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The Education of a Young NFL Front Office Phenom

Andrew Berry’s rapid ascent to becoming the youngest GM in the NFL is no surprise to anyone who’s known him. The Browns’ makeover wouldn’t have been possible without him.

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Andrew Berry starts his day every morning with a CrossFit class at around 6 a.m. The regulars know who he is—the general manager of the first Browns team to win a playoff game in 26 years—and they do not care. “I don’t know how much it really matters in CrossFit when you’re all gasping for air,” he tells me.

“Nobody cares about Baker Mayfield’s extension there?” I asked him at a Browns training camp practice last month.

“Nobody cares about that when you’re doing heavy thrusters,” he said.

Most people around Cleveland, and in the NFL, do care about Berry. To say he is one of the best young executives in the sport is to obscure the fact that he is one of the best executives of any age in football. He is six years younger than any other GM in the league. When he was hired in January 2020, he had a solid decade on every one of his brethren. He is also much better at his job than many of them.

Let’s start in 2009, when Berry’s Harvard football coach, Tim Murphy, told The Harvard Crimson, “For my two cents, he’ll be running an NFL team in 15 years. At 37 years old, he’ll be running an NFL franchise. I have no question.” Murphy was way off. It took Berry only 10 years. Murphy doesn’t remember saying this out loud, but he remembers thinking about it often. Berry’s story is of a front office prospect who delivered, like the Trevor Lawrence of front office work, someone who’s been talked up for years and did all the right things during every step of his development. There is no guarantee that Berry will win a Super Bowl or deliver the Browns to consistent contention or anything else. What Berry has delivered is the general consensus that he’s awesome at his job—in his second year running the team, that’s pretty good.

The NFL part of this story starts in September 2008, when Tom Telesco, then the Colts’ director of player personnel, stopped by a Harvard–Holy Cross game while on a Boston College scouting trip. There was a story about Berry in the game-day program and Telesco wrote his name down. “I thought, ‘These are the type of guys we need working in football,’” Telesco, now a top GM in his own right with the Chargers, told me last week.

Berry was, Murphy told me, arguably the best defensive back in Harvard history, even if he was not a true NFL prospect. “Everything just came so easy to him. Not in terms of him not giving great effort—he always gave incredible effort—but he was just so naturally [gifted]. He was our strongest student. To my knowledge, the first and only Harvard student-athlete in history to attain an undergraduate degree in economics and a master’s degree in computer science as a four-year varsity athlete. If he was bigger, he would have had a shot to be an NFL corner.”

The first player Berry ever scouted was himself. “I was a one double-A press-and-run corner,” he says. “I was pretty self-aware that I was not going to go in the first round, to put it kindly. I had a pretty reasonable expectation that my best-case scenario is to sign a free-agent deal. My expectations were tempered, but my desire and work ethic was still there.”

He made it as far as rookie minicamp with Washington and his playing career was over, leaving him with two options. Murphy thought Berry was probably the top Wall Street recruit in the country. Telesco told him that if he wanted to get into football, he should do so that year. “These entry-level jobs don’t pay much,” Telesco explained, and once Berry got married and had a family, it would be harder to chase his NFL dream with lower-paying jobs. On the flip side, if he took the football job and it didn’t work out, Wall Street would still be there.

“I vividly remember saying, ‘I’m a little concerned. You can write your own ticket. The path to where you might want to get in the NFL is just so unpredictable,’” Murphy said. He told Berry that if this is what he wanted, he’d succeed at it. “But I was like, ‘Do you know what you’re passing up?’ And he said, ‘Yeah, I do, Coach, but I love football.’”

Berry, obviously, took the football job after college, joining the Colts as a scouting assistant. He said it was an intersection of all of his interests—strategic, athletic, and academic. He did not self-promote, Telesco said, instead letting his work promote himself. This is not altogether common. “He did whatever you asked him to and put all of his work into that. Not every guy who comes into the league is like that. Everyone’s always trying to move up the ladder as fast as they can and lose focus on what their current job is,” Telesco said.

Berry rose up the ladder faster than almost anyone in league history anyway. He asked what Telesco called “second-level” questions, indicating he always understood the big picture. He picked the brains of his bosses in Indianapolis, including Telesco, Colts GM Bill Polian, and Polian’s replacement, Ryan Grigson. He picked things up at his other stops, from Sashi Brown and John Dorsey in Cleveland and Howie Roseman in Philadelphia. There is a chicken-and-egg aspect to his rapid ascent: Berry said he became a GM at such a young age because these executives opened their world to him—Grigson asked him to help with contract work, for instance, and other GMs gave him different responsibilities. But most of the executives I talked to said they opened their world to Berry because he was good at everything and could handle it.

The questions Berry asked in meetings and while sitting around the desks of the guys he worked for led to his current role overseeing a buzzy AFC contender, and now we’re talking about the team he’s built in the shade in suburban Ohio, as the team walks into the locker room.

