Tobey committed to UVA over schools such as Maryland, Pittsburgh, and Xavier. During his time at Virginia, he split time between being a starter and being one of the first substitutes off the bench. His play off the bench earned him the ACC Sixth Man of the Year award in 2015. Tobey was on the United States national under-19 basketball team that won the 2013 FIBA Under-19 World Championship. Tobey ended his collegiate career as Virginia's all-time leader in games played, appearing in 138 games over his four years.

After going undrafted in the 2016 NBA draft, Tobey joined the Charlotte Hornets for the Orlando Summer League and the Utah Jazz for the Las Vegas Summer League. On July 25, 2016, he signed with the Hornets, but was waived on October 22, 2016 after appearing in two preseason games. On October 31, 2016, he was acquired by the Greensboro Swarm of the NBA Development League as an affiliate player of the Hornets. On February 3, 2017, he returned to the Hornets on a 10-day contract. On February 13, 2017, he signed a second 10-day contract with Charlotte, despite having not appeared in a game during his first 10-day contract. He made his NBA debut two days later, recording two points and three rebounds in 11 minutes off the bench in a 90–85 loss to the Toronto Raptors. On February 24, 2017, after the second 10-day contract expired, Tobey returned to the Swarm.

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