Sail Of The Century

My latest piece for Ralph Lauren Magazine is on the golden age of sailing. By “golden age,” I mean, of course, the five or so years in the late ’80s and early ’90s when sailing captured the popular imagination, receiving its Hollywood exploitation via the 1992 film “Wind” with Matthew Modine and Jennifer Grey.

The story includes an interview with the usually media-shy legend Dennis Conner, who boasts a fascinating tale of defeat and redemption.

Founded in 1851 and most closely associated with the New York Yacht Club (whose Manhattan clubhouse is one of the city’s architectural gems), the America’s Cup was successfully defended by the US for an astonishing 132 years—still the longest winning streak in sports. That streak ended with Conner’s ignominious defeat in 1983. When redemption came in ’87, it was more than just a victory in sports—it was a patriotic moment befitting a decade that brought the Miracle on Ice and the end to the Cold War.

Conner was a veteran race captain when he took the helm of the Liberty in 1983 and the unthinkable happened. “They just had a faster boat,” Conner tells RL Mag in a rare exclusive interview. “Sometimes you can become so focused on winning that you don’t look at your competitors with an open mind. My competitor [the Australia II, from the Royal Perth Yacht Club] had the new innovation of wings on the keel, something I’d never heard of. I learned that it’s not good enough just to try hard and cover all your bases; that was the lesson I learned from the agony of defeat.”

The loss may have been the best thing that ever happened to the sport of competitive sailing, setting the stage for Conner’s redemptive win four years later. “When I lost the cup in ’83 I was crushed. It was the end of my world. I put the pillow over my head and didn’t know what was next,” he says. “When the chance came to come back from a devastating loss, I just tried to stop feeling sorry for myself and see what I could do about winning it back.”

Check out the full story here. 

(By the way, sailing is on my bucket list. I’ve started preparing by taking the New York Ferry.) — CC

7 Comments on "Sail Of The Century"

  1. Caustic man | May 6, 2018 at 4:00 pm |

    Conner is a legend. The Cup was sailed in San Diego for a while when I was much younger. What fun that was to watch. We were all mad about sailing then.

  2. Bradley Cole | May 6, 2018 at 6:58 pm |


    Okay, I will fill a Teris with a well poured Darl & Stormy and come back to read the full story.

    Cheers, BC

  3. Bradley Cole | May 6, 2018 at 7:02 pm |

    PS Just took the first sip and began reading…. if I ever hear Christopher Cross’ “Sailing” played on a sailboat again, I will jump overboard. BC

  4. sacksuit | May 6, 2018 at 8:50 pm |


    Agreed. Sailing by Christopher Cross has the same effect on me a Loving You by Minnie Riperton.


  5. whiskeydent | May 7, 2018 at 9:40 am |

    Oddly enough, Cross led the best (and most expensive) 60’s cover band working the fraternity circuit when I was in college at Texas. He played our house once and debuted “Ride Like The Wind” a few weeks before it hit the airwaves. We were glad he then returned to Motown.

    CC, don’t forget your floaties.

  6. reppupstateny | May 7, 2018 at 7:00 pm |

    anybody remember this gem?

  7. Great read. Christian I hope you do take up sailing. I have a feeling it will suit you. As a lifelong sailor, I have been privileged to do more than my fair share of it and feel a certain evangelical responsibility to share the experience. Don’t keep putting it off!

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