Leonard Leo didn’t intend to stay long in Washington, D.C.
When he was a brand new law school graduate, Leo received an offer to clerk for Judge Randall Rader on the U.S. Court of Federal Claims in 1989. He and his then-fiancée, Sally, planned for a temporary, one-year stay in D.C.
She would transfer to Washington with her job at the Naval Air Systems Command in New Jersey, and when his clerkship ended, they would return to the Garden State.
Since it was supposed to be temporary, they rented an apartment, rented furniture, “rented everything,” Leo recalls, and left for the nation's capital.
Now nearly three decades later, Leo and his wife long ago traded in their rented furniture for couches and tables they own. And Leo, executive vice president of the Federalist Society, has become a staple of Washington with an expansive network in the legal world.
He’s been called the “judicial puppet master,” “Trump’s Supreme Court whisperer,” and the “conservative pipeline to the Supreme Court.” He has played roles big and small in the confirmations of four of the nine U.S. Supreme Court justices, including the most recent, Justice Neil Gorsuch.
Leo’s critics believe he is committed to building a court that will overturn Roe v. Wade. But Leo says his goal during the judicial selection process is not about pulling the strings to secure a particular outcome, but rather ensuring potential justices display courage and independence, and show a commitment to originalism and textualism.
“What is important is that we have a judiciary occupied by individuals who understand … they have a duty and a moral obligation to enforce the structural Constitution,” he told the Washington Examiner. “They have a duty to make sure that limits on government power are respected and enforced, and when they carry out that duty or obligation, they are in a myriad of ways preserving the worth and dignity of every human person. Because if you have a system where government can do anything, if you have a system where rights that aren’t in the Constitution can be created and things that are in it can be ignored, no one is safe.”
A ‘patriotic impulse’
Born in Northport, N.Y., in 1965, Leo spent the earliest years of his childhood living on the north shore of Long Island with his mother and father, who owned a bakery and was a pastry chef.
His father died when Leo was young, and he and his mother moved in with his grandparents.
Leo’s grandfather immigrated to the U.S. from Italy at the age of 14, and worked at Brooks Brothers as a tailor. He climbed the ladder to become a clothing designer and an executive at the company, and Leo believes his grandfather was Brooks Brothers’ last non-college-educated executive.
Today, a portrait of his grandfather sits on the bookshelf in his office at the Federalist Society’s Washington headquarters.
“There’s no doubt that my experiences early on with my grandfather helped me to understand why America was exceptional and why the freedom that our Constitution provides is what ultimately leads people to goodness and to their purpose in life,” Leo said. “My grandfather was a very hard worker. He became very successful. He was a very faithful man. He was a good family man, and he was able to thrive in all of those ways because of the freedoms that we have in our country.”
His mother later remarried to an electrical engineer she met while working in the secretarial pool at a firm on Long Island. The family then relocated to New Jersey, where Leo’s half-brother was born.
Leo initially wanted to attend college at Georgetown University, but chose Cornell University in Ithaca, N.Y. While an undergraduate student, Leo studied government, which was “less the sort of amorphous, psychological science aspects of politics, and more how’s our constitutional system structured, what are the institutions of government,” he said.
His coursework in government, and specifically his studies under professor Jeremy Rabkin, helped shape Leo’s views on the Constitution and “how that affects our freedom,” he said.
After taking Rabkin’s classes at Cornell, Leo applied to be a research assistant with the professor, and was ultimately awarded one of two research assistant positions. Ann Coulter, the conservative author and pundit, was the other.
Rabkin would go on to supervise Leo’s senior honors thesis on originalism as applied to the Free Exercise Clause of the Constitution.
Before entering law school at Cornell, Leo participated in a semester-long program in Washington that included coursework as well as an internship. During his time in the program, Leo interned on the Senate Judiciary Subcommittee on the Constitution, then chaired by Sen. Orrin Hatch, R-Utah. The chief counsel of the committee at the time was Stephen Markman — now the chief justice of the Michigan Supreme Court — and the committee’s general counsel was Rader, who Leo would eventually clerk for at the U.S. Court of Federal Claims.
It was during this internship, Leo recalls, that he was first introduced to the Federalist Society, and solidified his views on the judiciary.
Markman, Leo said, served as the president of the Washington, D.C., chapter of the Federalist Society Lawyers Division, and he would often take Leo to the chapter’s lunches at the Golden Palace restaurant in Chinatown.
The first lunch Leo attended featured then-Commerce Secretary Malcolm Baldrige. But the guest at the second lunch was then-Attorney General Ed Meese, who delivered a now-historic speech on originalism.
“That speech had an enormous impact on my thinking and really helped to crystallize my views,” Leo said.
When he returned to Cornell University at the completion of his internship, Leo said he was “determined” to be part of the Federalist Society when he started law school, either as a member if Cornell Law School had a chapter, or as a founder if it did not.
Leo founded the chapter.
The group hosted speeches by legal minds such as Raoul Berger and William Bradford Reynolds, who led the Justice Department’s Civil Rights Division during the Reagan administration and helped to manage Judge Robert Bork’s confirmation hearings.
