Bob Gailen, a long-time friend, gifted graphic designer/artist, and sailing partner passed away last Monday, at the age of 71. I want to express my deepest condolences to Carol, Hannah, Winnie, and the rest of his loved ones.,
Bob was perhaps the single greatest influence in my life at the time and the person I considered my best friend in the early years after I moved to Chicago nearly four decades ago. His even temperament, keen observations, creativity, and wisdom helped me find my way in many senses of the word. We spent countless hours every weekend on Lake Michigan aboard the Blueline. We could go the better part of the day, just the two of us aboard, without saying a word to each other and yet we shared a special connection as we skimmed across the water, each doing our job and having supreme confidence in the other person doing theirs. There were plenty of times, especially Wednesday nights, racing in the Chicago Yacht Club Beer Can Regatta when the boat would be filled with guests serving as crew. Secretly, Bob and I always agreed it was the most fun when it was just the two of us. Some days, when the winds were dead, we'd just drop anchor or drift for hours and talk about life. Bob wasn't into macho guy talk, and his humble nature kept him from focusing the conversation on himself. Those conversations remain some of the fondest, most honest and memorable I have ever had with another person.
We took the boat across Lake Michigan to Michigan City, IN a few times and spent the night. As anyone who has sailed Lake Michigan can tell you, at times, it can be as daunting as any ocean. One particular trip, a sudden, vicious storm hit while we were in the middle of the lake. We got tossed around, had our sails torn, nearly snapped our mast, and came close to being swamped by waves or capsized numerous times. That experience bonded us like no other. We eventually limped into the harbor in MC, smiled at each other and had a couple of beers without saying more than 10 words. I truly trusted Bob with my life and despite having the boat pounded, never lost faith in him as a sailor or a friend. Sometimes, we'd spend the whole day just cleaning the boat, never leaving the mooring (when in Monroe Harbor) or dock at Burnham Harbor, and despite the hard, hot labor, we'd leave exhilarated.
Bob's craft as an artist and mine as a marketing person gave us lots to talk about professionally. Politically, we were pretty much aligned, but we could have highly-spirited discussions without being disagreeable. Bob couldn't have been more thrilled for me when I joined him among the ranks of Porsche owners. It was but one more passion we shared.
When we each started families, mine a couple of years before his, we fell out of touch. I just couldn't justify spending as much time on the boat and away from family. When Hannah came along, Bob and I were having a chat and he admitted how his life would never be the same again, and how deeply he loved being her father. Once again, we shared a passion, the greatest in the world.
Sail on Skipper.