The first time I saw Andrew Rabinowitz, it was in April 2017 at Baltimore District Court, where he was representing a property management company owned by the family of Jared Kushner, President Donald Trump’s son-in-law. That day, the company had three cases against tenants at Dutch Village, one of the many large apartment complexes the Kushner Companies owned in the Baltimore area.

One tenant was a Morgan State University student facing struggles typical of residents in the Kushner complexes. She had given notice that she was moving at the end of March, having tired of the perpetually clogged toilet and the ceiling leak in her closet. But when she paid March rent via the automated system tenants had to use, the money somehow ended up with an adjacent Kushner complex, and the company started eviction proceedings — even though she had already signaled her intent to leave a few weeks later.

A sheriff’s deputy changed the locks on her door when she was out of town, preventing her from moving her things out. She got her keys back, but by then she no longer had access to a moving truck. The company was also after her for April’s rent, despite the fact that it had physically barred her from being able to move before April.

In court, Rabinowitz, a 33-year-old in a jacket and tie, spoke to the judge in a polished, even-keeled tone, in contrast to the student, who grew more agitated as the hearing went on. The judge sided with Rabinowitz, ordering the student to pay $471.23 for part of April’s rent.

When I approached Rabinowitz as he was leaving the courthouse, to ask about the company’s aggressive approach, he looked startled. “What’s the article regarding?” he said. “I’m not inclined to give a statement.”

The next day, he was back in court to defend the company against the student’s criminal complaint over the unfounded eviction. This time, he offered a deal: He agreed to let her stay, rent-free, until the end of May to give her time to move out, as long as she paid for April. Afterward, she asked Rabinowitz if he could make sure that the hot water would be turned back on. “I’m just the attorney,” he demurred. (The hot water stayed off.)

The next time I saw Rabinowitz in court was in February, almost eight years later. Kushner’s father-in-law was back in the White House. But Rabinowitz’s situation had changed. He was no longer demanding payment from beleaguered tenants. Instead, he was defending them.

I had learned of his dramatic career shift when I ran into him once in downtown Baltimore. But I needed to see it to believe it. So I tracked him down one midday at the Landlord and Tenant Branch of the District of Columbia Courts, where he now spends his days. As I spotted him, he was in a hallway speaking to a fretful older man who was seeking assistance. “Give me four minutes. Let me just go check and see if I can serve you,” Rabinowitz said, before ducking into the office of his new employer, Rising for Justice, a nonprofit that provides free legal representation to low-income tenants facing eviction.

A moment later, after attending to the man, Rabinowitz came over to say hello. He still wore a tie, but now had long hair to go along with it. He was looking far less anxious than he had when I approached him back at the Baltimore courthouse. In fact, he was positively glowing.

So much has changed in this country and the world since 2017 — much of it, arguably, not for the better. I wanted to know: What had happened with Rabinowitz?

American culture is rife with glamorous depictions of high-stakes, high-paying Big Law firms, from “L.A. Law” to “Michael Clayton” to “Suits.” But there is a humbler realm more typically glimpsed via highway billboards and subway ads. This is the level at which millions of people encounter the justice system, for better or worse.

And this is the corner through which Rabinowitz entered the profession. He grew up in Ellicott City, Maryland, outside Baltimore. His mother was dean of admissions at the University of Maryland School of Nursing; his father was chief of social work at the Armed Forces Retirement Home in Washington. He attended Frostburg State University, in western Maryland. Interested in the law, he spent a couple years as a paralegal before heading to law school at Barry University in Orlando, Florida.

His aspiration was to become a criminal defense attorney, but the job he found after getting his degree was with Barry Glazer, a colorful Baltimore personal injury lawyer known for attention-getting ads. One script went like this: “I am sick and tired of these insurance companies telling you what good neighbors they are and how you’re in such good hands. If your car is totaled and you owe more than it’s worth, they give you the lesser amount and you continue to pay a finance company the difference. Don’t pee on my leg and tell me it’s raining.” Under pressure from the Bar Association, Glazer changed “pee” to “urinate.”

