Winthrop ran a jelly bean guessing booth at the town fiesta, offering guesses as to the number of jelly beans in a jar for a nickel a guess. He waited the entire day for Abigail's guess, which was wrong, but made her the winner of the jelly beans as the only guesser for the day. While waiting for her guess, he missed his infant son's first words ("Where's Daddy?").
The year before Lucky relocated to Miradero, Winthrop injured his back when he tripped on jelly beans. When he threw his back out again putting up a sign advertising ice cream, Winthrop permitted Lucky, who was still 12 years old at the time, to run the store for a week until he could recover. At the end of her term, Lucky gave Winthrop a hug, fixing his back.
Winthrop did not employ Lucky the following summer.
Behind the scenes
Winthrop is voiced by Dee Bradley Baker.