The Browns have, on paper, plugged some holes in their roster for the second straight season, signing defensive backs Troy Hill and John Johnson III, as well as defensive end Jadeveon Clowney. Oddsmakers have made them the fourth-highest favorite to win the AFC. Berry has massive decisions to make going forward: Quarterback Baker Mayfield is entering his fourth season, meaning he has just next season’s fifth-year option remaining on his current contract. Berry told me last season he “pushes back” on the narrative that a team becomes hamstrung once it signs a quarterback to the kind of mega contract Mayfield may eventually command.

Berry’s journey typifies modern football and the people who will lead it. Being the GM of a football team in 2021 is far different than it was even 20 years ago: It involves analytics, near-constant leaps in technology, and much more sophisticated player evaluation. Berry’s philosophy starts with the quarterback position.

“Quarterback is the most important position in sports,” he said. “And so for me, as I came up under Bill [Polian] and pretty much every stop, this was the belief, and certainly my last stop in Philly: It’s make sure we do everything to support that position first and foremost. Because you can do a lot of really great things, but if that position isn’t solved and the environment isn’t conducive to that player having success, then you’re really kind of stuck in neutral,” Berry said. “So we’re doing everything that we can do to support the quarterback, because ultimately that’s the position that’s going to drive you. Then, once we get that environment settled, whether it’s on-field or off-field, then, really, kind of transition into [other] priorities.”

I asked Berry how the Browns were able to significantly improve last season when COVID-19 restrictions made it so hard for teams to do so. In short, I wanted to know how he built a culture in a year when you could barely meet in person, when every meeting happened on Zoom, and it was hard to introduce yourself to anyone, let alone to an entire organization.

“I think it’s just being yourself,” he said. “I think a lot of people get into organizations or positions and they change who they are. And I think [Browns head coach Kevin Stefanski] and I took the approach that we’re disciplined but in a pretty laid-back way. We wanted to establish a culture of calm,” Berry said.

The “culture of calm” part of his response is important. Murphy said that he used to talk to his staff about Berry having a “preternatural calm to him.” Very few general managers have more big decisions to make with a talented young roster than he does. Aside from Mayfield’s potential extension, the team recently extended Nick Chubb, and has a stable of high-priced players, including Odell Beckham Jr. and Myles Garrett; the Browns rank first in the NFL in the amount they are spending on “high” salaries (which Over the Cap calculates as between $7.3 million and $15.8 million). They also, crucially, rank third in money spent on rookie contracts, which means they can afford to carry expensive players. But valuable rookie contracts eventually lead to veteran deals, making it even more important to have a smart GM tending to the team’s business. In a potentially chaotic environment, there is a culture of calm in Cleveland. Berry said he’s never been a big social media guy—he follows NFL news on Twitter just for transaction information. He guessed he’s posted on social media fewer than 10 times since college.

“The world could be ending and Andrew would be quietly figuring out a way to handle it,” Murphy said. “It’s just who he is. That’s why there’s so many accolades in his history. He’s unflappable.”

Which could explain, in part, why Berry is the perfect person to fill the gaps in the Browns’ roster and improve the team every year, especially at an organization that’s had its fair share of chaos. It could also be why, when I asked Berry about the team’s current roster, he refused to get ahead of himself even a little bit—he won’t even talk about any roster move that excites him.

At an awards dinner when Berry was in college, Murphy told Andrew’s mother that her son was one of the most amazing kids he’d ever been around. His mother said, “My Andrew? Have you seen his room?”

“So you see,” Murphy said, “where he gets his humility.”

“I’ll be honest,” Roseman said. “There was no job interview.”

Roseman hired Berry to join the Eagles’ front office in 2019 and, well, that’s the answer I got when I asked him what that meeting was like.

Roseman had heard so much about Berry from Grigson that Roseman had long wanted to recruit Berry if he were ever available. Berry has raved about his one year in Philadelphia, saying earlier this year that Roseman is the best GM in football. Last year, Berry outlined the things he learned from Roseman: aggressiveness, getting to know your locker room, and getting the right mix of people on the roster.

“I appreciate Andrew talking about how he liked his time here, but let’s be totally honest, I’m better for being around him and having him in Philly,” Roseman said.

Roseman said he taught Berry, “You have to be OK with making some mistakes, and that means you’re going to be OK with the fact that sometimes when you’re aggressive, it doesn’t work out,” Roseman said. “But unless you’re aggressive—and really this comes from the [early 2000s] Philadelphia Eagles when I was here, and Jeffrey [Lurie] and Joe [Banner] and coach [Andy] Reid—with greatness is gonna come risk. And I think that was important for me to learn early on, and we’re not going to be scared here, and that means that it’s not always going to be popular. It’s not always going to look right. But that’s probably the reason the confetti fell on our head once.”

