Wanamaker was born in Philadelphia on July 25, 1989 to Brad Wanamaker, Sr. and Deborah Samuel. He has four siblings: James, Crystal, Latisha, and twin brother Brad, who he was born 71 minutes after. Wanamaker grew up frequently playing basketball with his father and twin brother at local North Philadelphia playgrounds. He played basketball under head coach Dennis Seddon at Roman Catholic High School in Philadelphia, where was teammates with both Brad and coveted recruit Maalik Wayns. In his senior season, he averaged 14 points per game and led the team to a 28–3 record and a Catholic League title. He also earned second-team all-league and all-city honors. In the 2007 recruiting class, Wanamaker was rated a three-star recruit by 247Sports.com. He had received a scholarship offer to Georgetown as a junior with his brother but his recruitment was hindered by an injury.
On November 3, 2011, Wanamaker was selected by the Fort Wayne Mad Ants with the tenth pick in the seventh round of the 2011 NBA Development League Draft. About two weeks later, the team waived him. In 2012, Wanamaker took part the Eurobasket Summer League in Las Vegas, where he played for Union Monaco. After five games in the exposure camp, he averaged 6.6 points, 3.6 rebounds, and 2.2 assists per game. In the following summer, he competed in the WorldwideSM Invitational camp at the University of Nevada, Las Vegas. Later that year, Wanamaker played for s.Oliver Baskets of the Basketball Bundesliga for the preseason. In 2014, he returned to the ESL and competed in Brooklyn for Team Buenos Aires and in Las Vegas for Team Monaco. In Brooklyn, he was named league MVP. For the 2014–15 season, Wanamaker signed with TSV Tröster Breitengüßbach of the Regionalliga, the fourth-best basketball league in Germany. In two games, he averaged 19.5 points, 4.0 rebounds, 5.0 assists, and 2.5 steals per game. Wanamaker completed the season with the Regionalliga team BC Erfurt, averaging 25.9 points, 7.3 rebounds, 3.2 assists, and 2.9 steals. He remained with Erfurt for the following season and was averaging 20.8 points, 7.6 rebounds, 4.0 assists, and 3.4 steals after 17 games. In 2016, Wanamaker moved to Lithuania to play for BC Šilutė of the National Basketball League, the second-best league in the country. In 44 games, he averaged 13.3 points, 5.3 rebounds, 4.3 assists, and 2.3 steals per game. For 2017–18, Wanamaker joined BC Vytis in the NKL. On December 12, 2017, he was named NKL Player of the Week by Eurobasket.com after helping defeat Šilutė with 25 points, four rebounds, and six assists.
Personal life
Wanamaker is the twin brother of Boston Celtics basketball player and former Pittsburgh college player Brad Wanamaker.