Prince George’s County Executive Rushern L. Baker III, left, has a political ally and mentor in Montgomery County Executive Isiah Leggett, right. (Amanda Voisard/For the Washington Post)

Rushern L. Baker III felt overwhelmed. Struggling to balance schoolwork with a staff job on Capitol Hill, the second-year Howard University law student wanted to drop a property-law class he was certain he’d flunk. So, in the fall of 1985, he went to assistant dean Isiah Leggett for permission.

Leggett said no.

Scheduling wasn’t Baker’s problem, the dean believed. It was fear of failure.

“I was so pissed,” said Baker, who thought that Leggett, for some unknown reason, was trying to derail his future. But as he nursed his resentment that semester, he ended up earning a good grade in the course.

“I knew he could do well in that class,” Leggett recalled recently. “But I needed him to believe in himself to do it.”

Montgomery County Executive Isiah Leggett, right, mentored Rushern L. Baker III, left, when the Prince George’s county executive was a law student at Howard University. ( Montgomery County Office of Public Information)

Three decades later, teacher and student are friends and peers — the top elected leaders in Maryland’s two most populous jurisdictions. Leggett, 71, is in his third term as Montgomery county executive. Baker, who turns 57 in a few days, is in his second term as Prince George’s county executive and is widely talked about as a potential gubernatorial candidate in 2018.

Their close relationship has had a tangible impact on government and politics in both counties, which have a combined population of nearly 2 million. Leggett has had Baker’s back in difficult moments. He stood aside so Prince George’s could take the lead in trying to lure the planned new FBI headquarters to the Maryland suburbs. He coached Baker on how to sell his first proposed operating budget and dispatched a senior aide to help strengthen Prince George’s nonprofit sector.

For Leggett, Baker represents redemption for Prince George’s County and the region’s African American elected officials following the 2010 arrest and subsequent conviction of former Prince George’s executive Jack Johnson on corruption charges.

“It just devastated me,” Leggett said of Johnson, also a friend and a Howard Law contemporary for whom he had “great hopes and great expectations.”

Both Leggett and Baker believe that black politicians must contend with an extra layer of scrutiny, courtesy of a white power structure that too often assumes the worst. Each has painful stories to tell that prove their point.

Normally low-key, even somnolent, in public, Leggett is more prone to a smile or a laugh when he shares a stage with Baker. He delights in poking fun at his old student and took advantage of the opportunity when Baker arrived late to a Silver Spring news conference on homelessness this year.

Prince George’s County Executive Rushern L. Baker III (D) was questioned about his endorsement of a white candidate, Rep. Chris Van Hollen, over a black candidate, Rep. Donna Edwards, to replace retiring U.S. Sen. Barbara Mikulski (D-Md.). The questions prompted a speech from Montgomery County Executive Isiah Leggett (D) on the role of race in political endorsements. (Arelis Hernandez/The Washington Post)

“He was generally late in law school classes as well. Some things have not changed,” Leggett said, as Baker cracked up.

“He’ll always be Professor Leggett to me,” he said. “I’m always learning.”

Mentoring a generation

Baker is part of a group of aspiring leaders who encountered Leggett at Howard during his 30 years as a teacher and administrator there, starting in 1976. They include former D.C. mayor Adrian M. Fenty, Atlanta Mayor Kasim Reed, D.C. Council member Vincent B. Orange, former council member Kevin P. Chavous and former Maryland state delegate Aisha Braveboy.

To Leggett, the budding lawyers represented the essence of Howard’s mission: to train social engineers who would protect and advance black empowerment. For the students, Leggett’s life story — from rural poverty to 1960s student activism at Southern University to election in 1986 as the first black council member in then-overwhelmingly white Montgomery County — embodied a historic era of African American achievement.

He was elected county executive 20 years later and remains the only black politician in Montgomery to be elected countywide.

“He was the quiet storm,” Orange said, recalling a power and intensity of purpose that made Leggett a somewhat intimidating figure.