It was an eye-opening experience, the first time Rabinowitz had come into regular contact with people on the lower rungs of the social ladder — people with big problems but unable to afford big firms. He left after a couple years for a small defense practice because he wanted to pursue his original aspiration. This proved disappointing. Criminal law, he found, turned out to be less a stirring quest for justice and more an exercise in squeezing fees out of poor clients in desperate circumstances.

Rabinowitz started looking around again, in 2015, and joined Jeffrey Tapper, whose small firm in the Baltimore suburb of Owings Mills specialized in representing landlords large and small as they pursued tenants.

At first, Rabinowitz liked the work. Despite his natural introversion, he had come to enjoy being in court, in front of a judge. And in this new job, he was in court a lot — as many as 10 hearings per day.

He prided himself on being able to negotiate settlements, getting landlords to accept less than what they believed they were owed and working out payment plans with tenants. This was what he recalled of the case where I had first met him — that he had been able to work out a deal with the college student to give her an extra month to move out of the Kushner unit.

He even gave some tenants his phone number, urging them to call if they ended up falling behind again, so they could work something out before it landed them back in court. He wasn’t really sure what to think when, one day, he heard a judge say to a tenant, “Step into the hallway with Mr. Rabinowitz. He’s the fairest debt collector in town.”

To many people, “fairest debt collector” sounds about as noble as “kindest executioner.” But the label was apt. A couple of times, he appeared opposite Joe Mack, a tenant’s rights attorney whom he had gone to camp with as a kid. Mack recalled Rabinowitz persuading a judge that Mack’s client had failed to provide enough notice before breaking a lease and thus owed the landlord a sizable sum. Making the loss easier to take, Mack said, was that Rabinowitz had been respectful in the courtroom. “I can imagine,” Mack added, “that some other things he was doing might have been rougher.”

My eventual 2017 article laid bare the harsher reality of many of the cases involving the Kushner complexes. The company pursued one woman for several years for about $3,000, eventually having her wages garnished, even though she had received written permission to break her lease. A second woman ended up in court after moving out from a unit with maggots coming out of the living-room carpet and raw sewage flowing out of the kitchen sink. Yet another was pursued for about $4,000 even though she had written permission to move out of a unit with black mold.

After the article appeared, the Maryland attorney general filed suit against the Kushner company, which in 2022 settled with the state for $3.25 million, though the company did not acknowledge wrongdoing. In March, a group of former tenants won class-action status in their own lawsuit against the company. The company, which denied wrongdoing in the class-action case, did not respond to a request for an interview for this article. Over the years, the company has sold most of the properties ProPublica originally reported on.

Back in 2017, a company executive had responded to questions by saying that it had a “fiduciary obligation” to its investment partners to collect as much revenue as possible from tenants, and that its practices in doing so were “consistent with industry standards.”

Rabinowitz offers a similar defense. The Kushner approach was not noticeably different from other big landlords, he said: “They were all the same.” He had no particular feelings for the company itself, and he had never actually met Kushner or any other executives. “They’re so disconnected from the property,” Rabinowitz told me. “It’s just money for them.” But he was protective of his boss, Tapper, who he felt had treated him fairly. (Tapper died last year.)

Rabinowitz himself had not set foot inside the Kushner complexes. The sorts of poor upkeep described in the article did not figure much in the cases, he said. “I know most people wouldn’t want to live in housing like that,” he said, “but I remember driving past those communities and I don’t remember being like, ‘Those were horrible places.’”

He insists he did not regret his years working for the Kushners and other landlords. There was a system in place, and he had played a part in that system. “I honestly felt that if every attorney could have had the same philosophy and treated people fair and put people in the position to take control of their life,” he said, “then debt collectors wouldn’t be such bad people. They’d be assistants to people paying off their debts.”

