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Choosing the best front office moves in Steelers history
Welcome to the Sweet 16 of Steelers March Madness ‘25. This year’s theme is the greatest front office moves in Pittsburgh Steelers history. You choose which moments move on until we crown a champion. Today, let’s look at the Pierogi Bracket!
PIEROGI BRACKET

1 seed: April 20, 1996 – Traded for running back Jerome Bettis
(Traded 2nd round pick (59th overall, Ernie Conwell) and 1997 4th round (121st overall later traded, Jerome Daniels) to Rams for Bettis and 1996 3rd round (72nd overall, Steve Conley)

SetNumber: X64443 TK2 R5 F12
In one of the most lopsided transactions in NFL history, Pittsburgh moved down 13 spots from pick 59 to 72 and added a future 3rd rounder in exchange for Jerome Bettis. The Rams were transitioning to a pass-oriented offense and drafted Nebraska’s Lawrence Phillips. St. Louis gave Bettis the option to pick his destination, and he almost considered Houston. Writers in Pittsburgh didn’t love the trade initially, because Bettis had a pair of down seasons and his contract was up at the end of the year. But they changed their tune after The Bus won Comeback Player of the Year and became the highest-paid player in Steelers history at that point.
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5 seed: April 5, 1993 – Signed free agent quarterback Mike Tomczak
(signed three-year, $2.55 million deal)

Photo by Focus on Sport/Getty Images
By the time Neil O’Donnell cemented his position as starting quarterback, it was time for the Steelers to move on from Bubby Brister. They needed a new backup, and Tomczak saw Pittsburgh as his best opportunity for playing time. He stayed for seven seasons, starting nearly all of 1996, including two playoff games.
2 seed: April 29, 2006 – Traded up to draft receiver Santonio Holmes
(traded 1st round pick (32nd overall, Mathias Kiwanuka), 3rd round pick (96th overall, Gerris Wilkinson), and 4th round pick (129th overall, Guy Whimper) to Giants for 1st round pick (25th overall, Santonio Holmes)

SetNumber: X78614 TK1 R3
Holmes was one of the players Kevin Colbert had his eyes on at the start of the 2006 draft. When he was still available at pick 20, Colbert started making calls. The Chiefs weren’t interested in trading at 20. Neither were the 49ers at 22, but the Giants made the deal at 25. In his four seasons in Pittsburgh, Holmes had 3,835 receiving yards, 20 touchdowns, and one of the most iconic Super Bowl moments ever.
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3 seed: October 3, 2015 – Signed free agent kicker Chris Boswell
(signed two-year, $960,000 deal)

Photo by Justin K. Aller/Getty Images
In Week 4, kicker Josh Scobee missed two fourth-quarter field goals in an overtime loss to the Baltimore Ravens. He was released two days later and replaced with Boswell. Since then, Boswell has played in 150 games in the black and gold and has more 50-yard field goals than all other Steelers’ kickers combined.
We’re back tomorrow with the Halupki Bracket’s Sweet 16, and the biggest Cinderella remaining in the tournament!