Chicago Tribune

What if Bears had been able to lure Tom Brady in 2020 — how aggressively did they pursue the QB?

CHICAGO — Jake Gellerman thought very little of the initial text. His brother-in-law needed a favor, and he hoped he could help.

Yeah, man. What do you need?

Mike Greenberg was down in Florida and needed to get some paperwork to a new hire, who was at his home in New York. So Greenberg fired the request and Gellerman agreed to assist, rolling to a Staples near his Manhattan apartment and printing a handful of forms from his email.

Then he pulled up his Uber app, typed in his destination in Tribeca and took a deep breath as he waited for his driver, Satparkash, to take him on a seemingly routine $34.29 ride.

Perhaps now is where we should mention Gellerman’s brother-in-law is in the front office for the Tampa Bay Buccaneers. And that the special-delivery assignment that evening was taking him to the residence of a prospective Bucs employee named Tom.

Yep. That Tom. Pretty well-known in NFL circles and amazingly unemployed after his longtime job near Boston came to an abrupt end.

Waiting for his Uber, Gellerman still was processing it all, wondering first what the other Staples patrons were up to.

You’re buying file folders and highlighters? Photocopying tax documents? Well, guess what. I’ve got Tom Brady’s new contract in hand.

“Just got a $50 million deal here, you know?” Gellerman said.

It was March 18, 2020, which otherwise might have been a standard Wednesday, except it was the opening day of NFL free agency in the early stages of an intensifying pandemic. The sports world was among the many operations that suddenly had shut down the previous week because of concerns about COVID-19. Work-from-home directives were spreading across many businesses, including the NFL.

The Buccaneers, with urgency to land a new quarterback, couldn’t get Brady to their team facilities to take a physical and sign his contract amid travel restrictions and distancing guidance. So Gellerman, the 29-year-old brother-in-law of the team’s director of football administration, became a key pinch hitter, commuting to

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