In the Heart of Pittsburgh

When Cliff Levine crafts an argument, he always tries to keep the big picture in mind.

In 2017, the League of Women Voters challenged Pennsylvania’s congressional district map as an unconstitutional gerrymander. Levine, representing the lieutenant governor, who supported the league’s effort, had a novel idea for enhancing its argument before the Pennsylvania Supreme Court.

“There was a question about what level of scrutiny the court should use to evaluate the congressional map—whether it should apply an elevated standard like strict scrutiny or a rational basis test,” says Levine, who chairs Dentons Cohen & Grigsby’s Government Law and Regulatory Practices and Appellate Advocacy groups and has more than 100 published appellate court opinions. “In a separate context, the court had overruled legislation involving maps while employing the more deferential rational basis standard. The court has considered ‘spot zoning’ challenges where, for instance, a commercial or industrial use designation is allowed on a small parcel within a residential district. The court has ruled that would violate the substantive due process of the residents of that district. Therefore, it was not a stretch to consider a statewide congressional map and conclude that the configuration of districts was so irrational and inconsistent with accepted constitutional standards that it could be struck down, even under the more deferential review standard. So when addressing the Pennsylvania Supreme Court, one of the positions we presented was that ‘it’s not so unusual to look at a map and recognize where something is inherently out of place, just like the court has done in cases involving substantive due process challenges in a land use context.’”

Levine explains the connection—from behind his standing desk as if he were casually presenting at a podium—not just because the 2018 victory draws a clear line between his expertise in land use and elections, but also as a glimpse into his way of thinking, working through a theory until he finds a historical or legal precedent that tells the right story.

“I think there’s a lot of times where everybody is so specialized they don’t necessarily see that there should be greater uniformity in the legal concepts,” he says. “A good lawyer is not just looking at your case. You’re coming up with how you tell the story and anticipating what the other side might say, where a judge might express some concern. What I’ve always liked about practicing law is it’s very logical, but it’s also hugely creative.”

The approach has led to landmark decisions on a wide range of issues, including election matters, major land use and energy law cases, the tax status of the state’s colleges and universities, and the constitutionality of its medical marijuana program.

“I’ve known Cliff for over 20 years, and he has argued before our Supreme Court many, many times,” says Pennsylvania Supreme Court Chief Justice Debra Todd, who also appointed Levine to the CLE Board, which he chaired. “He is among that small group of appellate advocates that you know from the get-go are going to do a great job. His briefs are strong. He’s a tremendous oral advocate, and he’s handled some of the most high-profile and difficult cases that have come across our desks. He’s comfortable in the courtroom. He’s not a lawyer who reads his presentation. He knows his cases inside and out and presents the oral argument as if he’s having a dialogue with the court, which is the best kind of oral argument. We’re not going to be swayed by passion or theatrics. We want a good cogent argument, and he is always ready for that.”

Judge Michael Wojcik of the Pennsylvania Commonwealth Court, who has known Levine for 30 years, first as a colleague at Thorp Reed & Armstrong, then an occasional adversary when Wojcik was the Allegheny County solicitor, and now presiding over his appellate cases, agrees.

“There’s an old adage—and I’ve found since I’ve been on the bench there is more than a kernel of truth to this: ‘A good lawyer knows the law, a better lawyer knows the judge,’” Wojcik says. “I have a corollary on that: ‘The best lawyers are known by the judges by both reputation and work product.’ Cliff hits all of those. He’s an incredibly bright lawyer, a tireless advocate, very creative, and I think what sets him apart from most is he’s very tenacious; he’s a good guy to have on your side, a bad guy to have against you. If I have a problem in Cliff’s wheelhouse, he’d be the first person I’d call.”

That wheelhouse includes everything from litigation as state election counsel to Joe Biden, Hillary Clinton and Barack Obama during their presidential campaigns to his complex regulatory and land use docket. “A lot of the skyline of Pittsburgh is accredited to Cliff’s work, getting through very complicated projects through the byzantine zoning workings of both the city of Pittsburgh and the Commonwealth of Pennsylvania. Things that seemed like dead-bang losers he was able to pull out of the fire,” Wojcik says. “He’s also been involved in the transitions for pretty much every governor since I’ve known him. He’s the guy that the elected officials reach out to when they want advice about how to set up their administrations, and he’s helped guide the local, county and state executives on getting themselves off on the right foot.”

Levine’s political connections tend to place him at the center of the action. He’s served as a delegate at four Democratic National Conventions. He’s traveled to Israel with then-Senate candidate Bob Casey and ate breakfast with human rights activist Natan Sharansky. He threw his support behind “Barry” Obama—who happened to have been a 6th grade classmate of his brother-in-law’s in Hawaii—before most of the rest of the Democratic establishment caught on. He shook Rudy Giuliani’s hand inside the Williamsport courtroom where he appeared to challenge ballot counting in 2020—then ran to the bathroom to wash his hands as news of the White House COVID outbreak broke.

Then there’s the time he made headlines himself for helping to save a busload of people. On the last shuttle home from Gov. Josh Shapiro’s inauguration celebration in early 2023, Levine noticed the driver was unconscious and took the wheel on the Pennsylvania Turnpike. “It was dark and there were maybe 30 people on the bus, with me in the second row,” he says. “I noticed the bus was drifting a bit, then kept drifting, so I started to get up to see if the driver was OK when he hit the middle barrier. He was completely out, so I reached over to grab the steering wheel, but his foot was still on the gas pedal and we were going 70 miles per hour. This woman came up, and she helped to get his foot off and handbrake it as I was steering. It turned out to be a nurse, and the lieutenant governor’s aunt.”

