Explanation
    Before owning the Yankees, Steinbrenner built his fortune in the shipping industry, managing his family’s business. He later branched into real estate and other ventures, becoming a self-made construction magnate. This background gave him the capital and leadership foundation that later defined his high-profile sports ownership.

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Quiz Review Timeline (Updated): Jun 8, 2025 +

Our quizzes are rigorously reviewed, monitored and continuously updated by our expert board to maintain accuracy, relevance, and timeliness.

  • Current Version
  • Jun 08, 2025
    Quiz Edited by
    ProProfs Editorial Team
  • Jun 02, 2025
    Quiz Created by
    Hansika

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