Braveboy, a 2000 Howard graduate, took torts from Leggett and still regards him as an ally, even though he endorsed then-state Sen. Brian Frosh over her in the 2014 Maryland attorney general’s race.

“Everyone knew they had to be prepared,” Braveboy said of her law school days. “He would definitely know if you weren’t.”

But Leggett’s self-appointed role as wise man for younger black officials is not universally appreciated. Former County Council member Valerie Ervin says she was “highly offended” by unsolicited advice Leggett gave her in early 2007, when she was serving her first term.

As a political newcomer, Leggett deliberately kept a low profile, opting not to include his photograph in campaign literature and, after he won, tempering his comments from the council dais.

Like Leggett, the outspoken Ervin was also a “first” — the first African American woman elected to the council and the only black council member at that time. As such, he summoned her to his office on a Friday afternoon and advised her to exercise caution and emulate his style.

“Let me give you an example,” Ervin says Leggett told her. “Let’s say I have nine marbles on the table, and eight of them are white and one is black. Which one of those do you notice and pay attention to?”

Leggett confirmed the conversation, which Ervin said left her feeling like this was an ally she’d be better off without.

“I got elected on my own, without his help,” she said.

‘A special relationship’

Baker is more receptive to Leggett’s counsel. In a political world filled with phony camaraderie, where officials habitually address even those they can’t stand as “my good friend,” those who know the two men describe their connection as real and enduring.

“The first thing that comes to mind when you see them together is long-lost friends connecting,” said Artis Hampshire-Cowan, Howard University’s senior vice president and secretary and a veteran Prince George’s activist. “It’s clear there’s a special relationship of mutual reverence and respect and love.”

Both are Democrats, raised in the South — Leggett in Louisiana, Baker in Georgia. They are Army veterans — Leggett a Vietnam-era captain, Baker a JAG lawyer. Both say they have been mistreated by police.

Leggett told last year of being accosted by an officer while placing a campaign sign in front of a community center after hours. In 1998, Baker was stopped by a Virginia state trooper who asked if the red Chrysler Sebring convertible he was driving — with plates signifying that the owner was a member of the Maryland House of Delegates — was his.

Both have seen their families roiled by Alzheimer’s disease. Leggett lost a sister to it last year. Baker’s wife, civil rights lawyer Christa Beverly, was diagnosed in 2010 and needs extensive daily assistance.

Leggett believes that African Americans take a special vulnerability with them into political life, where they can be unfairly tarnished as corrupt or simply not up to the job.

“I think he is protective of all his former students who actually get out in this arena,” Baker said. “He certainly knows how tough it can be.”

When he became county executive, Leggett stressed that his first priority was keeping the county’s finances in order, according to a senior aide, who spoke on the condition of anonymity to discuss a private meeting. Aside from such watchfulness being in the public interest, the aide said, Leggett thought that any sign of financial mismanagement could be used as evidence that black officials were less competent than their white peers.

That perspective is one reason that, for Leggett, Johnson’s arrest and conviction for corruption during his tenure as Prince George’s county executive were unusually personal blows.

“It placed African American [officials] in the spotlight in a very negative way,” Leggett said.

The way Leggett saw it, Baker’s success could erase some of Johnson’s failings.

First elected to the General Assembly in 1994, Baker was a rising star in Annapolis. Some colleagues saw him as a future speaker or state Senate president.

But Baker burned to be county executive. He lost to Johnson twice, in the 2002 and 2006 Democratic primaries. Leggett stayed out of both contests.

With Johnson term-limited in 2010, Baker was ready to try again. He went to see Leggett.

“I thought it was going to be a short meeting,” Baker said. But Upper Marlboro was already awash with stories of a spreading federal corruption investigation that centered on Johnson.

And so Leggett had cleared his calendar for a mini-seminar on what Prince George’s voters would be looking for in the wake of the burgeoning scandal.

“It was serious. More serious than I was ready for,” Baker said.

