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.
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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 a luxurious building in New York with specific marching orders.
Just tell the doorman you're there to see Tom. Then help finish the deal.
Gellerman got the green light and was buzzed in. Up he went. Lo and behold, there was Brady, ready to sign his landmark two-year, $50 million agreement from the island in his kitchen.
"At a weird time in the world," Gellerman said, "I was just happy I could be helpful on something that was pretty important to everyone involved. It's the one and only contract I've ever helped execute. A good high to go out on probably."
Even if he didn't realize it in the moment, Gellerman was serving as a chance courier on arguably the most momentous NFL contract of the Super Bowl era. At the very least, it was one of the most pivotal, changing the league's entire competitive landscape.
Think about it: When March 2020 began, the Buccaneers were a sputtering 7-9 team with quarterback issues and a 13-season playoff drought. They had finished in the bottom half of the NFC South 11 times in 12 seasons. They were wayward and seeking direction.
Now, in October 2021, the Bucs are the NFC favorites, in prime position to repeat as Super Bowl champs as they prepare to host the Chicago Bears at Raymond James Stadium on Sunday.
Brady's old team, the New England Patriots, lost its way in its first season without him and still is battling to regroup. The Patriots finished 7-9 last year, snapping a streak of 11 consecutive AFC East championships and posting their first losing record since 1995, when Brady was a freshman backup at Michigan and Bill Belichick was a floundering coach with the Cleveland Browns.
A reboot, with rookie Mac Jones at quarterback, has produced a 2-4 start for the Patriots this year.
In Chicago, meanwhile, the Bears seem permanently tethered to their maddening .500 existence, now 3-3 after back-to-back 8-8 seasons. Even with recent flashes of promise from rookie quarterback Justin Fields, the idea of playing for a Lombardi Trophy anytime soon seems far-fetched.
But what if the Bears had been able to lure Brady to Chicago 19 months ago? How aggressively did they even pursue that dream at a time when their quarterback fortunes were low and the greatest of all time was seeking a new opportunity? And what ultimately sent Brady to the Bucs instead?
'I'm going to (bleep) you up'
Who the hell was Team X?
That was the mystery social media sleuths were frantic to solve this summer when Brady was heard from a chair in an undisclosed barbershop discussing one of his potential 2020 free-agency suitors and the commitment it expressed toward an unnamed quarterback.
"One of the teams, they were interested," Brady said. "And then all of a sudden they weren't interested at the very end. I'm sitting there thinking, 'You're sticking with that (expletive)? Are you serious?' "
Granted, Brady was knowingly mic'd up in that chair, a guest on HBO's series "The Shop" and sitting alongside rapper Kid Cudi, comedian Chelsea Handler and NBA All-Star Draymond Green. And while the quarterback was careful not to specify which franchise and starting quarterback he was alluding to, he tacked on this ice-cold parting shot.
"When I look back, I'm thinking, 'There ain't no (bleeping) way I would have went to that team,' " he said. "
But they said they didn't want me. And I know what that means, I know what that feels like. And I'm going to (bleep) you up because of that."
That wasn't a threat. It was a promise.
Could Brady have been alluding to Bears general manager Ryan Pace and then-quarterback Mitch Trubisky? Who else could have possibly fit such a description?
Derek Carr and the Las Vegas Raiders? Ryan Fitzpatrick and the Miami Dolphins? Perhaps Jimmy Garoppolo and the San Francisco 49ers or Ryan Tannehill and the Tennessee Titans?
That mystery might remain forever unsolved, still open to widespread outside conjecture. The only rumor even suggesting that a Brady-Bears union was realistic came via "The Dan Patrick Show" in September 2020. Via feedback from an anonymous source, Patrick asserted the Bears were on Brady's free-agency short list along with the Bucs and Los Angeles Chargers.
"I said, 'Wait a minute. The Bears?' " Patrick said. "(The source) told me yes."
Inside many league circles, however, the notion that Brady seriously considered playing for the Bears is often dismissed. And quickly. Besides an established defense and a big-city stage, what did the Bears really have to attract Brady? They were coming off an abysmal offensive season in which they finished 29th in total yards and 25th in passing offense.
Matt Nagy, the team's coach and offensive architect, had done little to establish himself as a quarterback catalyst. The Bears also had just fired offensive coordinator Mark Helfrich, offensive line coach Harry Hiestand and tight ends coach Kevin Gilbride Jr. And with a shortage of top-tier playmakers and a pedestrian offensive line, many inside the league believe the Bears offense would have had minimal appeal to Brady.
Furthermore, the prevailing sense was Brady also wanted to finish his career in a warmer climate, leaving him most intrigued by the possible openings in Tampa, Los Angeles and San Francisco, near where he grew up.
However everything unfolded, on the afternoon Brady closed on his new deal with the Bucs, the Bears reshuffled their quarterback situation, trading a fourth-round pick to the Jacksonville Jaguars for veteran Nick Foles and envisioning an open competition for their starting job: Foles versus Trubisky.
That was, for the record, the second time the Bears had missed out on Brady. They were one of 30 teams who passed on him in the 2000 draft. For six rounds.