What I’ve always liked about practicing law is it’s very logical, but it’s also hugely creative.

Levine grew up in Buffalo, New York, when it still felt like a pedestrian city, with neighborhood bookstores and record shops surrounding the University at Buffalo’s campus. Even as a kid, he recognized and loved the density, then watched with disappointment as the college and the football stadium abandoned the city for the suburbs.

After college at the State University of New York at Albany, during which he worked at the speaker’s office in the New York State Assembly and cultivated his interest in politics, he went to law school at Duke University. He fell in love with constitutional law and—as a former high school drama kid—the theater of the courtroom. He almost accepted an offer at a firm in Los Angeles where he’d completed a summer job, but decided he wanted to build a life in Pittsburgh.

“I felt like LA was like 6 million electrons with no nucleus,” he says. “Pittsburgh was very compact. It seemed like it had the potential to be a Boston of the Midwest. It was concentrated, and I really wanted to live in the city. If you go back three or four decades, there were less areas to move to that were in the city.”

Like the iconic Fred Rogers, Levine chose the historic Jewish neighborhood Squirrel Hill as his home (“I live in Mr. Rogers’ neighborhood,” he says. “Literally.”) and got involved in Pittsburgh politics and government, campaigning for Tom Murphy’s unsuccessful 1989 mayoral bid and his successful 1993 one. Murphy then appointed Levine to serve on both the city’s planning commission and zoning board for 12 years—just when Pittsburgh was reclaiming its waterfront.

“We built the football stadium, the baseball stadium, did the trails, redid the zoning code so that there was much more urban flavor—not a 1950s suburban model but really a new urban model,” Levine says. “Pittsburgh became this model of transformation of these older industrial cities into more vibrant areas. So some of the things I was initially attracted to, like the compactness and uniqueness of city neighborhoods, were things that he pushed and accelerated.”

Levine also served as part-time solicitor to the Pittsburgh Water and Sewer Authority during this time, as the city was managing consent orders to improve older systems, all while building his law practice, tackling complex regulatory and infrastructure puzzles for business clients.

“He was at the forefront of getting the cellphone system built in Pennsylvania,” Wojcik says. It was no small feat, considering Allegheny County alone has 130 municipalities. “He really was able to persuade these localities, who are kind of NIMBYs, if you will, of the net positives of building out the cell system.”

“His is an interesting practice,” adds Dentons shareholder William Taxay. “He does his political stuff but is also a very creative land use lawyer and commercial litigator. I use him primarily on things touching real estate where we need creativity. He worked on a matter for me where he had to raise a novel inverse-condemnation argument and was able to unstick a substantial development. I have found him to look at difficult problems in a different way, and as part of a team we’re able to come up with solutions.”

Pamela Austin, formerly of McCaffery Interests, jokes that her eight years on the Terminal project is a memory she’s blocked out, but she does remember how Levine, as zoning counsel, helped navigate a host of complications involving historic review, public-private financing, flood plains, land swaps, parking, traffic and signage for the novel, five-block marketplace.

“He is very thorough and strategic, and he was able to identify the correct people to get into the room to solve the issues, which is half the battle,” says Austin, now with Burns Scalo Real Estate. “He had the ability to reach out and they would respect him and call him back, so we were able to deal with these things. I wouldn’t say it was expedient, because of the complexity, but we were able to solve them eventually, and his thorough knowledge of Pittsburgh and the code and personalities was very helpful.”

Wojcik, while solicitor in 2004, also witnessed Levine’s thorough knowledge of the law and personalities as it relates to election matters.

“That presidential election was the first year they used the provisional ballots, so it was quite a chaotic scene,” he says. “Cliff managed a significant amount of election day litigation that was devolving quickly into chaos in the courtroom because there were multiple parties involved, all wanting to either close polling places, open polling places, extend time, impound voting machines, get more ballots, and Cliff throughout had a very cool head.”

Levine somehow managed to keep that cool head through the 2020 cycle despite having 15 published opinions related to election challenges. “It really became this aggressive battle over the validity of each and every vote,” he says.

At the Pennsylvania Supreme Court, Levine successfully defended the state’s universal mail-in ballot law against a constitutional challenge as co-counsel with former solicitor general Seth Waxman. “We traced the history of voting, and how the ballots were developed in the late 19th century,” he says. “We made an argument there was a transformation in the method of voting, and we relied on a provision that allowed the state legislature to have some discretion in the method of voting, and that was ultimately what the court ruled.”

In another landmark state Supreme Court case involving the tax status of public universities, he went all the way back to Elizabethan law of the 1600s that defined the concept of what charities were and what should be taxed, in order to establish that his client, Washington & Jefferson College, still met the purpose of a public charity under the original law.

And in a pending state Supreme Court case over whether Wilkinsburg can be annexed into the city of Pittsburgh, he’s arguing that a dormant 1903 law defining the annexation process should be applied.

They’re all examples of Levine working a theory more creative than the textualist approach he says appellate and regulatory lawyers often adhere to. “It’s important to understand the larger context of the law before you can credibly address a textualist argument. Some people get into the weeds of each word and comma in a sentence, when I say, ‘Let’s step back,’” he says. “It’s really all about the storytelling. A lot of lawyers get obsessed with how they’re presenting information without figuring out how their client can wear the white hat if possible. Even at the appellate level, the judges might not always acknowledge this, but if they’re sympathetic, I think they’re more receptive to grant some type of favorable outcome to that party.”