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New York gubernatorial election, 1994
The New York gubernatorial election in 1994 was perhaps one of the most-watched races throughout 1994, a function of the candidates involved. Incumbent Governor Ron Brown, the first African-American governor elected in the United States since Reconstruction, was a relatively weak incumbent owing to sluggish growth in the Empire State and the national anti-Democratic mood. Brown's historic status and closeness with the party establishment made him one of the top targets for the Republican Party going into 1994. Congressman Joseph J. DioGuardi, rather than seek a sixth term, became the presumptive front-runner for the campaign. However, another high-profile New Yorker that the Republican Party had been seeking to recruit for high office in the future brashly announced his candidacy: real estate mogul Donald Trump. Trump had veered from a Republican to a "Huddleston Democrat" over the president's Secure Borders Act and then back to the GOP over the administration's negotiations with the weakened Soviet Union. Several prominent New York Republicans had urged Trump to consider running for office in 1996. Trump, however, both disliked Brown and needed more publicity after a series of investments in New Jersey failed and so declared his candidacy for governor.

Despite high name recognition, Trump’s self-aggrandizing tendencies, lack of political experience and penchant for outrageous remarks set the party establishment against him, even as his law-and-order stance and his calls for "a stronger 'Secure Borders Act'" proved popular with the party grassroots. DioGuardi ended up winning the Republican nomination handily- but the Conservative Party of New York then named Trump as their candidate, ensuring that Trump would remain on the ballot in November and splitting the right-wing vote.

Brown, who later recalled that if the Conservatives had endorsed DioGuardi, would likely have lost his bid for re-election, ran a remarkably subdued campaign. Trump's outrageous statements and antics resulted in national media attention and DioGuardi watched with horror as Trump overtook him for second place against Brown. Briefly, Trump and Brown were neck and neck- but a live microphone caught Trump making racially insensitive remarks in early October and the mogul's numbers fell. DioGuardi gained enough soft Trump voters to break 20%, but Trump still ran way ahead of him- into a distant second behind Brown.

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The electoral results would have national consequences. Brown's victory would ensure that he would remain politically viable for Dick Gephardt to pick him as a running mate in 2000, the first African-American on a major party ticket. The subsequent rightwards drift of the New York Republican Party in order to prevent the Conservatives from nominating their own candidates and splitting the vote resulted in New York becoming even less competitive on a federal level, resulting in Democrats controlling all but three members of the state's congressional delegation by 2017. As for Trump, the loss embittered the real estate developer towards elected office, and briefly resulted in a downturn in his finances— although by the start of the new millennium, Trump’s net worth would be higher than it ever was as memories of the election began to fade.

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