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While he wasn't known as a gambler, Kevin Colbert made his share of risky moves during his 22 drafts as the Pittsburgh Steelers general manager. Most of the time, the risks Colbert made paid off handsomely while contributing to the Steelers' two most recent Super Bowl wins. His successor, Omar Khan, is hoping to have similar success if he decides to trade up in the first round of this year's NFL Draft. 

While first-round trades often come as a surprise, the Steelers trading up in the first round in this year's draft is almost expected. In fact, CBS Sports NFL Draft analyst Ryan Wilson has heard from sources that the Steelers could trade up to try to select Ohio State's Paris Johnson Jr., who is one of the top-ranked offensive tackles in the draft. 

As mentioned above, the Steelers had considerable success when they moved either up or back in the first round during the Colbert era. Let's take a look at each of those transactions and how it impacted the Steelers in the following years. 

2001

  • Traded No. 16 pick to Jets for 19th pick, 111th pick and 181st pick 

For the only time in the Colbert era, the Steelers traded back in the first round. With the pick, the Steelers acquired nose tackle Casey Hampton, who ended up being a major piece on what would be the NFL's best defense for nearly a decade. With Hampton in tow, the Steelers' defense permitted the NFL's fewest points on four separate occasions. The 2008 squad allowed an average of just 13.9 points per game en route to winning the franchise's sixth Super Bowl title. 

A five-time Pro Bowler, Hampton won two Super Bowls and three AFC titles during his 12-year career. An extremely durable player, Hampton made 164 regular-season starts and 15 playoff starts. He recorded a big sack late in Pittsburgh's win over Seattle in Super Bowl XL. 

2003

  • Traded No. 27 pick, 92nd pick and 200th pick to Chiefs for No. 16 overall pick 

The Steelers entered the draft in need of a safety after they tried to sign reigning Super Bowl MVP Dexter Jackson in free agency. After missing out on Jackson, Colbert and Co. were not about to miss out on drafting Troy Polamalu, a standout at USC who was the first Trojan since Tony Boselli in 1992 to be a two-time All-American. 

While his rookie season was difficult, Polamalu quickly blossomed into an All-Pro level player in Pittsburgh. He was named to his first of five straight Pro Bowls in 2004 while helping the Steelers go 15-1 during the regular season. In 2005, Polamalu put on a clinic during the postseason while helping the Steelers become the first six-seed to win the Super Bowl. His pick-six in the 2008 AFC Championship Game helped the Steelers win their sixth Super Bowl. 

In 2010, Polamalu joined Joe Greene, Mel Blount, Jack Lambert, Rod Woodson and James Harrison as Steelers players to win Defensive Player of the Year. A decade later, Polamalu earned the rare distinction of being a inducted into the Pro Football Hall of Fame in his first year of eligibility. 

2006

  • Traded No. 32 pick, 96th pick and 129th pick to Giants for No. 25 overall pick  

Not many people expected the Steelers to trade up months after winning the Super Bowl. But the Steelers did just that while acquiring Ohio State wideout Santonio Holmes. Holmes offered a foreshadow of future brilliance on the final play of his rookie season. In Bill Cowher's final game as Steelers coach, Holmes turned a slant pass into a game-winning, 67-yard touchdown in overtime in Pittsburgh's regular-season finale in Cincinnati. 

Holmes played an integral role in Ben Roethlisberger's first Pro Bowl campaign in 2007. Holmes caught eight of Roethlisberger's then-franchise-record eight touchdown passes that season while leading the NFL in average yards per reception. Holmes' career really took off in 2008, when he won MVP honors after making the game-winning catch in Pittsburgh's win over Arizona in Super Bowl XLIII. Holmes' 2008 season also included touchdowns in each of the Steelers' other two playoff games as well as his game-winning touchdown catch in a late-season win over Baltimore. 

Holmes followed up his 2008 season by setting career highs with 79 receptions for 1,248 yards in 2009. But issues off the field led to the Steelers trading Holmes before the 2010 season. Holmes, who spent the next four seasons with the Jets and an additional season with the Bears, officially retired as a member of the Steelers' organization in 2017. 

2019

  • Traded No. 19 pick, 52nd pick and 83rd pick to Broncos for No. 10 overall pick 
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Devin Bush
CLE • LB • #30
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This initially looked like another gem of a trade for Colbert and Co. Devin Bush, an All-American linebacker at Michigan, enjoyed a solid start to his pro career that included two interceptions, four fumble recoveries, a forced fumble and a defensive touchdown during his rookie season. Bush was off to a similar start in 2020 before suffering a season-ending knee injury after just five games. 

Bush was never the same in Pittsburgh following the injury. He seemed unsure of himself and was often out of position to make plays during the 2021 season. That prompted the Steelers to decline picking up his fifth-year option ahead of the 2022 season. Bush played better in 2022, but he ultimately signed with Seattle in free agency after the Steelers let him test the market. 

2020 

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Minkah Fitzpatrick
PIT • FS • #39
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It's hard to fathom now, but many people actually criticized Colbert in the moment for trading Pittsburgh's 2020 first-round pick to Miami in exchange for Minkah Fitzpatrick two weeks into the 2019 season. At that point in time, the Steelers were 0-2 and were facing a lost season after losing Roethlisberger to a season-ending injury in Week 1. 

While many were critical, Cowher lauded the trade for Fitzpatrick, who was looking for a fresh start after Miami mismanaged the start of his career. 

"Sean Davis hasn't been able to stay healthy there, and Minkah Fitzpatrick is a very good football player, a proven player who has been in this league for a year now," Cowher said at the time. "He's young, he has multiple years on his contract. He gives you a lot of versatility from the standout of that he can play a lot of different positions and lot of different roles." 

Cowher's comments quickly proved to be prophetic. Fitzpatrick had 14 tackles, a forced fumble and an interception during his first game as a Steeler. He earned the first of his three All-Pro selections with the Steelers that season while helping Pittsburgh go 8-8 that season after an 0-3 start. 

Still just 26 years old, Fitzpatrick was rewarded with a four-year extension during the 2022 offseason. Fresh off of his new deal, Fitzpatrick received another All-Pro nod in 2022 while helping the Steelers secure their 19th consecutive non-losing season.