Baby Bootlegger is perhaps the most beautiful wooden boat ever built. She won the 1924 and 1925 Gold Cup race. The race began as a free-for-all in the early part of the century. However, when the racers developed into overpowered creatures with three and four V-12 engines, the race was changed in the twenties into a class with a requirement for four seats, one engine and a limit on engine size. It was to be a 'gentleman's run-about', and Baby Bootlegger was the pinnacle boat of this group. Today, the Gold Cup race is an unlimited class with Miss Budweiser and other powerful boats.

Baby Bootlegger is a thirty-foot pontoon of varnished mahogany. Except for the open cockpit way in the back, it is an unbroken stretch of mahogany.

Baby Bootlegger had three technological innovations. First, the classic boat design has a 'hard sheer', which means that there's a sharp angle between the deck and the sides of the hull where they meet. Baby Bootlegger was the first boat to have a 'rolled sheer', with the deck smoothly rolling over to meet the hull.

Second, until Baby Bootlegger , the back of the boat was either a straight or wide-vee transome. At the waterline, Baby Bootlegger has a standard transome, but above the water there is a long overhang. This is essentially a large fairing that takes the hull shape back to a sharp point. This combined with the rolled sheer makes the boat look like an upside-down canoe. There are good aerodynamic reasons for this design, but it was seen by many as a matter of styling, and soon after a number of cars were built with varnished mahogany and tulipwood aft-decks: the Stutz Blackhawk, various Hispano-Suizas and Isotta-Fraschinis, Duesenbergs and the Auburn Boattail Speedster.

Third, the rudder was a 4° wedge, like the X-15's controls, instead of the usual airfoil shape, which would wallow in a neutral band of marginal control before it took effect. Not only was this the first application of a wedge rudder on a boat, but also it wasn't until 20 years later that it was tried again.

Baby Bootlegger will do 70 mph flat-out. In addition to being a stunningly beautiful boat, she is considered by many the best handling in any boat.