As the losses mounted, at a rate that would strain any person’s patience or capacity for self-effacing humor, Andrew Berry finally understood the measure of his boss’ character.
Berry was vice president of player personnel for the Cleveland Browns, and he worked for Sashi Brown, an unorthodox football executive doing his best to tear a woeful organization down and build it back up. The teams Brown constructed in 2016 and 2017 won exactly one game in 32 tries, about as bad as it gets by the NFL’s unforgiving calculus.
As the horror show deepened and exasperated fans sharpened their pitchforks, Berry, the Browns’ general manager today, never saw Brown lose faith in his plan or turn cold to the people around him. “He is very secure in his skin,” he said. “He was the same guy every day, a steady hand to guide the ship when the ship was going through very turbulent waters. … That consistency was something that all of us as younger executives took with us, something that we really learned from Sashi.”
There are critics who would reduce Brown, the Baltimore Ravens’ new team president, to the 1-31 record he compiled as Cleveland’s top football decision-maker. But those who have worked closely with him say he’s a man of exceptional intelligence and empathy whose contributions to his previous NFL employer were misunderstood and underestimated. Though Brown will not run the football operation in Baltimore, former colleagues predict he will thrive as owner Steve Bisciotti’s right-hand man and as one of the highest ranking Black executives in a league that has faced sharp criticism for its sluggish record in promoting minorities.
“You could drop him into any company out there and he would much sooner rather than later be in a senior position, with a lot of people hanging on his every word,” Browns chief strategy officer Paul DePodesta said. “He’ll be a great face for that organization. I think the Ravens have always been a tremendous organization, and this is just another really, really smart move by them.”
Brown has stepped in for Dick Cass, an early professional mentor for him and the understated figure who spent 18 years putting his imprint on every nonfootball aspect of the Ravens, from stadium upgrades to the organization’s handling of the coronavirus pandemic. Brown has spent the last two months gaining familiarity with every person at the team’s headquarters in Owings Mills, and his style — listen first, ask incisive questions, think carefully before you speak, take the long view — reminds co-workers of Cass.
“I think he’s very similar to him,” Bisciotti said. “His intelligence and the humility remind me of a young Dick. Anybody that is really smart, you really fall in love with them when they don’t try and convince you that they’re smart.”
Brown’s personal touch is a theme, praised by colleagues from each of his previous stops. Monica Dixon worked closely with him at Monumental Basketball, the parent company of the NBA’s Washington Wizards and the WNBA’s Washington Mystics, where he landed after he was fired by the Browns. She recalled how, after a difficult meeting, Brown would always find time to call later in the day.
“He would just say, ‘So, how you doing?’” said Dixon, a former deputy chief of staff to Vice President Al Gore. “He wouldn’t even necessarily bring up the specific meeting or whatever hard thing you were both dealing with. He just checked in.”
‘There are lots of ways to be in sports’
Brown, 46, grew up in Connecticut and Massachusetts as the middle child of a pair of college professors. His mother, Cheryl, recalled the unusual range of cultures and ideas that shaped her children as they spent their early years in Middletown, Connecticut, where their father, Leonard, was studying for a doctorate in ethnomusicology at Wesleyan University.
“It was full of people from lots of different cultures and lots of different races who mingled together in ways that you did not see a lot in the 1970s,” she said.
All three of her children were bright (Brown’s brother, Omrao, became an engineer and jazz club owner and his sister, Samira, a pediatrician), but she noticed that Sashi (an East Indian word for “moon”) was a natural observer who worried about the day-to-day injustices he watched classmates suffer. The family would discuss these examples at home, with Leonard lending the perspective he had learned growing up in segregated Kentucky.
“I think they were very realistic,” Sashi Brown said. “Their experience growing up was something they did not beat into us, but it was something we were very conscious of … the importance of the opportunities that we have and not facing some of the challenges that they did.”
“We were very much advocates of the world being a more just place,” Cheryl said. “There are a lot of heroes in African American life, and we exposed our kids. They had books about them. They knew about race struggles from a very young age, and as they saw things, we talked to them about: ‘What are the strategies you could use to address this?’”
Brown and his wife, Paige, would go on to name their children (they have four, ranging from 4 months to 10 years old) after great Black activists and artists such as Paul Robeson, Ralph Ellison and Zora Neale Hurston.
At the same time, sports tugged at Brown’s soul. His paternal grandfather had coached basketball at Kentucky State University, and his father, who died in 2019, handed down that familial passion. The Browns watched Big East basketball in its heyday, as the University of Connecticut rose to compete against the likes of Syracuse and Georgetown, led by the great Black coach John Thompson.
