Losing a Brother: Mark Winkler. Charlie Kaplan and Brother Jay

Jay, Charlie and Mark

Losing a Brother – A Life Cut Short,  A Lesson That Endures

Losing a Brother like Jay is something I’ll never fully comprehend. He was the picture of health — vibrant, energetic, and always on the move. He never smoked, drank, did drugs, or showed signs of illness. And yet, at just 44, Jay was taken from us by bladder cancer.

Losing a Brother so suddenly and unexpectedly left a hole that will never be filled. But his spirit lives on in my memory, and in the way I now approach life. Because of Jay — his passion, his purity, and his untimely death — I do my best to live each moment fully, never taking a single breath for granted.

A Rebel

Losing a Brother: Work like you don;t need the money, love like youve never been hurt, dance like no one is watching Jay Winkler signature

Jay was a barefoot enthusiast who hated wearing shoes. He made sure to sign every email with the motto you see above. We incorporated a snippet of it, and his love of bare feet, into the design of his tombstone.

In 1999 Jay was interviewed on CBC Radio about being a barefoot enthusiast. When you click below to listen to that interview, you’ll see that Jay was a very funny man!

Losing a Brother: Gravestone of Mark Winkler's brother Jay

Barefoot and Timeless: Jay’s Spirit Returns…

 

On Father’s Day, I gave my niece Rita a gift unlike anything she could have imagined. Using generative AI, I recreated the essence of her late father, Jay, who passed away 23 years ago from bladder cancer. Now, I know this kind of technology can raise eyebrows—some might call it eerie or unsettling—but let me be clear: Rita was deeply moved. She loved it.

This wasn’t about tech gimmicks or digital tricks. It was about something far more human: giving Rita a chance to feel her father’s pride, to hear the love he would have spoken had he been here to witness her incredible journey as an artist and a woman. That moment—that connection—was real.

No, AI isn’t flawless. And my execution wasn’t either. But that was never the point. What matters is that, for the first time in decades, Rita heard what only her father could say. And while AI can never replace memory or human presence, it can, when used with care, become a bridge. A bridge to love, to healing, to something once thought impossible. That’s what made this gift unforgettable. And why I know it will live in her heart forever.

P.S. For those of you who knew Jay, you might remember his quirky love for going barefoot—he was a true barefoot enthusiast. The video ends with a quote that perfectly captures his spirit. In fact, it was his signature on every email he ever sent: a simple line that said everything about the way he chose to live.

 

Losing a Brother: Mark Winkler's brother Jay with wife Helen and their 3 daughters

Jay, Helen and their three daughters

Losing a Brother:

Jay and cousin Louis