Under then-vice president of player personnel Mark Hatley, the Bears selected seven players while Brady was still on the board. Late on the draft's second day, in the round in which the Patriots selected Brady at No. 199, the Bears went for Kansas State receiver Frank Murphy (No. 170) and Michigan State kicker Paul Edinger (No. 174).
At the time, no one knew the winning lottery ticket that had blown past. Twenty years later, however, in the Brady free-agency sweepstakes, a known jackpot was attached.
Ultimately, the Bears were one of five teams to add a starting quarterback via free agency or trade during the 2020 offseason. Four others used first-round picks to grab a quarterback of the future, while the Philadelphia Eagles swung in Round 2 for Jalen Hurts.
The Buccaneers, however, were the only ones lucky enough to land Brady, almost instantly changing the direction of the entire organization.
Not long after Brady signed his $50 million contract — and handed that all-important paperwork to Gellerman — questions as to why he chose the Buccaneers intensified. The COVID-19 pandemic turned everything so completely upside down that Brady's introductory news conference was done via teleconference.
When he was asked for specifics on what drew him to Tampa, his answers remained vague.
"I don't want to get into every process of the decision I was making," he said then. "But there are a lot of things that really were intriguing about the organization and the players and the coaches. And the willingness of everyone to try to accomplish what the goal of playing football is, which is to win. I'm going to try to do everything I can in my position and with what I'm responsible for to make it happen."
Certainly, Brady looked closely at the Buccaneers' offensive ammunition - most notably receivers Mike Evans and Chris Godwin plus tight ends Cameron Brate and O.J. Howard and running back Ronald Jones — and felt intrigued. He knew, too, that he would have a chance, in his words, to "be seen and heard" with input on ways to fortify the roster.
Brady also appreciated Bruce Arians' long and successful track record working with quarterbacks plus his fearless "no risk it, no biscuit" mindset as an offensive strategist.
"I've watched this offense over a long period of time with a lot of different quarterbacks that have a lot of success," Brady said. "It's a great offense for the quarterbacks. It's a great offense for the receivers, for the tight ends, for the running backs."
Those aren't things Brady would have been able to express about the Bears.
Soon after, in a lengthy article for The Players' Tribune, he labeled his fresh start in Tampa as "a great opportunity, a great chance and a great challenge."
"I'm excited," he wrote. "Most of all, I'm motivated. I want to deliver for my new team, my new coaches and my new teammates. I don't want to let anyone down. I'm going to give it everything I've got."
Even at age 42, Brady seemed rejuvenated by his fresh start, fully engaged on a new mission with a new team.
"I have things to prove to myself," he wrote. "The only way is through. If I don't go for it, I'll never know what I could have accomplished. Wanting to do something is different from actually doing it. If I stood at the bottom of a mountain and told myself I could scale the highest peak but then didn't do anything about it, what's the point of that?"
Brady and the Buccaneers will play host to the Bears on Sunday at Raymond James Stadium. The forecast calls for possible afternoon showers and a Bucs runaway. Brady is 5-1 against the Bears and has brought his fair share of thunder too.
In 2014, for example, the Patriots scored three touchdowns in a 57-second span late in the first half during a 51-23 beatdown at Gillette Stadium. Four years earlier, inside a Soldier Field snow globe, Brady shook things up to the tune of 369 yards and two touchdowns, including a 59-yard strike to Deion Branch on the final play of the first half.
Brady, of course, isn't perfect. Last season, for the first time in his career, he lost to the Bears. On a prime-time stage. The Buccaneers faltered on that Thursday night, falling 20-19 and getting shooed out of Soldier Field after their star quarterback had an uncharacteristic brain fart on his closing drive, thinking his fourth-and-6 incompletion to Brate in the final minute had come on third down.
As the Bears defense celebrated an exhilarating upset, Brady stood perplexed, unknowingly turning himself into an "Oops!" GIF by flashing four fingers and wondering why he wasn't getting another down.
He was curt after the game in discussing that mental mistake but admitted eight months later on — of all places — his TikTok feed that he blew it. Commenting on a still photograph of himself with those four fingers raised, Brady said, "Fourth quarter, last chance in Chicago. I thought it was the second-to-last chance in Chicago. But apparently not. I don't think I've ever been as confused as I am in this moment right here. Look at that face."
Everyone remembers that slip-up, in part because that kind of Brady blunder is so rare. And you can bet Brady remembers it well, perhaps plotting the most vicious way to make up for that in Sunday's rematch.
Who knows? Brady is enough of a ruthless competitor that he might try to throw four first-half touchdown passes in order to wiggle his fingers for the Bears again. Maybe, if the Bucs win big as everyone expects, Brady will even race to find Bears third-string quarterback Foles for the postgame handshake he so notoriously ditched out on a year ago.
A numbers game
Hey, when you're Thomas Edward Patrick Brady Jr., it often can be easy to lose count. So many achievements to keep track of. Too many mind-boggling numbers to compute.
Since the Bears last won a playoff game, for example, Brady has won 20 of them, including four more Super Bowl rings.
That's worth repeating. Since the Bears last won in the postseason in January 2011, Brady has 20 playoff victories and four Super Bowl championships.
