The Pittsburgh Steelers are at a crossroads two years into the post-Ben Roethlisberger era. It was not supposed to be like this. The Steelers used pick number 20 in the 2022 NFL Draft to select Kenny Pickett, much to the delight of many Pittsburgh faithful. Pickett was the best quarterback since Dan Marino for the Pittsburgh Panthers, and the organization refused to let him escape to another team.
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Jordan Schofield / SteelerNation (X: @JSKO_PHOTO)
Pittsburgh Steelers quarterback, Kenny Pickett (8).
It hasnโt worked out. At least not yet. Pickett would not be the first quarterback to take a little time to figure it out in the NFL. The good news is that Pittsburgh did not pay a hefty price for him. He was saddled with Matt Canada, arguably the worst offensive coordinator in the organization's history, and he regressed instead of progressed in his second season.
Steelers' Art Rooney II Has Revealing Answer About Pittsburgh Trading For A Quarterback
Art Rooney II has gone viral for his comments to Bob Pompeani in an interview with KDKA for not ruling out a trade for a veteran quarterback. The interview ignited the already substantial social media speculation on a possible trade for Justin Fields on Wednesday into an inferno. It is an intriguing possibility, but here are five questions that Khan must consider as part of a necessary checklist before pulling the trigger on a paradigm-shifting trade for the Steelers.
Item 1 - Is Kenny Pickett A Starting Caliber NFL Quarterback?
Head Coach Mike Tomlin said his opening-day starter for 2024 was on the roster at his season-ending press conference. He knew Mason Rudolph was a free agent and not on the roster, so he had to mean Pickett. Tomlin hired Arthur Smith as his offensive coordinator, and the subject of the former first-round pick's chances to become an effective NFL quarterback had to be part of the interview.

David J. Phillip / AP Photo
Pittsburgh Steelers quarterback Kenny Pickett (8) is helped off the field after an injury during the second half of an NFL football game against the Houston Texans, Sunday, Oct. 1, 2023, in Houston.
The fact is that Pickett's play is not the biggest issue in evaluating his future. He has left five of his 25 career starts due to injury. The most important ability in the NFL is availability, and so far, Pickett has yet to demonstrate he has it. It is possible that his play improves in Smith's bootleg play-action game, but if he can't stay on the field, it won't matter very much.
Item 2 - Are The Steelers Comfortable Moving On From Mason Rudolph?
This was not a hard question to answer before the last three games of the 2023 regular season. Rudolph was essentially an NFL castoff who was planning for life after football. No other team was interested in signing him before the 2023 season, and he signed a one-year contract to be the emergency quarterback for the Steelers. Rudolph's eyes were wide open. He would get paid a lot of money to stand on the sidelines in uniform for one more season.

Rob Carr / Getty Images
Pittsburgh Steelers quarterback Mason Rudolph (2) could be out of the Steelers' price range in 2024.
Rudolph got an opportunity when the Steelers collapsed with virtually no hope of making the playoffs. Tomlin inserted him into the lineup against the Cincinnati Bengals in Week 16 as the starter. He played like he had nothing to lose and engineered a three-game winning streak to help the team secure the seventh seed in the AFC. He also earned another opportunity in the NFL. He demonstrated he might be a viable bridge quarterback who could be out of the Steelers' price range in free agency. If they trade for Fields, retaining Rudolph will be tough.
Item 3 - Would The Steelers Be Comfortable With Mitch Trubisky As The Primary Backup Option In 2024?
No. In other news, H2O in liquid form is apparently wet.
Mark Kaboly of The Athletic has shared that he thinks this is possible. Maybe it is, but the fan reaction would be priceless if Trubisky somehow makes it into a regular season game at Acrisure Stadium in 2024. Dumping Trubisky and his salary to acquire Fields should be a huge yes for the fan base. Dumping Trubisky and his salary for Pittsburgh Penguins season tickets is a tough call, but it is an all too acceptable outcome if they are good seats.
Item 4 - Is Justin Fields Available To The Steelers?
The Chicago Bears are reportedly set to dump Fields to draft Caleb Williams with the first pick in the 2024 NFL Draft. There is one big problem. Williams allegedly does not want to play in Chicago. He is channeling his inner John Elway/Deion Sanders and trying to force his way to another NFL city. If he is successful, he will be the first quarterback since Eli Manning to pull it off.

Ashlee Rezin / Sun-Times
Steelers' possible trade target is the Chicago Bears quarterback, Justin Fields (1).
Mike Florio thinks the Bears should keep Fields and build around him, but has embraced the reality that the Bears are moving on. If Williams maintains his posture, there will be high drama in Chicago. Currently, arguably the second-best quarterback in the 2024 class is Drake Maye. Would the Bears potentially dump Fields to Khan and the Steelers after the Chase Claypool debacle to draft the quarterback from North Carolina? Even the Bears might reconsider if that is the primary option.
Item 5 - Is Justin Fields The Final Answer To The Steelers Quarterback Question?
Steeler Nation is split on Fields. A large faction points to his propensity for turning the ball over. Fields is a running quarterback who fumbles entirely too often. He also rushed for 1,000 yards in a season and made huge strides as a passer in the second half of 2024, with DJ Moore and Cole Kmet emerging as reliable weapons.

AP
Steelers have a chance to obtain Justin Fields in the 2024 offseason.
Fields is only 24 years old. He is younger than Pickett, only one year older than Jayden Daniels and Bo Nix, and the same age as Michael Penix Jr. He has started 38 NFL games for some bad Bears teams and has gotten progressively better each season as a passer. The Steelers must pick up a fifth-year option that will cost the team $23.3 million. However, the Steelers will essentially be paying him approximately $27 million for two seasons, a bargain for a starting NFL quarterback who will only be 26 years old at the end of his fifth season.
Peter King from Football Morning In America relentlessly advocates for the Steelers to sign Russell Wilson. There is virtually no upside for Pittsburgh to sign quarterbacks in their late 30s. If Fields were in the 2024 NFL Draft class, he would be outside the Steelers' reach at pick 20. It is not a slam dunk that he will succeed as the Steelers quarterback, but the question is if he is better than Pickett, Trubisky, and potentially a returning Rudolph. If the answer is yes, Khan should pull the trigger. Just at what cost?
What do you think, Steeler Nation? Should the Steelers pull the trigger on a Fields trade? Please comment below or on my Twitter/X: @thebubbasq.
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