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The last brokered conventions of the parties

JumpinJack

JumpinJack

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For Democrats, that was in 1952 when it took three ballots to nominate Illinois Governor Adlai Stevenson. The GOP's last multi-ballot convention occurred four years earlier in 1948. New York Governor Thomas Dewey won that one, also after three ballots.
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A Brokered Convention in 2016: Why It Might Happen, What It Might Mean | RealClearPolitics

Hmmm....Adlai Stevenson for the Dems, and Dewey for the Repubs in brokered conventions. Stevenson lost in a landslide to Dwight Eisenhower (a moderate Republican who considered running on the Democratic Party ticket; he won in part because he courted the female vote, which had never been done before). Dewey famously lost to Truman, of course.

Interestingly, when each lost, his opponent who won, also went on to lead his party to take controll of the Senate and House, as well (Dwight Eisenhower led the Republican takeover, and Truman led the Democratic takeover).
 
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