James Orbie “Jimmy” Penicaro, 42, of Winamac, passed away Sunday, March 22, 2026.
He was born on August 11, 1983 in Plymouth, IN to Timothy Joseph and Brenda Carol (McCullough) Penicaro. He was an outgoing and fun-loving kid who enjoyed playing sports. Jimmy was a lifelong Chicago Bears fan.
He attended Winamac High School. He worked hard throughout adulthood and was a talented mechanic. He enjoyed cooking in the kitchen and on the grill. Despite the challenges he faced in life, he loved his family fiercely.
Survivors include:
Alysa Penicaro, Daughter
Carmela Penicaro, Daughter
Brenda Carol and Greg Henry, Parents
Angela (husband: Jason) Hale, Sister
Deanna (husband: Donald) Gradowski, Sister
Melinda Penicaro, Sister
Shawn (wife: Kelly) Penicaro, Brother
Gavun Henry, Brother
Many Nieces and Nephews
Danny (wife: Ellen) Penicaro, Uncle
Penni Hilton, Aunt
Cathy Penicaro, Aunt
Charlie Louthen, Uncle
Rana (husband: Alvin) Parish, Aunt
Raymond (wife: Dulscenia) Henry, Uncle
Marvin Henry, Uncle
Numerous Cousins
Preceded in death by:
Timothy Joseph Penicaro, Father
Frank and Arnabelle Mary (Stepp) Penicaro, Grandparents
Orbie and Christine (Finley) McCullough, Grandparents
Stanley Keith and Lois Charlotte (Zellers) Henry, Grandparents
James Arnold Penicaro, Uncle
Bradley Allen Penicaro, Uncle
Tina Marie (Penicaro) Kasten, Aunt
Charlotte Ann McCullough, Infant Aunt
Eddie Guy McCullough, Uncle
Linda (McCullough) Louthen, Aunt
Porter Rodger McCullough, Uncle
Floyd Hilton, Uncle
Carol Henry, Aunt
David F. Penicaro, Cousin
David Louthen, Infant Cousin
Cremation will take place at Frain Crematory in Winamac, IN.
The family will Host a Celebration of Life at a later date.
In lieu of flowers, memorial contributions may be made to the family for Jimmy’s daughters' education.
Donations may be mailed to:
Frain Mortuary
c/o Brenda Henry
PO Box 248
Winamac, IN 46996.
Online tributes may be offered at www.frainmortuary.com.
