Pittsburgh Steelers free agency trade March Madness 2025: Elite 8

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It’s the fourth week of Steelers March Madness, our annual NCAA-style journey through black and gold history. This year’s theme is the 64-best front office moves in Steelers history. It’s time to vote on the Elite 8!

Pierogi Bracket

Pierogi Bracket ‘25, Elite 8

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.

3 seed: October 3, 2015 – Signed free agent kicker Chris Boswell

(signed two-year, $960,000 deal)

Photo by Justin K. Aller/Getty Images

Yinz really picked Boswell over trading up for Santonio Holmes in the Sweet 16?!

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.

Poll

Better Front Office Move?

94%

1: Trade for Bettis

(32 votes)

3: Sign Boswell

(2 votes)

34 votes total

Vote Now

Halupki Bracket

Halupki Bracket ‘25: Elite 8

1 seed: April 26, 2003 – Traded up to draft safety Troy Polamalu

(Traded 1st round pick (27th overall, Larry Johnson), 3rd round pick (92nd overall, Julian Battle) and 6th round pick (200th overall subsequently traded, Brooks Bollinger) to Chiefs for 1st round pick (16th overall, Troy Polamalu)

Photo by Joe Sargent/Getty Images

Pittsburgh was almost not in the market for a safety in 2003. The Steelers had a verbal agreement with Dexter Jackson, the reigning Super Bowl MVP, but he would end up signing with Arizona. Polamalu was the top-ranked safety in the draft. When San Diego traded down at pick 15 instead of addressing the safety position, Pittsburgh traded up from 27 to 16 with the Chiefs. The Steelers traded away the 92nd and 200th overall picks.

2 seed: February 14, 2000 – Signed free agent nose tackle Kimo Von Oelhoffen

(signed a four-year, $11 million deal)

Photo by George Gojkovich/Getty Images

Kevin Colbert’s first free agent signing as the Steelers’ general manager. Von Oelhoffen spent six years in Cincinnati as a nose tackle, but Pittsburgh soon converted him to defensive end. He started 94 games for the Steelers including Super Bowl XL.

Poll

Better Front Office Move?

100%

1: Trade up for Troy’s pick

(32 votes)

2: Von Oelhoffen signing

(0 votes)

32 votes total

Vote Now

Chipped Ham Bracket

Chipped Ham Bracket ‘25: Elite 8

1 seed: April 5, 2002 – Signed free agent linebacker James Farrior

(Signed a three-year, $5.4 million deal)

Photo by George Gojkovich/Getty Images

Farrior was the 8th overall pick in the 1997 draft, but the Jets used him as an outside linebacker. New York was not interested in extending him after his rookie contract, despite putting up career numbers in 2001. Farrior says he received no other offers besides Pittsburgh. He went on to start 154 games at inside linebacker.

2 seed: March 8, 2001 – Signed free agent center Jeff Hartings

(signed a six-year, $24.2 million deal)

Photo by George Gojkovich/Getty Images

Former general manager Kevin Colbert was with Detroit when the Lions drafted Hartings. Although Hartings played guard in the NFL, Colbert knew he could play center, and replace the retiring Dermotti Dawson. Hartings went on to make two Pro Bowls and one All-Pro team during his 89 starts in Pittsburgh.

Poll

Better Front Office Move?

91%

1: Farrior signing

(31 votes)

2: Hartings signing

(3 votes)

34 votes total

Vote Now

Banana Split Bracket

Banana Split bracket ‘25: Elite 8

1 seed: April 3, 1993 – Signed free agent linebacker Kevin Greene

(signed a three-year, $5.35 million deal)

Greene came to Pittsburgh in free agency because of Defensive Coordinator Dom Caper’s 3-4 system. He didn’t come cheap. He was the highest-paid Steelers defender ever at the time. Greene was only in Pittsburgh for three seasons, but in those 48 games, he earned 35.5 sacks, two Pro Bowls, and an All-Pro season in 1994. He played in two AFC Championship games for Pittsburgh and one Super Bowl.

2 seed: March 14, 2006 – Signed free agent safety Ryan Clark

(signed a four-year, $7 million deal)

Set Number: D153547 TK1 R1 F32

After two seasons, Washington cut Clark but was willing to bring him back on a smaller, minimum contract. R.C. felt disrespected, so he chose to test the market. Pittsburgh was his only offer. Clark went on to play in 80 games, starting 78, and made three Super Bowl appearances.