In fact, if you took only Brady's career postseason statistics and mixed them into the Bears' all-time passing records, his 12,449 yards and 83 touchdown passes would rank third - behind only Jay Cutler (23,443 yards and 154 TDs) and Sid Luckman (14,686 and 137).
As has been well-documented, the Bears never have had a 4,000-yard passer. Brady has reached that benchmark a dozen times in his 21 seasons and undoubtedly will blow past that mark this season.
Erik Kramer in 1995 is the Bears' single-season leader in touchdown passes with 29. Brady has topped that eight times and is on pace to throw 48 this season. At age 44.
Two weeks ago, Brady threw three touchdown passes in the first half of the Bucs' 45-17 thrashing of the Miami Dolphins, then added two more in the second half. The Bears have three touchdown passes. Total. This entire season.
In six games, the Buccaneers are averaging 32.5 points. The Bears, meanwhile, have scored more than 32 just nine times in the last eight seasons.
So, yes, counting along with Brady can sometimes get a little dicey.
The fork in the road
Around the NFL, there's a fascination with what Brady has accomplished in Tampa so quickly, almost single-handedly transforming the Buccaneers from afterthoughts into champions.
No one was surprised Brady found his footing and played at a high level. He had been doing that for two decades. But that he was able to fuel an entire franchise and convert his efforts into a Super Bowl championship in Year 1 for a team that hadn't won a playoff game since 2002 was beyond remarkable.
Because it wasn't just Year 1. It was a year in which disruptions related to COVID-19 eliminated the entire offseason program, canceling organized team activities and minicamp practices. It was a year in which full-speed, on-field time at training camp was sliced in half. It was a year in which — other than tight end Rob Gronkowski — Brady had to meet dozens of new teammates and develop chemistry with them.
The Buccaneers were slow to get rolling and hit their roughest patch in November, losing three times in four games. But they regrouped, won their final four regular-season games and then rolled to the Lombardi Trophy as the No. 5 seed in the NFC.
As usual, another variation of the "What if?" game circulated through Chicago, prompting daydreams of what Brady might have achieved had he opted to become a Bear instead.
While Brady was fueling up for a Super Bowl run with an offense that was picking up steam late in 2020, the Bears' quarterback situation was circling the drain. Again. A desperate attempt to give Trubisky his one last shot to emerge as a franchise quarterback failed in 2020, and the team's installed safety net broke right beneath it.
Foles' performance failures coupled with a mid-November hip injury persuaded Nagy to turn back to Trubisky for the final six games of the regular season. And when the seventh-seeded, 8-8 Bears whimpered out of the playoffs with a wild-card-round loss to the New Orleans Saints, Nagy and Pace agreed to start over at the most important position on their roster, sending Trubisky into free agency and later demoting Foles to third string.
In came Andy Dalton, a $10 million free-agency signing that was not well-received in Chicago. A little more than a month later, Pace traded up to draft Fields with the 11th pick.
On his SiriusXM show "Let's Go!" this week, the normally measured Brady didn't hesitate to throw some additional shade at the Bears. On Sunday, as the whole world saw, Aaron Rodgers led the Packers to a 24-14 win and savagely reminded Bears fans he had their number.
"All my (bleeping) life!" Rodgers shouted into the stands after scoring a fourth-quarter touchdown. "I own you! I still own you!"
Brady was among those amused, sarcastically congratulating Rodgers on his show.
"Not only is he a great quarterback," Brady cracked, "but I guess he's now a shareholder of the Bears. I saw a clip of him really enthusiastically telling the crowd how happy he is to own Soldier Field.
"That's really great stuff. He owns (a minority stake in) the (Milwaukee) Bucks now. Part-owner of Soldier Field. So he has a great career beyond football."
Normally very measured with his words, Brady clearly didn't mind supplying the tenants at Halas Hall with some poignant bulletin-board material for the week. It felt calculated, a warning of sorts to the Bears for what might await Sunday.
Brady remains at the controls of one of the league's most explosive offenses and continues to fuel the Bucs' push to earn the NFC's top seed. Through six games, he has thrown 17 touchdown passes while averaging 344 passing yards per game.
The Bears, meanwhile, are accelerating Fields' development while trying to properly connect the jumper cables to awaken a passing attack that is averaging a league-worst 117.2 yards per game.
The two organizations are clearly in very different places. On Sunday, they will take their swings at one another. History is still being written.
On that Wednesday evening 19 months ago, when Brady signed his new deal in his kitchen, he essentially agreed to load the entire Buccaneers organization onto his rocket ship. Then he handed the papers back to Gellerman, who promptly finished his conversation with Brady's son, Jack, and headed back toward home.
Gellerman stopped first at a FedEx store near his apartment building, scanned the landmark contract and overnighted the originals to One Buccaneers Place in Tampa.
A little more than 11 months later, Brady was the Super Bowl MVP, and everyone affiliated with the Buccaneers was euphoric.
Gellerman couldn't help but laugh to himself.
"I had to feel like I was a little part of that whole thing, right?" he quipped. "I'm still waiting for my ring."
Maybe another pop-in at Brady's place is in order. He probably has a spare sitting around.