Cannady was introduced to basketball by his father, a former college player, who showed him tapes of Michael Jordan. He grew up playing Amateur Athletic Union basketball for MBA Select. Cannady played for Marian High School in Mishawaka, Indiana. As a junior, he averaged 21.9 points, 4.8 rebounds, 3.3 assists, and 2.9 steals per game. After the season, Cannady joined Spiece Indy Heat at the Nike Elite Youth Basketball League, leading his team to the EYBL Finals at the Peach Jam. He finished high school as the winningest player in Marian history and ranked second in career points, with 1,475. He also played the quarterback position on Marian's football team for four years and was a two-time all-state selection. Cannady was considered a three-star basketball recruit by 247Sports and Rivals and committed to play college basketball for Princeton over several other NCAA Division I offers.
College career
Cannady averaged 11.6 points and 2.5 rebounds per game as a freshman, helping the team reach the NIT. During his sophomore season, Cannady helped Princeton go undefeated in Ivy League play, win the inaugural Ivy League basketball tournament, and participate in the 2017 NCAA tournament. He averaged 13.4 points, 3.6 rebounds and 1.9 assists per game, earning Honorable Mention All-Ivy League honors. On February 16, 2018, Cannady scored a career-high 32 points in a 107-101 triple overtime loss to Cornell. As a junior, Cannady averaged 16.7 points and 5.4 rebounds per game on a team that finished 13-16. He was named to the Second Team All-Ivy League. On January 18, 2019, Cannady entered a Wawa store under the influence of marijuana and began arguing with customers, eventually punching a campus patrolman. He was arrested, but his aggravated assault charge was downgraded to a disorderly persons offense and he was sentenced to community service. Cannady was suspended from Princeton and began seeing a therapist to manage anxiety. He reinstated by the team on February 8 against Yale and played four games before announcing on March 1 that he was ending his season due to a personal matter. In 16 games, he averaged 18.2 points, 5.8 rebounds and 1.7 assists per game during his senior season. Cannady finished his career with 1,515, the fifth highest in Princeton history.
Professional career
After going undrafted in the 2019 NBA draft, Cannady joined the Oklahoma City Thunder at 2019 NBA Summer League. On October 15, 2019, he signed with the Brooklyn Nets of the NBA, four days before being waived by the team prior to the regular season. On October 27, Cannady was allocated to Brooklyn's NBA G League affiliate, the Long Island Nets. During Cannady's rookie season, he had to balance playing professional basketball with completing his sociology degree from Princeton. On December 27, he scored a career-high 33 points along with eight rebounds and three assists in a 109–95 win over the Erie BayHawks. Through 40 games with Long Island in the 2019–20 season, Cannady averaged 14.4 points, 3.9 rebounds and 2.6 assists per game.
Personal life
Cannady's father, Tony, played college basketball for Bethel College.
