Jerry Steven Pearlstein

He was born in Chicago, Illinois, growing up in the Albany Park neighborhood and graduating from Roosevelt High School. He earned a Bachelor of Arts at Northern Illinois University. He also earned the moniker “JP” there while running a campaign for campus office for his lifelong friend Marvin Leavitt.

He served in the U.S. Air Force and trained as a medic.

A make-it-happen spirit and desire to help were the hallmarks of JP’s life. He was active in establishing a family business, Mid-Continental Uniforms, when he was still in high school. When he was 25 his dad died, and he managed the sale of the business in a manner that would support his mother whom he lovingly cared for to the end of her life. He partnered with friend Michael Davis to found the Alternative Telephone Company. In 2002, he and his wife, Rebecca Bloomfield, began to help people who had no employer-based health insurance. Jerry Pearlstein & Associates Ltd serves hundreds of clients by keeping up with the information needed to get the most benefit from the ever-changing health insurance landscape. They have won multiple Awards of Excellence.

In 2022 he moved with the wife he called, “the best thing that ever happened to me”, to Sun City Anthem in Henderson, Nevada. It was a life he had always dreamed of—no winter cold, lots of good food, good entertainment and good friends. In 2023 he played in the Senior World Series of Poker and came in the money. Unfortunately, his dream of being the first person to win both the Senior and regular World Series of Poker was denied him due to ill health.

Rebecca survives him as well as two daughters from a previous marriage, G(J) Pearlstein and Ellyn Pearlstein.

Contributions in his memory can be made to Wounded Warriors, St. Jude Children’s Research Hospital and Shriners Children’s Hospital.