During a Federalist Society regional conference held at Cornell, Leo met Alex Azar, now Trump’s secretary of Health and Human Services, and Brett Kavanaugh, a judge on the U.S. Court of Appeals for the District of Columbia Circuit who Trump added in November to his list of Supreme Court contenders, as well as the Federalist Society’s top officials.
After Leo graduated from Cornell Law School in 1989, he accepted the clerkship with Rader on the U.S. Court of Federal Claims.
He and Sally moved to Washington, D.C., and only expected to stay for the length of the clerkship. But when Rader was tapped for the U.S. Court of Appeals for the Federal Circuit, he thought they may be remaining in Washington longer than anticipated.
Around that time, though, he was told Judge A. Raymond Randolph, who had recently been confirmed to the U.S. Circuit Court of Appeals for the District of Columbia Circuit, was looking for law clerks. Leo spoke with the judge, and accepted the position.
“By then, we had pretty much resigned ourselves not to going back to New Jersey,” Leo said.
During the second half of his clerkship with Randolph, Leo began looking for jobs at law firms in Washington.
But the Federalist Society’s Lawyers Division at that time hadn’t been doing as well as anticipated, so the organization approached Leo and asked him to run the operation. The idea was for him to lead the division for a few years to try to turn it around, and if it wasn’t successful, the Federalist Society would shutter it.
Leo wanted in.
“There are lots of countries around the world that have very long enumerations of rights, social and economic rights, political rights, civil rights. The Soviet Union had a Bill of Rights that was multiples longer than ours. Most of these countries around the world sign on to lots of [United Nations] charters that contain fundamental rights and other freedoms,” Leo said. “But at the end of the day, those are parchment barriers without serious limitations on government powers that can be enforced. And that’s what I came to realize, that the structural Constitution was the genius of the American founding and was ultimately going to protect our freedom and our dignity as people.
“That’s why I wanted to get involved,” he said of his decision to work at the Federalist Society. “I felt that was an important enterprise, and that this was the institution that was really promoting that idea in a way that no other institution had or was going to.”
Leo accepted the job offer 26 years ago, and today, serves as the organization’s executive vice president.
“This is someone who has fallen in love with the Constitution, with the American principles, and has spent his life trying to advance those,” Carrie Severino, chief counsel of the Judicial Crisis Network, told the Washington Examiner. “He had so many opportunities. He could have gone down a route of a high-paying firm. But he was crazy about the Federalist Society, and he ended up trying to follow his heart and his patriotic impulse there, and how amazingly successful that has become.”
A vast network
Gorsuch’s 68-page questionnaire from the Senate Judiciary Committee ends with one multi-part question: “Describe your experiences in the entire judicial selection process, from beginning to end (include the circumstances which led to your nomination and any interviews in which you participated).”
“On about December 2, 2016," Gorsuch answered, "I was contacted by Leonard Leo who was working with the President-elect transition team, regarding the Supreme Court vacancy.”
Leo first came to assist the Trump campaign with its judicial selection before the 2016 election, when he received a phone call from the campaign’s then-general counsel Don McGahn.
McGahn asked Leo if he would be willing to have lunch with then-candidate Trump, who also had an idea to run by Leo.
Trump, Leo recalled, wanted to draft a list of potential Supreme Court nominees to fill Justice Antonin Scalia’s seat, and release the slate to the public.
“What he said in clear and certain terms from the very beginning was I want people who are ‘not weak,’ and I want people who are going to ‘interpret the Constitution the way the framers meant it to be,’” Leo said.
Trump’s own desires for a Supreme Court justice lined up with what Leo believes are the vital qualities one can look for in a potential nominee, which he gleaned from assisting the Bush administration with filling Supreme Court vacancies.
“The two most important things any prospective nominee to the bench can have are one, evidence of courage, and two, a demonstrable judicial record of embracing originalism, textualism, and the structural Constitution,” said Leo, who took a leave of absence from the Federalist Society to assist the Trump White House with the judicial selection process.
The Trump campaign released an initial list of 11 potential justices in May 2016, and added 10 the following September.
Democrats and judicial activist organizations, in particular, have taken issue with Leo, as well as the Federalist Society, for the role they’ve played in Trump’s judicial selection process.
In separate questionnaires to several of Trump’s nominees to the federal bench, Sen. Dianne Feinstein, D-Calif., the Senate Judiciary Committee’s top Democrat, asked whether they had contact with anyone from the Heritage Foundation or the Federalist Society, including Leo specifically, about their inclusion on Trump’s Supreme Court list.
“Why would they need to hear from me?” Leo jokes. “I’ve known them all for 20 years."
“Why it is shocking that administrations would rely on the advice and counsel of people who know top minds in the legal world when they are engaging in the process of judicial selection is dumbfounding to me,” he continued. “Why that is news is incomprehensible. There isn’t a single presidential administration that hasn’t, as part of its judicial selection process, relied on people who have knowledge of the best and brightest in the legal profession.”
While many in Washington have taken notice of Leo’s vast network of legal minds, those close to him believe he would balk at being crowned a judicial kingmaker.