Leggett told Baker that his first challenge would be presenting himself — a veteran politician — as an agent of change.

The other part of the conversation was about ethics — and not just involving Johnson. Leggett recalls that he had several other African American politicians on his mind as well: Baltimore Mayor Sheila Dixon, who had just been convicted of stealing gift cards intended for the city’s poor; Detroit Mayor Kwame Kilpatrick, who in 2008 resigned after lying under oath during a whistleblower lawsuit; and U.S. Rep. Charles B. Rangel (D-N.Y.), facing ethics charges that would eventually earn him a censure from the House of Representatives.

“You have to be the person who is above all that,” Leggett said he told Baker.

Helping your neighbor

Baker, who won the county executive’s seat on his third try, is no Junior Ike. He is more impulsive than his deliberative former dean and more comfortable with risks, such as the proposal for a sizable property tax increase that failed spectacularly last spring.

But what Baker wants for Prince George’s, Leggett already has in Montgomery: good schools, robust urban centers and big corporate employers. That makes Leggett’s counsel, in Baker’s estimation, especially valuable.

When he was uncertain how to sell his first proposed operating budget to voters, Leggett urged him to reach out to constituents at community meetings before it was released — his own longtime practice — to prepare them for controversy or disappointing news.

“You go out and tell people in advance,” Leggett said.

Leggett has left his political comfort zone to bolster Baker, including when he appeared with him in a television ad urging support for an expansion of gambling in the state, part of Baker’s successful push to build a casino at National Harbor.

Leggett, who in general has opposed state-run gambling, said his former student “made a good case” for the casino’s economic benefits.

But one person familiar with the politics of gambling in the state, who spoke on the condition of anonymity to talk freely, said that Leggett “got on the bandwagon for slots because he was concerned that Rushern needed a success.”

When the FBI began its search for a new headquarters, just about every Maryland and Virginia suburb coveted the project for its job-creating potential. While Montgomery did not have an ideal parcel, most elected officials would have competed anyway, rather than ceding advantage to a bordering jurisdiction.

But Leggett said there was no point and decided not to contest Baker’s efforts to bring the FBI to Prince George’s.

“Yes, I probably went the extra step,” he said. “I want to make sure he is successful.”

A teachable moment

Leggett’s most public display of solicitude came last spring, when Baker announced his endorsement of Rep. Chris Van Hollen over Rep. Donna F. Edwards in the Democratic primary race for U.S. Senate.

Van Hollen, who represented Montgomery in the General Assembly and through seven terms in Congress, already had Leggett’s support.

But Baker’s decision was more complicated. He had worked with and admired Van Hollen when both were state delegates in Annapolis. Still, endorsing him meant turning his back on Edwards, a popular incumbent from his own, majority-black county, who was running to become the first African American woman to represent Maryland in the Senate.

So Baker asked Leggett to join him at the news conference.

Leggett stood next to Van Hollen, with a cluster of other local officials who were endorsing him. In front of them, at the lectern, Baker answered question after question from local reporters that essentially boiled down to this: Why back the white guy from Montgomery and not the black woman from Prince George’s?

“Do I feel comfortable?” Baker repeated back. “Yes, I do. And the reason I feel comfortable is I know the type of senator Chris Van Hollen will be.”

He reiterated that sentiment several different ways, until Leggett stepped forward, putting a hand on Baker’s arm. Baker relinquished the microphone.

“Let me just add a little bit to that question, because I’ll have the same question as well. And my history goes back a little bit more,” the older man said, sounding as if he was settling into a lecture.

“I was a student leader, an activist, in the civil rights era,” Leggett said. “I was arrested, thrown in jail. . . .”

“What we fought for throughout the ’60s, and throughout the civil rights era, was the right to make the right decision — and that does not mean all the time that we would necessarily back the black candidate,” Leggett said. “It may mean that we would back someone else, because that person gets it and he knows it. And I think that’s what we have here.”

As he spoke, the other officials on the stage began applauding. No one clapped harder than Baker.

Class was still in session.