The Pittsburgh Steelers did not make too many trades in the Kevin Colbert era. He was one of the more conservative general managers of his time. The 2019 year was the only one when he really went super aggressive, and that was greatly influenced by his eventual replacement, Omar Khan. Most of Colbert's deals involved giving up or receiving day three draft picks in under-the-radar deals. However, he had one trade early in his tenure that is still having an effect on Pittsburgh to this very day.

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Pittsburgh Steelers former GM Kevin Colbert oversaw Pittsburgh's drafts from 2000 until 2022
After the Steelers won Super Bowl XL, Colbert made a draft-day trade to try and win another. He moved up from the 32nd pick to the 25th to draft wide receiver Santonio Holmes, giving up a third- and fourth-round pick in that same draft to get it done. The only player involved in the deal that they really missed out on was Mathias Kiwanuka, who had a productive career with the New York Giants.
Holmes would go on to win Super Bowl XLIII MVP after a great performance capped off by a legendary game-winning catch in the corner of the end zone. Even though he did not spend a lot of time in Pittsburgh, he will always be one of the greats because of his involvement in securing championship number six. It can be argued that his is the greatest catch in Super Bowl history.
However, the Steelers were quick to trade Holmes away after he got suspended for "substance abuse." He was shipped off for merely a fifth-round pick in 2010. The Steelers would flip that pick to the Arizona Cardinals in exchange for a sixth-round pick and the return of Bryant McFadden. That sixth-round pick was used to select the greatest wide receiver of his generation: Antonio Brown.

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Before Antonio Brown became one of the best NFL wideouts of all-time, he was a prolific returner in the early years of his career.
Brown needs no introduction. He quickly made his way up the depth chart thanks to amazing catches and expert-level route running. He was one of the many reasons why the mid-2010s Steelers had one of the best offensive teams in franchise history. His antics grew along with his stat sheet, and that led to him being traded away in 2018 for more than the organization got via the previous deal.
He was traded away in exchange for a third- and fifth-round pick. The former of the two selections was used to draft Diontae Johnson, another expert at running routes. He and Brown were in rare company of wideouts that received a second contract with the team. However, it wasn't all sunshine and rainbows for Johnson, either.
Steelers Continued With The Same Trade Tree In 2024
Johnson was also a malcontent, which resulted in him getting traded in 2024 in exchange for Donte Jackson and a late-round pick swap. Johnson's issues became more apparent has he was traded away for another swap of day three selections. This was also Khan's first entry into this prolific trade tree.

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Steelers' Donte Jackson celebrates with his teammate Elandon Roberts after a huge play.
Jackson spent one year in Pittsburgh, where he became a turnover machine and a quality cornerback option. However, injuries kept holding him back, which forced the Steelers to let him walk in free agency. With the sixth-rounder Pittsburgh received in the Johnson deal, the team selected Logan Lee.
He missed all of his rookie season due to injury. He may be a backup fighting for a roster spot, but he is the last remaining piece of the trade on the Steelers' end of things. However, the tree continues elsewhere.
Throughout this timeline, the Steelers had one prolific wideout lead the team to a Super Bowl victory, another amazing receiver getting Pittsburgh into another one thanks to a ridiculous helmet catch to cap off a playoff comeback, and two other quality players that helped the Steelers fill a need. Holmes' time in Pittsburgh may have been short-lived, but the cause-and-effect of Colbert trading up for him is still felt to this day.
Johnson was traded from the Carolina Panthers to the Baltimore Ravens shortly after he arrived in Carolina. A fifth- and sixth-round pick were exchanged in the deal, which will be used in 2025. Who knows if those picks will be used on quality contributors or not, but for now, the Holmes trade tree will grow a couple more branches before all is said and done.
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