Democratic Presidential Contender Jim Webb Once Boxed Oliver North

He may not win the presidential election, but Webb cannot be beaten.
October 14, 2015, 6:20pm
Photo by Joe Raedle/Getty Images

Jim Webb is a strange and singular human being. He's a Vietnam veteran with a Silver Star, a Navy Cross, and a Purple Heart. He's a former Democratic U.S. senator and Secretary of the Navy under Ronald Reagan. He's written 10 books, including six novels, and an editorial for Washingtonian Magazine titled, "Women Can't Fight." He's an award-winning journalist and the executive producer of the Samuel L. Jackson/Tommy Lee Jones movie Rules of Engagement. He became the world's first known beneficiary of a YouTube video going viral when his opponent during the 2006 Virginia senate race, incumbent George Allen, was caught on camera calling a Indian-American Webb staffer "macaca." He once called out President George W. Bush to his face during a White house meet-and-greet and admitted he was tempted to "slug" the president for getting the country involved in Iraq. Webb also has a strange affection for the Confederacy and has defended the South's desire to secede from the union.

Oh, and once he boxed disgraced Marine Colonel and Iran-Contra fall-guy Oliver North. Jim Webb is strange and singular.

Strangest of all, though, is this: Apparently Jim Webb is running for president. As a Democrat, no less. You'd be forgiven for thinking Hillary Clinton and Bernie Sanders were the only two candidates in that race, but sure enough there was Webb last night onstage at the first Democratic debate in Las Vegas, acting like a real candidate with a real chance to win the nomination.

Not that he does. And not just because his name isn't Hillary Clinton and not just because he's currently polling at 0.8% and not just because he's a moderate Democrat running in the age of Bernie Sanders and not just because he's obsessed with an impending cyber-war with China and not just because the enemy he says he's most proud of having made during his political career is a grenade-wielding Viet Cong soldier he shot dead in July 1969 and not just because he's defended the fucking Confederacy's right to secede from the fucking United States. Jim Webb can't win the nomination because no one cares about Jim Webb. A point illustrated by the fact that Webb spent the majority of his meager speaking time last night complaining about the fact that he wasn't being given more speaking time. It's a vicious political circle Webb is caught in: No one's paying attention to him because he's not doing well in the polls, and he's not doing well in the polls because no one's paying any attention to him. So Webb responded by going into full-crank mode, repeatedly lashing out at moderator Anderson Cooper and demanding more airtime. Cooper lashed back but Webb was undeterred. Jim Webb is never deterred. He kept railing, unacknowledged, like Willy Loman or Lear on his heath.

See, Jim Webb is not just strange and singular; he may be insane. But you can't say he's not a fighter. He's a fighter all the way. Even in—especially in—futile contests. In Vietnam, in George Bush's White House, in Hillary Clinton's Wynn resort.

So it fits that in 1967 young James Webb took on Oliver North in an intramural boxing championship bout. The story of the fight, like the story of Jim Webb, is strange and singular. North had been involved in a car accident during his freshman year, leaving him with a serious head injury. So when he got out of the hospital and started boxing he had an advantage over his opponents at the academy because they were all scared of punching North in the head. During one fight, a young man caught North in the face with a jab and North fell to the ground. He got up before the referee's count was done but his opponent was so shaken by the experience he nearly fainted in the ring.

Oliver North continued his strange and singular boxing career, and in 1967 he faced James Webb for the 147-pound Academy championship. Webb would later recall that he was sick even thinking about fighting North. There had been two deaths that year in collegiate boxing, and Webb dreaded the idea of fighting anyone with a head injury.

"I found it so distasteful that I don't even want to talk about it today," Webb would say 20 years later. Yet he fought. Yet another futile contest.

North would defeat the tentative Webb by decision. The next year the Annapolis boxing coach asked North to stop boxing and made him an assistant coach. Webb, meanwhile, went on to fight in Vietnam and, upon returning, started his writing career. He included a boxing scene in his second novel, A Sense of Honor, about life as a plebe in the Naval Academy, that some say was based on his fight with North. A young man named Chervanek is beaten and bloody and against the ropes, but when his opponent steps into to finish him off Chervanek miraculously leaps forward—bleeding, one eye closed—and knocks the other man out.

Contrary to rumor, Webb has always said the Chervanek character was not based on North. North, Webb said, never knocked him off his feet. No one ever knocks Jim Webb off his feet. Not Oliver North, not George Bush, not Hillary Clinton, not the Viet Cong, and certainly not Anderson Cooper. Even when he loses, Jim Webb wins.