A prominent collegiate baseball player known for his powerful left-handed bat. Born on September 5, 2001, in Belleville, Illinois, he attended Edwardsville High School, where he was a highly-rated prospect, earning All-Southwestern Conference First Team honors multiple times and being named to the Illinois High School Baseball Coaches Association All-State Team. He was also recognized as one of the top first basemen nationally by Perfect Game.

Westcott began his college career at the University of Louisville, playing in 12 games in his first season on the field in 2022. He later transferred to the University of Illinois at Urbana-Champaign, where he has become a key offensive force for the Fighting Illini.

At Illinois, Westcott has consistently been among the top power hitters in the Big Ten Conference. As of the end of the 2025 season, he finished his Illini career ranking second all-time in program history with 43 career home runs. He earned All-Big Ten Third Team honors in 2024 and was named to the Big Ten All-Tournament Team in 2025. He's also been recognized for his academic achievements as an Academic All-Big Ten selection.

Off the field, Drake is passionate about cancer awareness, participating in and organizing home run derby events to raise funds for childhood cancer awareness and St. Louis Cardinal Glennon Children's Hospital.