A Stepping Legend Who Will Always Be With Us. Ty Skippy

On the weekend videos, photos, memories, and comments on social media expressed condolences and recalled countless dance memories. One of the greatest steppers of all time passed away on December 26. Rest in Peace Stepping Legend, Ty Skippy.

Tyrone “Ty Skippy” Winfield was from the Wild 100’s on the far Southside of Chicago from the West Pullman area. The Wild 100’s was the Roseland neighborhood located along and south of 100^th street where racial conflict, gangs, drugs, extreme violence, and crime were rampant by the 1980s and still today. Roseland is 17 miles from downtown Chicago, but life there is a constant war with extreme violence and brutality against humanity on a regular basis. Amidst these harsh realities, Ty Skippy, like many young men and women from the Wild 100s, grew up there and was still stepping.

The Legend of the Coldest Feet on the Wood

For more than forty-five years, Ty Skippy was consistently one of the coldest steppers of his time. He has been a legend for years. His greatness on the dance floor spanned across decades of dancing at places like the Beverly House or East of The Ryan. Sometimes steppers saw him at The Dungeon burning a hole in the floor with other greats like Dirk, Darrel Davis, Black Fred Astaire, Lil Mike, Womack, Big Henry, Derek Nute, and Pretty Ricky – to name a few. Ty Skippy was winning contests then, in the middle of his life, and even now, outlasting many of the steppers that started with him in his era. He was hard to beat and was an undisputed champion of Stepping.

“If anyone should be called the G.O.A.T. it is Ty Skippy.”

– Anonymous

He is recognized as the epitome of Old School. When Ty Skippy and his wife, Celeste danced, it was Original Old School through and through. Over the years, Ty Skippy upgraded his dance adding some new school spins and turns but he stayed true to Old School roots. Some say he was more Freestyle. Regardless, he was still getting better. At the center of Ty Skippy’s Stepping legacy is the dance imprint he left in the stepping community. Steppers learned from watching his greatness and talent across decades and added to their dance from what they saw Ty Skippy do. No doubt, a part of him lives in our dance already. Steppers inside and outside of Chicago showcase pieces of Ty Skippy in different ways at every set and on the contest stage.

Why Ty Skippy Is Remembered As A Stepping Legend

Ty Skippy was not too Legendary to Learn

Ty Skippy watched and participated to learn from other steppers and even younger steppers. Have you seen the video of Tyk Man teaching Ty Skippy how to do a new turn? He wasn’t shy to be a student. Whether man-on-man or in the middle of “The Get Down” he not only danced but Ty Skippy watched what others were doing. He was a great model for any stepper to understand that in stepping there is always something new to learn even after dancing for forty-plus years.

Ty Skippy Taught Steppers What He Loved About Stepping

Ty Skippy and Celeste were two of the few instructors left still teaching Original Old School Stepping today. The first time I danced with Ty Skippy was at a convention in downtown Chicago about five years ago. I was just hoping to keep up. I promise you that after those dances, I was happy as a lark because I kept up with him. He did Ty Skippy unapologetically and I was right there staying with him doing my 8-count. This year, I had the opportunity to have a private with Ty Skippy and I am glad because he taught me the six-count and gave me a real hands-on taste of Original Old School.

Ty Skippy Chose Living through the Dance

When I look at Ty Skippy, I see Chicago. Whether it was the toothpick in his mouth, the finger waves in his hair, the way that he and Celeste always showed up in coordinated fashion on the set, the freestyle in his dance, or his rapid footwork known as “the fastest feet in the land”, to me he represented “Chicago.” He loved Stepping and was a trendsetter for the dance. Sometimes when he spoke, Ty Skippy was a rebellious man but made people laugh at the same time. He was Chicago and every part of it. As steppers, we think about keeping Stepping alive. On the contrary, Stepping has kept us and many steppers like Ty Skippy alive against all the odds. Every time I saw him on the set, I knew he chose to live in this dance instead of dying on the streets. The more he showed up, the more he chose to live. His body is gone physically, but his spirit in this dance will last forever on the set.

Ty Skippy in 2021

In 2021, I loved the Winfields’ transparency on social media about their love for each other and Stepping. On February 6, 2021, Ty Skippy and Celeste got married. They sealed it with an unforgettable kiss while dancing on Facebook live. In September, his niece, Henrietta Winfield, placed first in the WLSC New School category with Barack Swanigan. When Ty Skippy scooted around me to get close to the stage to watch the performance at the contest, he was claiming the best seat in the house for this moment.

He must have been proud when Henrietta won first place “again” in the New School category at WLSC. Henrietta’s first WLSC New School first-place win was in 2018 with her uncle, Ty Skippy. When something someone loves so much becomes a family tradition that their younger generations can love as much and win doing it, this moreover, is what makes Ty Skippy a legend with a “living family legacy.”

These are only some of the reasons that Steppers will not forget him. Rest in Heaven Ty Skippy.

“I miss him, and I love him. Tyrone did it his way. He lived a rich life with no boundaries, and he was well-loved by many.”

-Celeste Winfield