Headshot of Brett Greenberg from a Credit: Courtesy Washington Wizards
From left: Sashi Jones, Tommy Sheppard, Ted Lonesis, John Thompson III, Mike Thibault, and Daniel Medina Credit: Kelyn Soong

Brett Greenberg knows he looks young for his age.

“Yeah, I keep the baby face thing going,” he said with a chuckle on a recent afternoon inside Capital One Arena.

As reporters flocked to speak with Monumental Sports and Entertainment chief executive Ted Leonsis and his recent hires for the newly created Monumental Basketball operation, Greenberg stood in the back of the lounge and accepted the occasional congratulations. At one point, he turned to Washington Post reporter Candace Buckner and told her gleefully that he was now allowed to speak to the media on the record.

The 33-year-old Baltimore County, Maryland native has been with the Wizards organization since 2010, most recently serving as the team’s vice president of basketball analytics and salary cap management, but his new role will require some adjustment.

Earlier this week, Tommy Sheppard, the Wizards’ new general manager, announced that he promoted Greenberg to be the team’s assistant general manager for strategy and analytics. During a press conference to introduce the Monumental Basketball hires, Leonsis pointed to Greenberg as one of the organization’s success stories during a rocky decade.

“If you told me one day I would be in this position when I was a kid, I would’ve probably fainted, not believed you,” Greenberg says.

He attended Bullets/Wizards games as a kid with his father and graduated from McDonogh School in Owings Mills, Maryland before attending Duke University, where he was a manager for the men’s basketball team.

During a practice his sophomore year, he met Sheppard while he was in town scouting players. Greenberg made sure to leave with Sheppard’s contact information.

“I wanted to be involved in basketball,” he says. “At the time, Tommy was in an assistant GM type role, and it happened to be with the Wizards, the team I grew up worshiping.”

The following year, Greenberg met former Wizards general manager Ernie Grunfeld, who Leonsis fired in April after the team failed to reach the playoffs. The team didn’t have a job for him at the time, so after graduation, Greenberg joined the Miami Heat as a video intern. When the late Flip Saunders joined the Wizards, he transitioned the team from PC-based video technology to Mac-based technology and needed people who understood how to use it, Greenberg says.

Sheppard knew the ideal candidate for the job.

Greenberg spent four years in the Wizards’ video department before transitioning to the front office.

“I was really lucky that Ernie and Tommy, throughout the years, let me do more and more, even when I was in the video room,” Greenberg says. “I knew what I wanted to do, and they let me grow. Tommy brought me here 10 years ago, and I’ve been following his lead ever since.”

In his new role, Greenberg will be looking at salary caps, contracts, negotiations, and also how to incorporate analytics into the team’s process. “We’ve done that in the past also, but now we really feel we can take it to the next level,” he says.

Tommy Sheppard talks to Japanese media after the introduction of Rui Hachimura Credit: Kelyn Soong

During the hour-long press conference, Leonsis admitted to the crowd of reporters and Monumental employees that he’s disappointed local NBA fans. Since he bought the franchise in 2010, the Wizards have shown flashes of promise, but done more to alienate its fanbase through poor trades and a dysfunctional locker room culture.

“This community loves basketball, and I’ve let them down,” Leonsis said. “We haven’t won 50 games. We haven’t competed for a championship since we’ve owned the team”

Leonsis has developed an unconventional approach to help turn around the franchise. He elevated Sheppard, who served under Grunfeld for 16 years, and brought in new voices in hopes of making the Wizards an ideal destination for NBA players. He hired former NFL executive Sashi Brown as the chief planning and operations officer, ex-Georgetown University men’s basketball coach John Thompson III will lead the new athlete development and engagement department, and Daniel Medina will serve as the chief of athlete care and performance.

All will work for Monumental Basketball, which includes the Wizards, Mystics, Capital City Go-Go, and Wizards District Gaming, the organization’s esports operation, and report directly to Leonsis.

“We will have a full basketball board,” Leonsis said. “The idea here, when we do planning, if it’s for Wizards, Tommy will be running that … It’s not a matrix organization. Everyone knows their lines of responsibility are … I will be active in it. What I’ve learned, especially in the last couple months, is you get blamed if you’re not involved, you get blamed if you are involved. It comes with the territory … I think it’ll be a real collaborative structure.”

Part of that structure, Sheppard added, has been elevating those already in house. Promoting Greenberg was one of his first moves he made as general manager.

“It’s been an incredible ride,” Greenberg says. “We’re just really excited for the future.”