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Watch Episode 3 of The Contenders — 16 for '16

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Why you should care

Because you can’t understand today’s candidates without listening to yesterday’s.

Learn more about the men and women who have run the ultimate political gauntlet in pursuit of the most powerful job on Earth by watching THE CONTENDERS: 16 FOR ’16, a new TV series from OZY airing every Tuesday at 8 p.m. EST this fall on PBS.

Harvard-trained lawyers and successful governors of Massachusetts, Michael Dukakis and Mitt Romney were two of the most competent contenders ever to run for President. But both men found themselves utterly unprepared to combat the portraits their opponents painted of them and to define themselves successfully to the American public.

Following the Democratic convention in the summer of 1988, Dukakis was leading his Republican rival George H.W. Bush by 17 points and looked like he was on track to become the next president of the United States. The son of Greek immigrants, Dukakis had made a reputation for himself as an incorruptible leader and efficient administrator, one who had architected the “Massachusetts Miracle” in his home state over his three terms as its governor.

Despite not having the soaring oratory skills or blinding charisma of many successful presidential candidates, Dukakis and his well-organized campaign emerged from a crowded Democratic field in 1988 to win the nomination. In the fall of that year, after the convention though, Dukakis would bear the brunt of one of the dirtiest negative ad campaigns in presidential history, including the infamous “Willie Horton” spot. The governor did not help himself by declining to respond in kind to the attacks or to quit his day job in order to spend more time on the campaign trail and, as a result, would carry only 10 states and lose to Bush by around 7 million votes.

Despite having two parents involved in public service, Mitt Romney did not rush into public life himself until after a longstanding career in business. For much of that time, Romney worked for Bain and Co., a Boston-based consulting firm, later becoming the CEO of a spin-off private equity firm Bain Capital. After amassing a personal fortune estimated to be as high as $250 million at Bain, Romney entered the political realm in 1994 with a failed run against Sen. Ted Kennedy before winning the 2002 gubernatorial race in Massachusetts, where under his leadership, the state would become the first in the nation to enact a universal health care system.

Romney’s first run for the presidency came in 2008, when he would spend about $45 million of his own fortune toward the goal. He would win 11 primary contests but finish well behind the Republican party’s ultimate nominee, Sen. John McCain of Arizona. In 2012, Romney would win the party’s nomination, however, becoming the first Mormon ever selected as a major party nominee, before falling to Barack Obama’s re-election campaign, which successfully painted him as a wealthy businessman out of touch with the lives of ordinary Americans.

OZY2016

The route to the White House: news, stories and analysis from on and off the presidential campaign trail.