Simon spent his senior season at Brewster Academy in Wolfeboro, New Hampshire, where he blossomed into a consensus top-40 national recruit in the class of 2015.

In leading the team to a 34–1 record, the NEPSAC Class AAA title and the National Prep Championship, Simon averaged 12.5 points, 5.0 rebounds, and 3.5 assists per game.

[2] Simon received over 20 Division I scholarship offers from the likes of Indiana, Kansas, and Louisville, but ended up selecting Arizona.

Simon had a breakout sophomore season, tallying 20 double-digit scoring performances and nine double-doubles in 33 games, all of which he started.

[7] On September 12, 2019, Simon signed an Exhibit 10 contract with the Bulls and was added to the team's training camp roster.

[10] On August 14, 2020, Simon signed a one-year deal with the Illawarra Hawks of the Australian National Basketball League (NBL).

[11] On August 19, 2021, Simon signed a six-week contract with ratiopharm Ulm of the German Basketball Bundesliga (BBL) as an injury replacement for Karim Jallow.

[18] On December 1, 2023, he joined Paris Basketball of the LNB Pro A and EuroCup as an injury replacement for Sebastian Herrera.