He was previously the announcer for the Colorado Gold Kings of the West Coast Hockey League (WCHL) from 1999 to 2002, and the Alaska Aces of the ECHL from 2002 to 2010.

"[5] He was inspired by the fast-paced commentary of Penguins broadcaster Mike Lange,[5] who he compared to announcer Dave Johnson in horse racing, another sport he grew up watching.

[4][7] Michaels graduated from Meadville Area Senior High School in 1991,[4] and attended Ithaca College to pursue broadcasting.

[1]: 9:10  In his first week of school, he successfully auditioned to be a newsreader and sports announcer for the Sunday morning sportscast on WICB, the college's larger radio station.

[1]: 17:03 In the spring of 1999, Michaels announced the Penguins Cup final between the Meadville Bulldogs and the Central Catholic Vikings,[11][12] which he has described as a turning point in his career.

[4] Michaels started in Colorado Springs as the Gold Kings' director of broadcasting in August 1999, calling the team's games on KKCS (1460 AM).

[3][5] According to Michaels, he was desperate at the time, as job opportunities would be filled with training camp starting in a month,[18] and believed he was "not well established enough to take a year off".

[19][12] Nonetheless, of the two options, Michaels believed the Aces had more potential with its devoted fan base, and accepted the offer to work in Anchorage.

[25] Michaels continued his work with the Aces and announced the 2004 ECHL All-Star Game, with Neil Smith as colour commentator.

[27] During the 2006 ECHL West Division Finals in May 2006, Michaels became known for his call of the Aces' 4–3 triple-overtime win over the Las Vegas Wranglers, in a game that lasted almost five hours.

"[5] In 2007, an Aces home game at Sullivan Arena was attended by the singer Steven Tyler,[30] who joined Michaels in the third period as his colour commentator.

[3][5] He had previously unsuccessfully applied for the position with the Florida Panthers and New York Islanders, and was doubtful an American would be hired by a Canadian team, based on tradition and issues with immigration.

He recounts making the sudden decision to apply while driving his family to Long Island, which led him to turn around and mail in a rushed application.

[5] He also subsequently attributed the success of his application to a positive recommendation from a former Alaska Aces player that lived next to a member of the Oilers' hiring committee, and his inclusion of NBC national ice hockey announcer Mike Emrick on his reference list.

[40][41] His second TV appearance was for a Los Angeles Kings home broadcast in April 2017, as one of a series of fill-in announcers for Bob Miller, who had experienced health problems and was due to retire at the end of the season.

[1]: 32:52  The Colorado Gold Kings folded three months later, leading Michaels to leave for a job in Anchorage, Alaska while Emily stayed behind to fulfill her commitment as a teacher for the local school district.