The Pittsburgh Steelers have been one of the league's most consistently successful franchises of the last thirty years. In fact, the Steelers have only had four season with a regular season record below .500 dating back to 1991. One reason for this success is a successful front office that makes smart decisions during free agency and the NFL Draft. Former Steelers GM Kevin Colbert made a ton of great decisions for Pittsburgh over a 20+ year span, but we recently shared his biggest regret of missing on a legendary NFL player.

Colbert appeared on a recent episode of Cameron Heyward's podcast, Not Just Football with Cam Heyward. Heyward and Colbert talked during the Steelers draft part on day three of the 2024 NFL Draft. They discussed several topics, including Colbert's biggest regret as Steelers GM.

“There's always guys you're going to look at and say, ‘Wow, in the whole universe, we missed on Tom Brady,'” Colbert said, “that's a living, breathing, walking legend.”

Regretting passing on Tom Brady is the oldest trick in the book. It's right up there with claiming you were high on Patrick Mahomes in the 2017 NFL Draft. However, Colbert was closer than most to actually selecting Brady in 2000. Pittsburgh selected QB Tee Martin 163rd overall, just 36 spots ahead of Brady.

“Going in the sixth round, that's unusual, that doesn't happen too often. Then we ended up chasing him. We had our own successes, but obviously Tom Brady had a lot of successes. The Patriots did great putting together successful seasons, and that's the challenge of the endeavor. If you ask me for one, I'll always go with that because that was my first year here.”

Colbert served as the Steelers GM from 2000 through the 2022 NFL Draft.

Remembering the Ben Roethlisberger era of the Pittsburgh Steelers

Pittsburgh Steelers quarterback Ben Roethlisberger (7) pump fakes the ball by Seattle Seahawks linebacker Benson Mayowa (10) during the fourth quarter at Heinz Field.
© Philip G. Pavely-USA TODAY Sports

Steelers fans may be sad to learn that they missed out on Tom Brady, but they didn't have to wait long to find another franchise QB.

Pittsburgh selected Ben Roethlisberger with the 11th overall pick in the 2004 NFL Draft. It was the highest draft pick the Steelers used on a quarterback since 1970 when they picked future Hall of Famer Terry Bradshaw first overall.

Roethlisberger made a strong impression on Pittsburgh during his rookie campaign. He went 13-0 during the regular season and led the Steelers to a near-perfect 15-1 record. He also delivered a Divisional Round playoff victory over the Jets and played well in a tough AFC Championship loss against — of course — Tom Brady and the New England Patriots.

Despite that loss, the future was bright in Pittsburgh. Roethlisberger won Offensive Rookie of the Year and set their sights on the Super Bowl.

Over the next six seasons, the Steelers made three Super Bowl appearances and won two Lombardi Trophies.

Pittsburgh was always relevant throughout the Ben Roethlisberger years, making several playoff appearances in the twilight of his career but never making it back to the Super Bowl. The closest they came was in 2016 when they lost in the AFC Championship again to the Brady-led Patriots.

Roethlisberger finished his NFL career with 64,088 passing yards, 418 TDs, and 211 INTs.