The Winning Ways of Sissy Winn Inside and Outside the Arena

As Sissy Winn looks to add a Canadian Finals Rodeo and third consecutive NFR qualification to her resume, she gives rodeo fans an inside look at life on the road through the lens of TikTok.

Ashley Castleberry (fourth in world standings); Emily Beisel (ninth in world standings); Jimmie Smith; Sissy Winn (13th in world standings); Jakie Ganter /

Sissy Winn's outgoing demeanor masks her methodical planning and preparation. Sissy's ability to balance her positive, upbeat personality while still being an elite competitor makes her more approachable than the majority of her peers.

Sissy makes her presence inside the arena known by consistently putting herself on top of the leaderboard. Sissy disrupts the norm and makes herself visible outside the rodeo area via social media—especially on TikTok.

Winn's TikTok might appear insignificant until one actually looks at what she creates. She consistently answers questions and shows a behind-the-scenes perspective of life on the rodeo road. The Chapman Ranch, Texas cowgirl gives invaluable information to up-and-comers on how one can make rodeo sustainable/affordable.

Winn says, "One of [her] favorite things about TikTok is showing others that your goals and dreams aren’t out of reach. We all struggle, we all go through things, and [she] like[s] to show that aspect on [her] TikTok." Sissy emphasizes showing both the good and bad times to her followers.

"Your goals and dreams aren't out of reach."

- Sissy Winn

The talented barrel racer's vulnerability online explains why so many fans cheer for her. Winn gives rodeo fans enough of a reason to back her on colorful outfits alone. Sissy, however, connects with these fans beyond a superficial level by showing up for them online. Her content balances between practical advice and funny rodeo stories, such as running at Pendleton with toilet paper trailing out of her boot.

Sissy's approach to rodeo veers from the status quo. She does not have young horses coming up through the ranks nor does she train outside horses for public. This limits her overhead expenses by only paying for her rodeo horses (and minis) and their maintenance. Sissy also admits that she sells horses, because those funds help her to buy the next horse.

Winn began rodeoing seven years ago. In 2021, she finished the year ranked at number 20 in the world standings. She qualified for the NFR the next year in 2022.

When asked about the biggest contributing factor to making the finals for the first time; Winn admits that qualifications to the limited entry "building" rodeos from her 2021 efforts allowed her to capitalize in 2022.

Sissy qualified for the NFR again in 2023, and she looks strong for her third consecutive qualification in 2024 as she sits No. 13 in the barrel racing world standings with $46,790.36 won.

Winn changes her summer route year-to-year. She says that the primary objective is always getting to Vegas. The route to attain said goal varies based on that present year's circumstances. This year, Sissy finds herself in Canada. Winn traded Texas heat and bad ground for Canada's cool temperatures and rainy/muddy conditions. Winn says she wants to qualify for the Canadian Finals Rodeo as well.

Preparing for the summer run is nothing short of preparing for battle. Rodeo athletes experience heightened versions of both winning streaks and dry spells in the summer purely from the frequency of rodeos. Athlete's ability to take each run in stride plays a disproportionate role to their success at the end of the year.

Winn says she mentally prepares for the challenging times by having the perspective that the ups and downs are a part of the process. She avoids the pitfalls of a negative headspace by trusting that bad times always turn around.

The cowgirl does not wear a good buckle - yet.

Her impact on the sport of barrel racing already surpasses what any additional NFR qualification or World Champion title might have. She brings something to rodeo fans that her peers lack: accessibility. She shares the ups and downs. She shares information on how to logistically make rodeo work without going broke in the process. Because Sissy shares, people feel connected.

This athlete-fan connection within the realm of rodeo is rare, because cowboys and cowgirls fail to utilize the tools (social media) at their disposal. Fans cheer loud for Sissy Winn, because she wins, but more importantly—for what she shares.