In Lucky for Winnie, Winnie finally gets the opportunity to gentle her own horse. While she hopes it will be the beautiful Arabian, she instead gets stuck with Lucky, a headstrong Mustang. Meanwhile, Winnie feels tempted to submit a traced drawing for the school art fair because she doubts her artistic skills. Winnie learns that the love and support of her family is better than being a good artist. Plus, when she pushes past her first impression and shows Lucky that she loves her no matter what, their bond grows.