Still, the article instilled an unease that only grew with time. He was almost always facing off against people who lacked their own attorney, in a state with laws that were unusually favorable to landlords. “It was like a heavyweight sparring featherweights over and over again,” he said. “That’s just not satisfying.”

His longtime partner started to notice that he was agitated on nights before trials; sometimes he’d even mutter things like “objection!” in his sleep. “She could tell my mind was in court, constantly,” he said. To try and escape the burden, he went whitewater kayaking on weekends.

Around this time, his parents were nearing retirement. Accolades poured in from people they had served over the years, at the nursing schools and the retirement home. One man was wheeled in on his hospital bed to thank Rabinowitz’s father. “When I saw all the people who came out, I realized they had so much impact on so many people’s lives,” Rabinowitz said. He paused. “And I’m just putting money into rich people’s pockets.”

Then came the coronavirus pandemic. Maryland suspended evictions in March 2020, and, when the moratorium ended in 2021, it passed a law establishing (and funding) the right to an attorney for any tenant facing eviction.

Rabinowitz saw his chance. He applied for an entry-level opening in the Baltimore County office of Maryland Legal Aid. The organization recognized his experience and urged him to apply to be the supervisor of a staff of 20 in its newly expanded Baltimore City housing office. The job came with a “fairly significant” drop in pay, but he took it.

It wasn’t easy telling Tapper, who had recently offered to make him a partner in the firm before he retired. But Tapper understood. “I went to the enemy, on the one hand,” Rabinowitz said. “On the other hand, he was proud.”

The transition was awkward at first. Rabinowitz and his new colleagues at Legal Aid were occasionally facing off against a former colleague. And he could tell that some of his new colleagues were initially wary. After all, while many lawyers move from public-service roles to private practice, precious few head in the other direction. “People wanted to know if I was for real,” he said.

A few years later, Rabinowitz made his way to Rising for Justice, as director of the organization’s Tenant Justice Program. He now oversees four staff attorneys and a paralegal while supervising about nine law students from Georgetown University and the University of the District of Columbia.

It means a near-daily rail commute from Baltimore. But he likes working in the Washington court, which has such a nonconfrontational vibe that it makes do without bailiffs. The organization’s clients are grateful for the assistance, and he likes that it includes a social-service branch to help people find nonlegal help.

The law students assigned to him were surprised when they learned that their supervisor had once been on the other side. But they said it came in handy, too. “We get very emotional. It’s easy to get frustrated for your clients and wrapped up and involved,” said Savannah Myers, a Georgetown student, “and Drew has the unique perspective to say, ‘OK, well, this is what’s happening on your end, here’s probably what’s happening on the other end and here’s how you can proceed in the best way to help your client within the legal system.’”

One recent day, I watched in court as an older Ethiopian woman faced off against a landlord who was demanding back rent that she owed after having lost her job. The woman, who was using a walker, had an interpreter to assist her but no attorney. She tried to argue that the debt should be lowered because of a broken air conditioner and a problem with vermin in the rental.

After the judge, Sherry Trafford, ordered her to make monthly payments of $2,989 to the landlord, she also gently suggested that she seek out help from Rising for Justice in advance of the next hearing on her case.

“Where are they?” said the woman.

“It’s at the end of this hallway,” said Trafford.

The woman made her way slowly down, and it so happened that the person manning the intake desk at that moment was Andrew Rabinowitz. He welcomed her. “Do you have some court paperwork?” he asked through the interpreter, and then came back with a law student to assist her.

Later, Rabinowitz told me that it was poor housing conditions like the ones the woman was dealing with that were his ultimate goad these days. “That’s what motivates me,” he said. “I want people to have clean housing like mine.” Why had those conditions not registered so much with him back when he was on the other side? “I guess that stuff didn’t really get to me,” he said.

I was struck again by Rabinowitz’s reluctance to judge his earlier self. But there was no obscuring one effect of his new role. “I sleep well,” he said.