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Illustration by Mark Steele of Wayne Allyn Root running for president in 2024
Mark Steele

Wayne Allyn Root ’83CC, professional sports prognosticator, gives the following picks: John McCain will beat Barack Obama; the Colts will meet the Cowboys in this season’s Super Bowl; and in 2024, Root himself will occupy the Oval Office.

“I plan on being the president of the United States in 16 years,” Root says from his 7000-square-foot home in suburban Las Vegas. “People laugh at that, but I’m going to do it.”

Predicting the future is not an exact science, but it is good business. As founder and chairman of the publicly traded sports handicapping company Winning Edge International, Root sells his sports picks — Guaranteed Winners! — for as much as $25,000 for a season package. While those in the gambling business call him a tout, Root prefers oddsmaker. America’s oddsmaker.

“The type of person who gambles on sports, gambles on business,” he says. “When business closes at 5 on Friday, they all go to Wayne Root. I am the Merrill Lynch of the weekend.” (This comparison was made shortly before Merrill Lynch was bought by Bank of America.)

These days, however, Root is diversifying: he’s the Libertarian Party’s candidate for vice president of the United States.

Root’s specialty might be football, but politics is his passion. By his estimation, though, politics is harder to predict. The rise of Barack Obama to national prominence, for example, would have been hard to foresee five years ago, before Obama gave the keynote address at the 2004 Democratic convention. When the Columbia College Class of 1983 met for its 20th Reunion it was Root, not Obama, who was asked to speak as part of a panel of distinguished alumni.

Like his running mate, former Georgia congressman Bob Barr, Root was previously a lifelong Republican. His political hero was Barry Goldwater; he named his youngest son Remington Reagan; and in 2005, he authored Millionaire Republican: Why Rich Republicans Get Rich — and How You Can Too! But his “libertarian awakening,” as he describes it, began when the federal government banned online gambling in 2006. Runaway federal spending and the ballooning deficit only hastened the conversion. Root’s issues are economic and personal freedom, and he says his experience as a fast-talking self-promoter, radio and TV personality, author, and small-business owner will serve him well in higher office.

“I’m someone who believes very strongly that all politicians are entertainers and salesmen,” he says.

Since his nomination in May, when he was introduced to the Libertarian convention by his 16-year-old daughter Dakota, Root has spent most of his time giving radio interviews, hoping to connect with disaffected Republicans and begin his quest for the White House. His goal is to win three to seven million votes in November.

Those numbers aren’t exactly Obamian, but Root nonetheless draws parallels between himself and the Democratic nominee. Both came from modest beginnings. The son and grandson of butchers, Root grew up in a two-family home he shared with his grandparents in Mt. Vernon, New York, where he was “the only Jewish kid in an Italian neighborhood surrounded by an all-black town.” He began at Mt. Vernon High School and then transferred to the Thornton-Donovan School, a private school in nearby New Rochelle. Growing up, Root wanted to succeed Jimmy the Greek as the biggest personality in oddsmaking. He made a local name for himself in a 1977 profile in the Mt. Vernon Daily Argus of his betting abilities when he claimed a success rate of 73 percent.

For a brief time, Obama’s and Root’s paths did cross. They both majored in political science at Columbia, but their lives diverged sharply after they graduated in 1983. Obama became a lawyer and moved to Illinois, where he married a fellow lawyer; Root followed his entrepreneurial spirit to Nevada, where he started a gambling business and married a former Miss Oklahoma. Debra and Wayne Root now have four children, including an infant, Contessa Churchill. In 2006, Root joined previous honorees such as Wayne Newton and Sammy Davis Jr. in being inducted into the Las Vegas Walk of Stars. If Obama has the audacity of hope, Root simply has audacity.

“We are the greatest dichotomy that has ever run for president and vice president of America who happened to be in the same college class,” he says.

So 25 years later, their lives have intersected again. Both candidates’ runs could be viewed as historic firsts. Barack Obama is the first African American to win the nomination for the presidency of a major political party. Wayne Root, meanwhile, points out that he is “the first dad with home-schooled children in modern political history to be on a ticket.” And, he adds, the first Nevadan.

And while he’d settle this year for vice president, Root isn’t betting on it. He has his eye on the long term.

“I’m the most qualified person in the world,” he says, “to end government as we know it.”