Brown pushed play on the machine and heard one of his prospective bosses: Call us back, and don’t get on the train. “That doesn’t sound good,” Brown thought. It wasn’t: The NBA’s team owners were locking out the players. The labor dispute meant his internship offer had vanished.
The moment redirected Brown’s career at the beginning, starting him on a trajectory that made him a rare figure among North American sports executives. Even in an era when the people in front offices are just as likely to come equipped with an alphabet soup of degrees as a professional playing career, Brown’s résumé stands out.
The son of college professors from outside Boston, Brown has a law degree from Harvard. He has been lead counsel and a general manager in the NFL and a lead executive in the NBA, earning admirers and detractors along the way. This year, he left the Washington Wizards’ front office and became president of the Baltimore Ravens, making Brown the top executive for one of the most stable franchises in America’s most popular league.
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None of it was planned. Brown’s career path, and that he ended up working in sports at all, derived from his search for new opportunities and his belief that people drift toward their passions.
“I feel like I’ve rolled snake eyes in some ways,” Brown said. “It’s just not what you want to bet on.”
When Baltimore named Brown to replace Dick Cass, the Ravens’ longtime team president, in February, Brown became the second Black man to hold the title in the NFL. At his introductory news conference, Brown called that “a big, complicated topic.” As Brown praised the Ravens’ record of diverse hiring, he called for the NFL to provide more opportunities.
“The first thing I would say is, we just shouldn’t be here,” he said. “We should not be here in 2022 and being only the second African American. We still haven’t had a woman who’s at this point ascended, although I think there’s some arguments there’s been one or two who haven’t had exactly that title. We need to do better. Wall Street needs to do better. And the NFL is no different. ”
Brown’s parents – Cheryl, an education teacher, and Leonard, an ethnomusicologist – made it a point each night to eat dinner with their three children and discuss their days. They would tell them, “No matter what people tell you or expect of you, we expect greatness, and you are capable of greatness.”
Cheryl sensed in Sashi a keen sense of fairness. Kids from the one housing project in town attended his elementary school, and he would alert his mother when those friends received different treatment from teachers. Leonard exposed their children to injustice and the people who fought against it. “From a very early age, he saw models of that,” Cheryl said. “That braces you for the world you’re about to face growing up. And I think he was somebody who was poised to do that. ”
As Brown ascended, first as a lawyer and then in front offices, he would often be surrounded by a few non-White faces. It placed on him a hidden burden.
“I don’t think any of us can escape that when there’s not a fairness in opportunity and one of us or some of us have an opportunity,” Cheryl said. “There’s no question that you feel you’re going to be judged.”
Brown’s first love was basketball. His paternal grandfather coached the sport at Kentucky State University, a historically Black school. Brown’s father passed basketball on to his children. Sashi, the middle child, played point guard. He loved the teamwork and how a team could bond a community.
“There’s just so few things that cross ethnic, religious, national, gender – all these walls that we put up around ourselves as we tend to be tribal,” Brown said. “I think music and sports are the things that really bring people together.”
Freddye Davy, the head of the honors college at Hampton, pressed Brown to pursue law school. He resisted, pointing at the job he had lined up. When the 1998 NBA lockout canceled the internship, Davy had another chance. Harvard Law School accepted Brown, and after graduation he joined high-powered Washington law firm WilmerHale, working on a team led by Cass that specialized in sports litigation.
He worked with the group that executed the contract that made Steve Bisciotti the Ravens’ full-blown owner in 2004. Brown was in the downtown Baltimore office when the deal closed. Two weeks later, Cass announced to his WilmerHale colleagues that Bisciotti had hired him away to be the Ravens’ president.
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By the early 2000s, the NFL was becoming the financial colossus it is today. National revenue and media rights skyrocketed. The business grew more complex. High-powered lawyers versed in the league were suddenly commodities. The Jacksonville Jaguars poached Brown and made him their lead counsel.
After a few years, Brown started working on Jacksonville’s football side, assisting with salary cap management and contract negotiations. As the Cleveland Browns revamped their front office in 2012 after truck stop magnate Jimmy Haslam purchased the team, they sought executives who had worked in business and football. “I was probably one of the few people who did a little bit of both,” Brown said.
The Browns named Brown an executive vice president, and then in 2016, in a bid to rethink the front office after years of dismal performance, Haslam promoted Brown to general manager. An executive who had spent his career behind the scenes became the face of a foundering franchise in the midst of an experiment.
“I had a long talk with my family prior to accepting and had a long talk with the ownership about what we were going to do and how we were going to do it and what that would mean,” Brown said.
