Cover photo for Mr. James Jason Winkler's Obituary
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Mr. James Jason Winkler

February 15, 1980 — November 30, 2023

James Jason Winkler, 43, passed away on November 30th, 2023, in Wesley Chapel, FL.

James’ family is devastated and shocked by this sudden passing, James had just moved to Florida and was looking forward to getting married in April to his Fiancé Didamia Santiago, his first born daughter Jacquelyn’s wedding in August,his youngest child Brandon graduating from high school in the Spring and becoming a godfather to his first born nephew Logan.

James was born on February 15th, 1980, to James and Victoria Winkler in Brooklyn, NY. He grew up with his siblings, John Winkler, Jason Winkler, and Jennifer Winkler in Queens, NY.

As a child, James’ favorite tv shows were He-man, and transformers. He loved listening to all types of music, and watching sports. He was a very bright and inquisitive child and excelled in just about everything he did. His father was the coach of many of his baseball and football teams growing up. James also served as an altar boy for several years at St. Brigid’s Church in Brooklyn, NY.

In high school, James was a great athlete and very talented. He played basketball and baseball, and was able to pitch in Yankee Stadium during his High School career. He was also well known in the football and softball communities all around Queens, NY. James was a leader on and off the field and his teammates called him captain. His favorite sports teams were The Atlanta Braves, Dallas Cowboys, and the New York Knicks.

In 1999, James Winkler and now ex-wife Michele Lopez had their first child Jacquelyn and went on to have Alyssa and Brandon. James was immensely proud of his children and his nephew and future godson, Logan.

James moved to Wesley Chapel, FL in June of this year with his Fiancé Didamia and their dog Maxx. He loved moving to Florida and starting a new chapter of his life. James enjoyed taking rides with Maxx and having him as his co pilot. He looked forward to buying a house and settling down in the Sunshine State.

James is predeceased by his brother Brian Winkler, uncles Richard Viohl, Richard Schwerdt, Robert Schwerdt, and uncle/god father Kenneth Winkler. James is survived by his parents, Victoria and James Winkler, fiancé Didamia Santiago, siblings John Winkler, Jason Winkler, Jennifer Winkler and nephew Logan Winkler, children Jacquelyn Winkler, Alyssa Winkler, and Brandon Winkler.

Relatives and friends may visit with the Winkler family on Friday, December 8, 2023, from 6:00pm- 8:00pm at Casey's Eastside Memorial Funeral Home and Cremation Care, 1987 East Main Street Waterbury, CT. Burial will be held privately at the convenience of the family. Loving kindness is always welcome, and it only takes a moment to offer a message of condolence, words of comfort, or share a memory with the family and friends of someone important to you. Please visit the funeral home’s tribute page at to do so.
To order memorial trees or send flowers to the family in memory of Mr. James Jason Winkler, please visit our flower store.

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Friday, December 8, 2023

6:00 - 8:00 pm (Eastern time)

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Casey's Eastside Memorial Funeral Home & Cremation Care

1987 East Main Street
Waterbury, CT 06705

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