Wigginton was born March 28, 1998 in Halifax, Nova Scotia. He played one season of basketball at Prince Andrew High School in Dartmouth, Nova Scotia. After that, he went down to the United States to join Oak Hill Academy in Mouth of Wilson, Virginia. During his time there, he earned a four-star recruit ranking by ESPN. Before starting his collegiate career at Iowa State, he played 22 minutes for the World Select Team at the 2017 Nike Hoop Summit. He scored 11 points and dished seven assists. As a college freshman, he was named to the Big 12 All-Newcomer Team with averages of 16.7 points, 3.7 rebounds and 2.8 assists in 33.0 minutes. One year later, he was given the Big 12 Sixth Man Award. Wigginton averaged 13.5 points, 4.0 rebounds and 2.1 assists. He went unselected in the 2019 NBA Draft. He joined the Raptors for Summer League before signing his first professional contract with the Timberwolves.