Sherwin Ernst

Sherwin J. Ernst, 92, aka The Wicker Park Kid:

Sherwin J. Ernst, passed away peacefully at the age of 92, leaving behind a legacy marked by adventure, devotion, strength, and wisdom. Sherwin lived a life that spanned continents, careers, and countless personal transformations. Though his journey was long and rich, it feels all too brief to those who loved him.

Born in Chicago in 1932, Sherwin lived in the Wicker Park neighborhood surrounded by his close-knit family of uncles, aunts and cousins. He moved to Louisville, Kentucky when he was 6 and would eventually play football there for Male High School but always found time to visit his extended family back in Chicago. After graduation Sherwin took up flying lessons which for a time became his great passion. His early years in those towns shaped the man he would become—one of character, resilience, and a love for life’s experiences. 

 As a young man in the 1950s, Sherwin served in the U.S. Air Force, in time volunteering for air traffic control in Paris where he also enjoyed many a night out as the suave debonair American about town. 

 In 1957 Sherwin returned to Chicago, where he met and fell in love with his wife Sandy and settled into a new chapter as a devoted husband, father and savvy businessman. After a couple retail sales jobs, Sherwin started his own automobile insurance agency and motor club, American Automobile Insurance Brokers. In the beginning he would go out early in the morning, sometimes in the snow, looking for people working on their broken down cars on the road and sell them policies on the spot. Over time he hired salesmen and grew his office staff to over 30 people, becoming the largest independent insurance agency in the Chicagoland area and the first to advertise on television. His memorable commercials—often featuring dramatic footage of old time automobile crashes—made his company a recognizable name to many Chicagoans. 

In the 1980s, Sherwin and Sandy moved the family to Tampa, Florida, where they both transitioned into the world of real estate. Together, they created new opportunities, navigating challenges and embracing the entrepreneurial spirit that had always driven him. Sherwin was always the brains behind the marketing of the family real estate business, still coming up with fresh ideas for their website all the way to the end at age 92.

Sherwin was a man of few words but an abundance of wisdom. He possessed a quiet strength and a sharp sense of humor with a belly laugh that endeared him to everyone he met. 

 Sherwin was a master writer—crafting songs, speeches and stories that captured the essence of his life experiences and the lessons he had learned along the way. His family couldn’t wait to hear the speeches he would give at milestone celebrations knowing they would be both spiritual and personal, filled with humor and insight. 

 In his later years, Sherwin wrote and published his memoir, The Wicker Park Kid, a book that captivated readers with remarkable stories of his adoption, family, personal challenges, spiritual growth, and redemption. His words resonated deeply with those who knew him, offering a glimpse into the complex, multi-faceted man he was.

Sherwin’s later years were also marked by a characteristic shift in appearance, most notably the white beard he grew and his ever-present newsboy cap—symbols of a man who had lived fully, and who wore his wisdom and experience with quiet pride. Despite the passage of time, he never lost the twinkle in his eye, nor his ability to make those around him smile.

As a spiritual guide, Sherwin often spoke of his deep connection to the world beyond, and in one of his most poignant moments, he shared the following words at his mother’s gravesite, which now resonate as a fitting tribute to his own journey:

“Shaul Yosef, Nathaniel Safran, Sherwin Ernst, The Wicker Park Kid…May the messenger of God guide your soul safely through the inner worlds…and may you once again experience and become a part of the essence of those you loved so dearly. May you enjoy the blessings of heaven for all eternity and may God accept you for all eternity…and never shall you return to this world of human suffering. Amen.”

Sherwin’s life, in all its forms and phases, was a testament to the power of reinvention, perseverance, and love. His family, friends, and all who knew him will carry his memory with gratitude and admiration.

Sherwin is preceded in death by his wife, Sandy, and survived by his children Matthew (Stacey), Lynda (Michael) and Jon, granddaughter Hannah, and a wide circle of friends and loved ones. His presence in our lives will be deeply missed, but his spirit will continue to guide us in the stories we share and the lessons he imparted.

May he rest in peace, and may the blessings of heaven be his for eternity.