Greg Rolen – Orange County Department of Education

Growing up and attending Serra High School in San Mateo, California, Greg Rolen had two pieces of trivia he could deploy at any party. The first is his high school teammate, Barry Bonds, who once dropped a wide-open touchdown pass when they both were stars of the football team. The second is slightly more difficult to explain. Tom Brady, yes, that Tom Brady, broke his single-game interception record. “The joke is, Brady threw nearly three times as many passes as I did,” Rolen says with a laugh, recalling his football days with the ease of someone who has long since made peace with being upstaged. What he couldn’t have known then was that the instincts he honed on the field—reading defenses, staying calm under pressure, executing when the moment demands—would serve him just as well decades later as one of the most consequential education lawyers in California.

Greg Rolen | Orange County Department of Education | General Counsel

Today, Rolen is the general counsel for the Orange County Department of Education (OCDE), a role he has held since October 2024. The department serves some of Orange County’s most vulnerable student populations and provides support and mandated fiscal oversight to 28 school districts encompassing more than 600 schools and approximately 450,000 students. For Rolen, the mission is clear: to build and lead a legal department defined by operational excellence and unwavering integrity, guided by a steadfast commitment to thoughtful, principled counsel at every level of the organization.

A career shaped by purpose

Rolen’s path to OCDE was neither linear nor accidental. A graduate of the University of San Diego with a degree in political science and history, he earned his JD from the University of the Pacific McGeorge School of Law. He credits an unlikely source for setting his professional compass: his grandmother, who was the first woman Deputy Attorney General in Wisconsin, a trailblazer whose influence quietly but durably shaped his own drive toward public service, fairness, and making things right.

After three years as a deputy district attorney in Contra Costa County and six years as a deputy attorney general for California, Rolen spent seven years in private practice before becoming the first general counsel at Mount Diablo Unified School District, where he built the legal department from the ground up, reduced costs, and led major institutional initiatives. A later stint at Haight Brown & Bonesteel placed him as the only education law specialist in an 80-person firm, a position that deepened his trial experience and sharpened his instincts across a wide range of complex matters.

“I came up through an education law firm because they needed a litigator,” he says. “I learned all about the intricate workings of a school district.”

That courtroom experience, he explains, gave him confidence that proved transferable across every role that followed.

“Being on your feet arguing, juries, motions, in front of judges—the writing—led me to thinking I can do anything,” he notes.

Stabilizing the department

When Rolen arrived at OCDE in late 2024, the environment was anything but calm. He was hired by the Orange County Board of Education amid a period of internal turbulence and institutional distrust, a dynamic he navigated deliberately, earning credibility through consistency and candor.

“The Board stood by me and trusted me during difficult times. And I stood by them, and trusted them, when the prior Superintendent refused to pay me.” Now, things are different: County Superintendent and Trustee elections have since largely gone unopposed, a quiet but telling measure of the competency built in a relatively short time.

Among the most pressing tests has been a rare, politically charged $840,000 audit from the Joint Legislative Audit Committee. Rolen approached it as he does most challenges: methodically and without drama. Orange County is the sixth-largest county in the country, and its education office operates at a scale that commands serious legal firepower. Rolen manages a staff of four attorneys and two paralegals who collectively support districts across a region serving nearly half a million students.

“This is one of the larger jobs in my field,” he says.

The work extends well beyond county lines—his team testifies before legislative committees in Sacramento and frequently travels to Washington, D.C., to advocate for the students and communities they serve. Each district may retain its own outside counsel, but sensitive matters regularly end up on Rolen’s desk, where the stakes are rarely small.

Partnering with leadership

Central to Rolen’s work is his partnership with Dr. Stefan Bean, Orange County Superintendent of Schools. The legal department is anchored by Dr. Bean’s 5-3-1 Strategic Plan, which functions as the guiding framework for everything from governance training to legislative engagement. Rolen and his team provide legal and governance instruction to superintendents across the county, building capacity across the system rather than simply reacting to it.

“We have a fantastic leader,” Rolen says of Dr. Bean. “He is one of a kind.”

The two share an ambitious goal: to elevate OCDE into the most respected county education office in the country—and by Rolen’s account, they are close to realizing it. He describes his legal philosophy in similarly forward-leaning terms: his job is not to tell people what they cannot do, but to find a way to tell them what they can. That posture, he believes, is what separates a legal department that adds value from one that merely manages risk.

OCDE also distinguishes itself through a proactive, service-oriented approach, providing legal training, educational support, and administrative services to local districts while using community outreach and sound legal guidance to address complex social issues—including immigration concerns that have created fear in some families. The department is also positioning itself to join a consolidated case against social media companies and video game companies over demonstrated harm to children, a move that reflects both legal ambition and genuine investment in student welfare.

The work & the people

Rolen is candid about the human dimensions of leading a legal team. He has spent thirty years in the field and speaks with the perspective that comes from having seen nearly everything. Developing attorneys into subject-area experts, rather than interchangeable generalists, is a priority, even when it means losing talented lawyers to other opportunities.

“I have to work from a growth mentality,” he says. “Mental gymnastics as a leader—you hate to see them leave, but you’re happy to see them succeed.”

He brings that same philosophy to training, drawing on years of guest lecturing to distill a core truth: effective legal communication, like most persuasion, ultimately comes down to basic storytelling.

Outside the office, Rolen keeps his priorities close. He has a blended family of five children, four of whom have gone into public education. With even more pride, he celebrates having not missed a Friday night date with his wife, Marisol, since 2010. He attends graduations, visits classrooms, meets with administrators, serves on the Orange County Schools Bright Futures Foundation and is attuned to what the work is ultimately for. There are earlier periods in his career when he acknowledges that students themselves can feel secondary to the political noise surrounding them. That is no longer the case.

For Rolen, the proximity to purpose—to real kids in real schools—is what transforms even the most demanding stretches of the job into something worth sustaining. After thirty years of building legal departments, arguing in courtrooms, and navigating institutional politics, he has found, in Orange County, exactly the right place to put it all to work.