Leonard "Lenny" Cholewinski Obituary

Leonard "Lenny" Adam Cholewinski,60, born on May 18, 1964, in Elyria, Ohio, passed away peacefully on December 19, 2024, in Greenwood, Indiana, surrounded by his beloved family. Lenny was a dedicated IT professional who spent many years contributing his expertise to Sony, where he left a lasting impact through his work and camaraderie with colleagues.

He was a proud graduate of Franklin Central High School, Class of 1982. Lenny furthered his education by earning a Bachelor's degree in Aviation from Indiana State University, followed by a degree in IT from Ivy Tech Community College. His thirst for knowledge and passion for aviation truly defined his professional and personal journey. He also honorably served in the United States Air Force, earning the rank of Staff Sergeant, demonstrating his commitment to his country.

Lenny’s personality shone brightly in all that he did. Known as a jokester with a happy and positive disposition, he possessed a strong will and an unwavering love for his family. He held a deep appreciation for the people in his life, never meeting a stranger. His political interests often sparked engaging conversations, as his humor and warmth drew others to him.

His diverse hobbies included a love for music, old cars, and motorcycles. Lenny was a true outdoorsman, relishing camping trips and architectural designs. He was particularly proud of his skills as a pilot and even took joy in riding a unicycle while balancing passengers on his shoulders—these unique talents brought laughter and pride to his family, who cherished every memory made together. Leonard loved the weather and researching the weather, he made sure all his family and friends knew what the weather forecast would be each day along with his predictions, he was known to everyone as the Weatherman.

Lenny is survived by his devoted wife of 16 years, Phyllis Kay (Shepherd) Cholewinski, and his loving children: Alexander Adam (Emily) Cholewinski, Bailey Renea (Tyler) Cox, and Dawn Davis with her fiancé Jay. His legacy will continue through his grandchildren, Madeleine and Anderson, who brought him immense joy. He is also survived by his father, H.A. (Angie) Cholewinski, and his mother, Connie (Robert) (Karr) Higgens, along with his siblings: Charlene (Joe) Humphrey, Breanna (Rob) Kinkopf, B.J. "Whop" Cholewinski, Scott (Deanna) Stanchak, Vicky (Steve) Lester, Sherri Schacht, and April Gray. Lenny leaves behind several nieces and nephews, all of whom will remember him fondly.

The family will gather to honor Lenny's life during visitation at Newcomer Funeral Home in Indianapolis on Saturday January 4, 2025, from 11:00 AM to 1:00 PM, followed by a funeral service with military honors at 1:00 PM until 2:00 PM at the same location.

In lieu of flowers, donations may be made to Lenny's grandchildren. Donation envelopes will be available at the service. Please contact the funeral home with any questions. 

Lenny's indelible spirit and loving heart will forever live on, in the memories of those he touched.