When it came to playing, Brown joked that he was the “runt,” a slight figure next to his 6-foot-4 dad and 6-foot-4 older brother. Organized football was never in the cards, but he did play basketball, sharing a high school backcourt with future ESPN writer Mike Reiss.
Cheryl knew her son was not going to play in the NBA, but she saw a poster at an educational conference that depicted a young Black athlete who would eventually transcend the court and own a team. She brought it home and mounted it on the wall in Sashi’s room.
“It was planting the idea that there are lots of ways to be in sports,” she said.
‘He laid down a lot of the foundation’
Brown headed south for college at Virginia’s Hampton University, which had an excellent broadcast journalism program “that really ignited me academically.” If he could not play in the games, perhaps he could call them on ESPN, where he interned as a production assistant. He loved that work, but not the starting salaries in sports media, so he opted for Harvard law school, hardly a shabby fallback. There, he gravitated toward corporate law, always keeping an eye out for potential paths into sports.
He found one in the Washington firm of Wilmer Cutler & Pickering, where Cass was a partner and had worked on the sales of several NFL teams.
From there, Brown moved to his first NFL job, as general counsel for the Jacksonville Jaguars, in 2005. He jumped to the Browns in 2013, working on salary cap management and other administrative matters until owner Jimmy Haslam named him executive vice president of football operations in January 2016. The move raised eyebrows because Brown was a lawyer who knew far more about contract language than he did about scouting middle linebackers, but Haslam believed his strategic thinking would help pull the team out of a decadelong losing malaise. He paired Brown with DePodesta, a key character in the bestselling book “Moneyball,” which chronicled the Oakland Athletics’ drive to conquer baseball with outside-the-box thinking and a small pocketbook.
“He was very much a part of the decision [to go there] for me,” DePodesta said. “I think he sees certain things that maybe not everyone else sees. … I don’t think there was a desire to be an iconoclast just to do it. I think it was all in the name of wanting to do something special and not being afraid of having to make some tough decisions.”
They agreed the Browns might need to get worse before they got better, and they were prepared to endure many painful Sundays while the process played out. But the losing proved too frequent for Haslam, and he fired Brown with a few weeks to go in the 2017 season.
Brown does not have much interest in rehashing the end of his tenure with the Browns. “I think probably enough has been written about Cleveland and my days there, and it’s time … I’ve certainly turned the page,” he said at his introductory news conference with the Ravens. “I think it’s plenty time that we move on from that.”
It was easy to lampoon Brown’s front office as a bunch of Harvard pointy heads — Berry and DePodesta are also Crimson alumni — whose cherished analyses held no water in the big, mean NFL.
But Berry and DePodesta, who are running the team now, said the Browns could not have made the playoffs in 2020 without Brown’s foresight in stockpiling draft picks and clearing salary cap room.
“One of the things that’s really too bad is that he didn’t ultimately get to enjoy the successes that we have had,” DePodesta said. “Because he’s responsible for a lot of it. He laid down a lot of the foundation, which was awfully, awfully difficult at the time.”
Beyond professional respect, Berry and DePodesta’s enduring affection for Brown is clear. Both refer to him as “Sash.” Their spouses and children are friendly and they’ve dined at one another’s homes.
“He really treated me like family. I almost feel like he’s a big brother,” said Berry, who before Harvard starred as quarterback at Bel Air High School in Harford County.
Now that he’s back in the NFL, Brown has taken a quiet approach to his first few months with the Ravens, unsurprising from someone who considers Cass and former Ravens general manager Ozzie Newsome his role models. But he will have a powerful hand in the direction of the franchise, including plans to spend the Ravens’ half of $1.2 billion the Maryland General Assembly approved for updates to M&T Bank Stadium and Camden Yards. He spoke of “the opportunity this platform provides to be meaningful to the world around us” while maintaining a focus on winning games. He recently spent a day taking a neighborhood-by-neighborhood tour of Baltimore.
Beyond the particulars of his job, Brown will stand out as a Black executive in a Black city in the nation’s most popular sports league, a realm long dominated by white men.
“People who are observing the sport, they see seven Black general managers, two Black team presidents; I do think that stuff matters because we do want our leaders to be aspirational [figures],” said Berry, one of the league’s Black general managers. “I also think it’s important because it leads to better business across the industry. And that’s not just Black or white. That’s gender. That’s different backgrounds in terms of expertise. I think all that stuff matters.”
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