ROLE IN THE ANIME
Winona is not a main character in the anime series of Pokemon, so I am going to talk about her role in the two episodes that she appears in, Who's Flying Now? and Sky High Gym Battle which are episodes 84 and 85 in Pokemon: The Advanced Generation Series. (You can see more images from these episodes in my gallery section as well).
Winona is considered a "Genius Flying Pokemon Trainer" from the people in her city. This is a huge compliment because Fortree City is a place that has always had respect for the sky and Flying Type Pokemon, so for her to be considered a genius in just that, it's a large compliment from the people. Once a year, Fortree City holds the Feather Carnival, where they celebrate the sky. Winona does her part every year by taking the children, and anyone who wants to fly, up on one of her Pokemon. In the anime she is seen taking children on her Skarmory. She felt like it was important for people to experience the sky in the same way she does during these festivals. The children all love her, and explain that Ash, Brock, May, and Max that she is the Fortree City Gym Leader for her mastered skills and respect she receives.
During the carnival, Team Rocket strikes and attacks all of the Flying Type Pokemon with electric shocks, which is one of their obvious weaknesses. They take all of the injured Pokemon and put them in a container on the back of their new Pokemon-stealing-machine. Winona, seeing a cloud of dust and hearing noise from her Gym, jumps on the back of her Skarmory and rushes to the scene. This shows that Winona isn't afraid of danger when it comes to the safety of Fortree City. It is more important to her that everyone is safe than staying back and ensuring her own safety. This passion for others makes her stand out as a Gym Leader. When she arrives, she watches Ash use Pikachu and his Swellow attack, and be attacked by electricity. After they are both kidnapped, Winona commands Skarmory to use Steel Wing and go right through the machine, blasting Team Rocket off again! The Pokemon were saved all thanks to her and her bravery. Later in the night, she flies in the sky with other Flying Type Pokemon to end the celebrations in a beautiful dance-like performance.