Cover photo for James "Jay" Henderson Cherry IV's Obituary
James "Jay" Henderson Cherry IV Profile Photo

James "Jay" Henderson Cherry IV

October 24, 1968 — October 18, 2022


James "Jay" Henderson Cherry IV


James “Jay” Henderson Cherry IV, 53, of Bloomington, passed away on Tuesday, October 18, 2022, at his home.


He was born on October 24, 1968, in Schenectady, New York, the son of James Henderson III and Merrie “Jo” (Cranford) Cherry.


Jay is survived by his mother of Shelbyville; son, Jason Cherry of Chicago; daughter, Caroline Cherry of Bloomington, sister, Merrie Anna Cherry-Cross of Lexington, South Carolina; brother, Jonathan Cherry of Shelbyville; former wife and mother of his children, Shelly Caplinger of Nashville; nephews, David Cross and Ian Cross; and niece, Lydia Cross.


He was preceded in death by his father.


Jay graduated in 1986 from Shelbyville High School. He continued his education at the University of Evansville, obtaining a Bachelor of Science in Mechanical Engineering in 1991, as well as receiving a Master’s in Business Administration from the University of Notre Dame in 1993.


He was the former Owner and President of Wellman Furnaces, Incorporated. His duties included concentrating on the Asian and Southeast Asian markets, with extensive working experience in Japan, China, South Korea, Thailand, Singapore, and Malaysia.


Jay was heavily involved in the First United Methodist Church of Bloomington. He served on staff as the Director of Finance, and additionally volunteered for the Board of Trustees, Stewardship Team, Technology Team, and with the Youth Ministries.


He also served on the Board of Directors for the Evansville Alumni Association.


Jay loved music, whether it be enjoying the church’s music programs, or attending regular concerts with his friends. He also enjoyed cycling, camping, and travel, namely to Thailand, Hawaii, and Oak Island, North Carolina. Jay’s love for his friends and his emphasis on the importance of family was evident in all he did in life.


He also leaves behind his big, white, fluffy dog, Bear “Bearbo”.


Jay’s Visitation will be from 4 PM to 6 PM on Friday, October 28, 2022, at Freeman Family Funeral Homes and Crematory, Carmony-Ewing Chapel, 819 South Harrison Street in Shelbyville.


Friends may gather one-half hour prior to the Funeral Services at 11 AM on Saturday, October 29, 2022, at the First United Methodist Church, 34 West Washington Street, in Shelbyville, with Reverends Colin Cress, Heather Cress, and Lisa Shubert Nowling officiating.


Charitable contributions may be made to the Youth Ministry Fund of the First United Methodist Church of Bloomington at, or can be sent to 219 East 4th Street, Bloomington, IN 47408.


Online condolences may be shared with Jay’s family at


To order memorial trees or send flowers to the family in memory of James "Jay" Henderson Cherry IV, please visit our flower store.

Past Services


Friday, October 28, 2022

4:00 - 6:00 pm (Eastern time)

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.

Funeral Service

Saturday, October 29, 2022

11:00am - 12:00 pm (Eastern time)

First United Methodist Church, Shelbyville, IN

, Shelbyville, IN 46176

Friends may gather one half hour prior to the service

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


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