Bob Bernstein

Bob Bernstein – Rhodes 19 Treasure

I was recently doing some class history work—looking at past nationals results to get them updated for the website. In looking back through early years’ results, the earliest name I recognized was Bob Bernstein’s, whom I know from racing more recently in last year’s nationals. From 1973 to 2015 is quite a span of participation in the Rhodes class, and I figured there was a good story there—and I sure was right. With the very significant help of Bob’s wife, Joanne, and Bob’s friends, I put together a short sketch of Bob’s adventures over the years. Bob is a class act and one of the Rhodes 19’s class treasures.

Bob started sailing back when he was one year old. His family had an old wooden boat named Flight— well, certainly it is very old now, but it is still on the same mooring in Montrose Harbor in Chicago. Bob learned about sailing and racing on that boat. He and his dad won boat of the year at least once, and the boat was sailed in the Mac when Bob was away at summer camp.

In about 1973, that boat was sold and Bob bought his first Rhodes, #2000. Bob’s first nationals was in 1973 in New Bedford, Massachusetts. One of his first crew was Scott Graham, who later became a notable naval architect with Eric Schlageter in the firm G&S. During those years, Bob won the Chicago fleet championship several times and competed in several nationals, always placing well. Bob’s friend and competitor Elliott Lyon, who sailed both against and with Bob in the ’70s and ’80s, says Bob was “the smartest guy on the water I could possibly imagine.” Bob would often crew on other boats as well—with a big positive impact on their performance. In Elliott’s last race, with Bob as crew, they clawed their way back from sixth to first in one of those Zenlike moments.

Bob’s seamanship is impressive as well; during the 1979 nationals in San Francisco, the hellacious winds and conditions capsized six boats in a single race. Meanwhile, Bob, his rudder having broken off, was able to steer his boat to safety using sails and weight alone.

Bob sold his boat in the ’80s and for some years pursued other yachting adventures. In the mid-to-late ’80s, Bob crewed on a friend’s boat out of Jackson Harbor on Chicago’s South Side. One summer the friend was on holiday for a month, so Bob, looking for another boat to sail on, answered an ad from Dorsey Ruley, who had an about-forty-foot racing boat and was looking for a helmsman and tactician. Needless to say, Bob was very curious as to why an owner wanted someone else to sail his boat. Dorsey couldn’t sail the boat himself because he is a quadriplegic. Being out on a sailboat, strapped into a special seat at the back of the boat, is when he really enjoys himself. While in Australia with his wife in 2000, Bob checked out a boat in Sydney for Dorsey, which Dorsey then bought. Bob drove them to first place in the 2002 Mac race and has won boat of the year numerous times. Bob has been sailing with Dorsey for about twenty years now.

Meanwhile, Bob really missed small-boat sailing, so Joanne kept encouraging him to buy one again. He said he would do so only if he could find one that was in great shape and competitive. After a year or two, he found his boat; Chris Small in Marblehead had just beautifully refinished it. Bob flew out to see it six or so years ago in about March, and then in late April or early May, Joanne and Bob drove from Chicago to Marblehead to trailer it back.

When he was looking to buy a boat, Bob often said that Rhubarb, Bob Jensen’s boat, was the boat to try to beat. Bob Jensen was Bob Bernstein’s legendary competition, and he was an inspiration! Bob was saddened when Bob Jensen retired. When I asked Bob Jensen about Bob, he said he was a worthy competitor and one with a remarkable ability for analyzing and anticipating weather patterns. Bob Jensen always had his eye on Bob’s whereabouts on the racecourse.

Upon returning to Fleet 12, he has become one of its most helpful and instructive members. He has run seminars and on-water clinics to upgrade the Chicago fleet’s performance, and he took on chairing the 2016 nationals. Chicago wouldn’t be hosting them if it weren’t for Bob. Also, once or twice a season, usually in the spring, he helps other Rhodes sailors who request his help on a practice day. On those days, he’ll jump from boat to boat and work with three or so boats each day.

Professionally, Bob had a seat on the CBOE (Chicago Board of Options Exchange) for about sixteen years. After he left the floor of the exchange, he continued to do some trading from his computer, but he never passes up a doubles tennis game, something he does with about the same intensity as he sails. He plays three to six times a week, less often during sailing season than in the winter. Bob also works part time as a financial adviser. He works independently and likes to look at the whole financial picture of his clients so he can help them holistically.

In any event, I’m told that Bob has been a Chicago Corinthian YC member for seventy years. How lucky for the club.

By Steve Uhl