Kaleb Canales
In 2005, Canales was hired as a video intern for the Portland Trail Blazers, and was eventually hired as the team's video coordinator. In 2009, he was promoted to an assistant coach for the team. In 2010, Canales served as the Blazers' head coach during the NBA Summer League. He was promoted to interim head coach of the Trail Blazers after head coach Nate McMillan was dismissed on March 15, 2012. Canales became the youngest active head coach in the NBA and the first Mexican-American coach in NBA history.
Jon Gruden
Jon David Gruden (born August 17, 1963) is an American football coach who is the head coach of the Oakland Raiders. He had been the head coach of the Raiders from 1998 to 2001 and Tampa Bay Buccaneers from 2002 to 2008. With the Buccaneers, he won Super Bowl XXXVII in 2003 in his first year with the team, defeating the Raiders, who had traded him to Tampa Bay the previous offseason. At the time, Gruden, aged 39 years, 5 months and 9 days, was the youngest head coach to win a Super Bowl. Before returning to coaching in 2018, he served as an analyst for ESPN and "Monday Night Football".