From the start, Brown had a problem. “He just couldn’t manage Jimmy,” said one of Brown’s Cleveland colleagues, who spoke on the condition of anonymity to discuss their former employer candidly.
Haslam’s ownership style made it impracticable for an executive to implement his preferred vision. Haslam would seek opinions from a wide array of people in the organization, then do what he wanted to do in the first place. “When you’re around [Haslam], you think, ‘This guy is really listening to me,’ ”the former Browns employee said. “And then he goes and does the complete opposite.”
Haslam’s heavy influence derailed perhaps the most important decision Brown would make. As the Browns set out on their rebuild, hiring a head coach who shared their philosophy and understood the long-term outlook would be paramount. Haslam grew convinced about hiring Hue Jackson, a longtime NFL assistant and head coach. Brown and the front office viewed Jackson as the wrong fit, according to multiple people familiar with the situation.
“Sashi would not have hired Hue,” the former colleague said.
Even among Cleveland staffers, there is debate about Brown’s role in Jackson’s hiring. Some believe Haslam was headstrong and wouldn’t be persuaded by his general manager. Some believe Brown didn’t do enough as a leader, perhaps out of inexperience and lack of political capital early in his tenure, to prevent what many saw as an oncoming disaster.
“If you felt that strongly about it,” the former Browns employee said, “you got to stand in front of the train.”
Jackson’s tenure was disastrous. The Browns won one game in two years, which included the second 0-16 season in NFL history. The Browns anticipated they would sink to the bottom of the league in order to rebuild, but nobody expected how ugly it would get. Brown became a target of the fan base’s ire. Some colleagues questioned his internal approach, two former Browns executives said. In their view, he would prioritize personal credit and blame over organizational success.
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“I could see it affecting him,” one colleague said. “There was a weight on him that was unlike years prior. I’m not sure he ever shook that. ”
In December 2017, Cleveland fired Brown. The Browns reached the divisional playoff round in 2020 and have become a team annually projected as a playoff contender, if still a franchise mired in controversy and underachievement. Much of the Browns’ talent was acquired with resources – draft choices and salary cap space – acquired during Brown’s tenure.
“In some ways, he was kicked off the roller coaster midway through the ride,” one of the former colleagues said. “I’m not sure you were able to fully see what he was able to do as a GM.”
Brown maintains he has no regrets about his Cleveland tenure.
“We knew what we were inheriting needed a real foundational fix,” Brown said. “We made it harder on ourselves by not being aligned. But we knew it was going to be hard no matter what. I knew what I was getting myself into. As an adult and a human being, you know there’s some challenges out there that aren’t always paved. We were going into some rough and choppy waters. I don’t regret it. There’s aspects of it I think were disappointing from a personal level. But I know what we accomplished there. I know a lot of people still there, the talent we brought there, the character of most of the people we brought there. I’m proud of a lot of what we were able to set.
“Now we just want to beat them every Sunday.”
A ‘rock star’ in DC
Brown began his next chapter by moving back to the Washington area. His wife went to the University of Maryland. His brother Omrao, an engineering student who made his career in music, had run Bohemian Caverns on U Street. Brown loved the diversity and the vibe.
Ted Leonsis, the owner of Monumental Sports, hired him to be part of a new executive leadership team with the Wizards, working alongside General Manager Tommy Sheppard with the title of chief planning and operations officer starting in 2019.
In Washington, one Monumental executive said, Brown was a “rock star” and “super smart without being in your face about it.” He helped hold the franchise together during the pandemic, a role nobody expected or knew how to play.
Brown spearheaded a project that modernized how the Wizards evaluate physiological data for players they might draft or sign, allowing them to better project injury risks. Brown made small, tangible changes aimed at culture. He altered the decor in the office and made improvements to the food program and security. He didn’t make roster decisions, but Sheppard used him as a sounding board.
“When there’s difficult situations or problems, he’s definitely somebody you want in the room,” Sheppard said. “Because he can help you solve them.”
Brown’s decision to leave for the Ravens, which came three months after he received a promotion, angered Leonsis initially, according to multiple people familiar with his thinking. But Leonsis ultimately recognized Brown could not pass up the opportunity.
For the first time, Brown will take a lead role at a franchise in a stable position, where he can be a caretaker instead of a potential savior.
“This job, this role, this responsibility is a lot different than the prior roles I had – not only in terms of types of things but also the state of the franchise,” he said. “The franchise is really healthy.
“I’m not a great-man believer, [that] there’s just one guy that sits in some room and orchestrates everything. The strength of the Ravens has always been – and will continue to be while I’m here – people as a collective but also the way we work together. You can assemble a lot of great talent. If it’s not working together the right way, you’re not going to optimize and you’re not going to excel at the level you should. ”