Modern front office work is different, Roseman said, and he wanted to give Berry exposure to all of it. “You can’t just sit in your office and watch tape,” Roseman said. “You got to deal with the trainer, you got to deal with the equipment guy, the video guy, the security guy, you got to talk to the head coach, you got to talk to ownership, you got to manage your staff. And so I think at the end of the day, it’s resource allocation—the cap and the contracts, the analytics group. So I think you talk about, ‘How are you going to be prepared for that?’” In 2015, Chip Kelly took power in Philadelphia and Roseman was briefly sidelined as the Eagles’ personnel head. He said he spent that year talking to front office members in basketball, baseball, soccer, and hockey, and he noticed that those executives often had more diverse résumés than those in football. “You’re talking about billion-dollar companies and payrolls that are approaching $200 million on the player side, and you have to hire everyone. So it’s a little bit more of a CEO than has been traditionally thought of, especially as the NFL grows, which is good for everyone.”

Roseman tasked Berry with a wide array of responsibilities: player development, coordinating with the medical and performance staff, helping with the cap and contracts, and talking about big-picture issues.

“Andrew is so inquisitive and so smart that there will be times you’re like, ‘Can we get to this question after the waiver wire at 4 o’clock, dude?’

“He was always asking questions. He would say, ‘Tell me why. And tell me how you thought about this,’” Roseman said. “And I told him, the thing that I’m most proud of is just watching his actions. He knows I’m obsessed with the O-line and D-line, and he got to Cleveland, and it was like an O-line and D-line fest. I was like, ‘I’m so proud of you, bro.’”

“I’ve gotten into, I guess, a little bit of a board game fetish,” Berry said.

While he was at Harvard, Berry’s brother told him about a game called Settlers of Catan. Berry stopped at a vintage board game store in Harvard Square. “I’d never seen anything like it. It was the first German board game I’d been exposed to. I’d never seen a game with this type of mechanics.” The night before a big game, Berry said he was on “dorm arrest,” unable to leave his room. His roommate and his roommate’s girlfriend wanted to play Catan. “Really, they probably played out of pity,” Berry said. Soon his whole floor was hooked. He’s moved on to other games—Berry and his wife now play Dominion, which he calls a “a deck management game.” He said that any board game recommendation will at least be considered.

“With American board games, like Monopoly, turn-based board games to some degree become boring, because we can just predict the outcomes,” he said. “Whereas with Settlers, I thought, the element of randomness, and the variety of strategies that you could have to win the game, that’s what was appealing. So it was both a new game every time, and a new challenge every time and different strategies can actually win.”

This answer sounds eerily similar to what he said when I asked him what his favorite part of football was. “The roster strategy,” he said quickly. “The roster-building portion in general. It’s my favorite part of the job. I feel like constructing a team, building a team with all the different groups and all the different people in there.”

In doing that in Cleveland, Berry has completed the work of two of his former bosses, Brown and Dorsey, both of whom were fired within three years on the job. Their work cannot be erased from this roster, despite an almost unbelievable amount of stops and starts on the assembly line. Chubb was selected with a pick acquired when the Browns took on Brock Osweiler’s contract via a trade with the Texans in 2017. Cornerback Denzel Ward was taken in 2018 with the fourth pick, which came from Houston the previous year in the Texans’ trade up to acquire Deshaun Watson. Mayfield and Myles Garrett were taken with no. 1 picks by Dorsey and Brown, who were in position to do so because the Browns were in the middle of a significant roster teardown at the time. I do not want to relitigate this era, but it is important to mention two things: The first is that you cannot tell the story of the 2021 Browns without talking about this period in franchise history; the second is that Berry was the one who finally delivered good football on the field.

I wanted to delve into Berry’s mind. Browns coach Kevin Stefanski first met him in 2013 at the Senior Bowl—they developed a relationship and kept texting and talking through the years. Stefanski doubts anyone is more prepared in the draft and free agency (not letting the other end of the mutual-admiration society down, Berry said there is at least one person who is: Stefanski himself). Stefanski said the thing to remember about Berry is that he was a genuinely good player, much better than Stefanski, who played defensive back at Penn. “He was actually good,” he said. “So he has this football acumen, having played really good football for Harvard, and he has this background where he’s brilliant and smart. So he’s like a nice blend of the football guy, the guy that understands the nuances of contracts, etcetera, etcetera. He’s pragmatic.”

“I wish he was smarter,” Stefanski joked. “That’s the damn shame. Couldn’t get into Penn, had to settle for Harvard.” The topic turned to his age. Stefanski, the reigning NFL Coach of the Year, is only 39, which is young by league standards but puts him five years older than Berry. “It’s really annoying,” he joked.

I asked Berry to outline his day. He believes in routine. He wakes up at 5:40 a.m. every day, listens to a sermon on the way to his aforementioned CrossFit class, then meets with the Browns’ scouting coordinator at 8:30. He does prep work the night before because he believes that once the day gets started in football, very few adjustments can be made. “Once the train gets moving it’s hard to change the direction of the tracks,” he said. “You need proper balance, you can always do more work, but if you’re not in the right physical mindset or mental mindset, the quality isn’t going to be very good.”

The work has been good. It continues Sunday against the Kansas City Chiefs. It also continues tomorrow at CrossFit.

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