He began his coaching career as an assistant under Marty Schottenheimer for the Cleveland Browns and Kansas City Chiefs, serving as the latter's defensive coordinator from 1989 to 1991.

Cowher's Super Bowl victory marked the first championship title for the franchise in over two decades and the first not to be won by Chuck Noll, his predecessor.

His father attended Duquesne University in Pittsburgh's south side neighborhood[2] where he was briefly a classmate with eventual Steelers owner Dan Rooney.

Despite his efforts on the field, Cowher was not offered many scholarships as a football player due to being deemed "undersized" for the linebacker position.

[citation needed] Cowher began his coaching career in 1985 at age 28 under Marty Schottenheimer with the Cleveland Browns.

[12] He was a finalist for the Cincinnati Bengals head coaching position in 1991 following the dismissal of Sam Wyche, but was passed over in favor of Dave Shula.

His first season as a head coach came to an end in the AFC Divisional round on January 9, 1993, against the Buffalo Bills in which the Steelers would lose 24–3.

[17] In the 1995 regular season, Cowher got the team to record 11 wins and five losses, once again sending them to the playoffs and earned them a first round bye.

[18] The Steelers were able to defeat the Buffalo Bills, who were coming off of four straight Super Bowl appearances, 40–24 and recorded a 20–16 victory against the Indianapolis Colts.

During his tenure, the team had mixed results with this strategy, drafting future Hall of Famer Alan Faneca and future Pro Bowlers Leon Searcy & Casey Hampton but also drafting Jamain Stephens (who would go on to be one of the team's biggest first-round busts) and Kendall Simmons (a solid starter but plagued by injuries and a sudden diagnosis of type 1 diabetes), with Stephens infamously being cut after failing the 40-yard dash on the first day of training camp.

Defendants of this strategy pointed out that of the five lineman drafted, only Stephens was a bonafide bust and of the skill position players the Steelers did draft with their first round picks (Deon Figures, Charles Johnson, Mark Bruener, Chad Scott, Troy Edwards, and Plaxico Burress), with the exception of Bruener and to a lesser extent Scott and Burress largely didn't live up to expectations, though only Edwards would be a bust.

[22] Cowher did not initially want to select Roethlisberger in the first round as he was "comfortable" with starter Tommy Maddox and backup Charlie Batch.

The Steelers would make another AFC Championship appearance, losing 41–27 to eventual Super Bowl champions the New England Patriots.

[26] The Steelers led an upset playoff run, including a 21–18 victory over the Indianapolis Colts, the top seeded team in the AFC.

Including the Super Bowl, Cowher's teams over the years had compiled a record of 108–1–1 in games in which they built a lead of at least 11 points.

On January 11, 2020, Cowher was told live on a CBS pregame show that he was being inducted into the Pro Football Hall of Fame as part of its centennial class by its president David Baker.

Unlike the conservative Schottenheimer, however, Cowher was known to take more risks, including going for it on fourth down, such as his first game as a head coach against the Houston Oilers when he had punter Mark Royals throw a fake punt to Warren Williams and putting the Steelers near the goal line.

[34] On February 15, 2007, he signed on to The NFL Today on CBS as a studio analyst, joining Dan Marino, Shannon Sharpe, and Boomer Esiason.

"[36] The rumors started after the Cowhers placed their Raleigh, North Carolina home on the market, but their intention was to build a new house two miles away.

[38] Cowher had a part in the movie The Dark Knight Rises (2012), which was filmed at Heinz Field, the home of the Steelers, on Pittsburgh's North Side.

[40] On August 11, 2023, NC State announced that Cowher would be inducted into its Ring of Honor with the ceremony taking place before the Wolfpack's September 29 game versus Louisville.

Kaye was featured in the book Mad Seasons: The Story of the First Women's Professional Basketball League, 1978–1981, by Karra Porter (University of Nebraska Press, 2006).

[45] In 2018 Cowher put his Raleigh house in North Ridge Country Club up for sale after announcing he would be moving to New York full-time.