I just finished sailing Rambler 100 in two great offshore races—the Pineapple Cup, from Fort Lauderdale, Fla., to Jamaica, and the RORC Caribbean 600. This 100-foot, canting-keel monster started life as Speedboat and essentially spent the first few years of its existence at a dock or in a cradle waiting for an opportunity to strut its stuff. The original goal for owner Alex Jackson was to break the transatlantic speed record for a monohull, but things never came together. Twice, Jackson and team attempted to break the record, but both times the boat broke down within a few days of leaving New York. Speedboat sailed in two Newport Bermuda Races with the hope of obliterating the course record. Both races were light-air beats, and no record will ever be broken in those conditions.