Sherman Bay Chickering
November 4, 1940 – February 22, 2023

He was known alternatively as Sherm or Chick, and left us in February ’23, in Madison WI. He was born in Honolulu. His father, William Henry Chickering, was in the class of ’37. His mother was Audrey Hammond Bay. After Choate, he roomed in Timothy Dwight with Kirk MacDonald and Lew Spratlan. He was on the Freshman Prom Committee and Freshman squash team, and was a member of Zeta Psi. Chick had a beautiful lyric baritone voice, displayed in the University Quartet with Peters Clark and Sipple and Dixie Carroll. He sang in the Yale Glee Club, the Battell Chapel choir, and the Yale Glee Club. He was an excellent guitar player and folk singer, writing much of his own material. I remember as if it were yesterday, his wonderful “Vermilion Hair” (“I’m a sawed-off punk, kinda shrunk, but what do I care, with her vermilion, vermilion hair…”)

His last year at Yale he created a magazine called Moderator, whose raison d’être was to assemble and organize students’ beliefs and opinions around the country and eventually the world. He pursued this goal for a few years, but was not successful in finding financial backing. He offered Kirk MacDonald, the editor of our 25th reunion book an extended philosophical piece which was not used. A sample of his rather good writing can be found at here.

From Kirk: “Sadly, time passes sometimes without completion of relationships. Chick was one of the most talented men I’ve ever met. Seeing him squander that talent and effectively go over the edge without a return of any sort left me with a great void.

“He contributed an incredibly long essay to the 25th book, which I edited and sat in a meeting where we all decided not to publish his tell-all story. Tried to remain in contact, but he staunchly refused. Biggie kept pleading with me to send out the rescue dogs for contact.

“These are the times when we gather our belongings and pack up for the next trip. Not advisable to take baggage which will not serve nor to regret the things and people we have passed along that way. Better to forget and forgive than to fret and relive.”

P.S. Here is a addition to Chick’s obituary, sent by his brother William. Sherm, Chick to his friends, had an unusual and fascinating life.

William Chickering wrote: “Born in a near-mythic Hawaii before World War II and at age four losing his father to that war, Sherman had a sense of predestination all his life, which sustained him through two hellish boarding schools before arriving at Yale, where his intellectual brilliance and musical talents brought recognition and friendship. It then propelled him to start a national magazine for student leaders, called Moderator, a concept doomed by growing anti-elitism in the early Sixties. Betting and losing everything on the magazine, his response was to embrace that anti-elitism and its larger counterculture. This brought him to the San Francisco Bay Area, where he founded Common Ground, a newspaper delivered weekly to stores with a counterculture clientele. The idea of a free newspaper surviving on ads aimed at a specific demographic was revolutionary, and Common Ground was arguably the first of its now-myriad kind. Then, like many people in that time and place, he sank away into the alternative culture — but not before selling his interest in the paper for a tidy sum (enabling him, later in life, to look back with pride at always having made his living with his pen, always self-employed). When he came up for air, in Madison WI, he described having hit bottom then bounced along it for several years, during which he benefited at times from the kindness of food banks and St. Vincent de Paul. His sense of predestination turned to belief that he could read his fate in the stars. Despite this otherworldliness, he retained a delightful capacity for self-mockery, sometimes signing his name with a J.D. after it – for “Journey Downward.” He also took on what looked like a minor task – dealing with Oklahoma oilmen about a few inherited mineral rights. Sensing that the land was not as worthless as the landmen claimed, he proceeded to check out a copy of Oil and Gas Law from the Madison Public Library, memorize it, then outwit them all, eventually making a great deal of money for himself and other inheritors. From this he routinely donated to St Vinnie’s and other charities, eventually giving away hundreds of thousands of dollars. His final act was to predict his death from the concatenation of Pluto and Mars and to die in his sleep on February 22nd of this year, roughly on schedule, proud also that he had never needed medical insurance, medicine, or medical care.

“He leaves behind one brother, William, a beloved sister-in-law Bénédicte, and a niece and nephew, Alma and Sacha – all beneficiaries of his final, triumphant 3rd Act.”