“The idea of him as a kingmaker is totally wrong in my opinion, because it’s not about him, although it is him trying to use his ability to help the president find good judges and judges that will be faithful to the Constitution,” Meese told the Washington Examiner. “It’s a matter of his own integrity and commitment, rather than his personality trying to be a kingmaker.”
Ronald Cass, the dean emeritus of Boston University School of Law, recited an adage Jean Monnet, a founding father of the European Union, adopted from former Sen. Dwight Morrow, R-N.J., to describe what he said is Leo’s modesty: “There are two kinds of people — those who want to be someone, and those who want to do something.
“If you’re willing to give credit, you can take great strides,” Cass, who included Leo among his groomsmen when he married in 2004, told the Washington Examiner. “Leonard is someone who understands that and is willing to give credit to others. He wants to do something and get things done. He knows that seeking credit is antithetical to getting things done.”
Leo himself has a plaque on his desk in his office at the Federalist Society that echoes this mantra.
“There is no limit to what man can do or where he can go if he doesn’t mind who gets the credit,” the plaque reads.
The light of their lives
Not long after Leonard and Sally Leo decided to put down permanent roots in Washington, they gave birth to their first of seven children, Margaret, in 1992.
Leo describes Margaret, who was born with spina bifida, as the “light of our lives,” and said she had a “profound impact” on their faith life.
“She brought us closer to God, gave us a much deeper spirituality,” he said. “[She] didn’t do it in a metaphysical way, it was just that she had this tremendous, simple love of God.
Leo said had it not been for his daughter, who died in 2007, he wouldn’t be a daily mass attendee, and wouldn’t “have the same prayer life” he has today.
“She had an updraft that was unique and unusual and extraordinary,” he said. “And, of course, to be in the same home with her or to be her friend or family member is to share in that in a very profound way. She was someone who really put life in perspective.”
Justice Clarence Thomas has sometimes said Margaret is his best friend, Leo said, and Thomas keeps two of Margaret’s drawings under the glass on his desk.
“She had this way about her that just drew people to her,” Leo said. “She would have no compunction going up to justices, the president, whoever, and having a conversation.”
Leo recalls one instance in which, just before Margaret would undergo major scoliosis surgery, he received a phone call asking if she would like to watch President George W. Bush depart from the south lawn of the White House.
While waiting in the rope line for Bush’s departure, Bush’s scheduler brought Margaret and Leo inside, which signaled to Leo she was going to be meeting the president.
The two went inside the Diplomatic Reception Room, where they found the president waiting.
“She comes in, the president says hello to her, I hear you’re going to have some surgery. How are you doing? They have this conversation,” Leo said. “She then starts engaging him. It was really incredible. That’s the way she was. She would just draw people in.”
Leo said Margaret taught the family about their faith and love of God, and “reminded us what was important in life.”
“In a town like this, where you’re always looking over your shoulder to see who the next important person is to meet with, she would always be very focused on the individual she was with, recognizing the dignity and humanity of that person,” he said. “A very important reminder.”
On his desk, Leo keeps titanium rods removed from Margaret’s body during her scoliosis surgery. The rods, he said, were bent out of shape, and eventually protruded from her neck.
“I keep those rods on my desk as a reminder of what a bad day really is,” he said. “That’s not really anything I’m ever going to have at my job.”
Leo also believes Margaret helped instill a sense of patriotism in him.
“Look, when you’ve experienced a life with the most vulnerable in our society, could be the handicapped or the poor, in my case, the handicapped. When you’ve been exposed to the worst in the world, which I have been because of my time at the [United Nations] and as the chairman of the U.S. Commission on International Religious Freedom, how can you not think that America is exceptional?” he said. “How can you not think that our Constitution is what makes us the shining city on a hill?”
For Cass, that patriotism was on display when he and Leo attended a conference together abroad. One of the attendees, an American, delivered what Cass described as “very intemperate comments” about the then-president.
“There were one or two people who stood up and said it’s not appropriate. It’s not appropriate to use that language about the president, not out of the country and not in times of war,” Cass recalled. “Leonard was one of those two people who stood up and said, ‘This isn’t right.’
“It’s that sense of values, old-fashioned values, that I think is part of what makes him the person he is.”
From Thomas to Gorsuch
Though Leo — and by extension, the Federalist Society — has been in the spotlight for assisting with Gorsuch’s selection and confirmation, Gorsuch is only the latest nominee to bear Leo's fingerprints.
In the early 1990s, he assisted with Clarence Thomas’ confirmation, whom he had developed a relationship with while clerking on the U.S. Court of Appeals for the District of Columbia Circuit.
Then, after George W. Bush took office, Leo formed one-quarter of the “Four Horsemen” with Meese, George H.W. Bush’s White House counsel Boyden Gray, and American Center for Law and Justice counsel Jay Sekulow. Together, the four assisted the 43rd president to ensure his nominations to the Supreme Court were confirmed.
“You might think four consequential egos might have different views about things, but it worked quite seamlessly and effectively,” Gray told the Washington Examiner of the group.
Leo had pushed for Samuel Alito, in particular, to be included on Bush’s short list of potential Supreme Court nominees, as he had known the judge since the late 1980s, back when Leo was intending to practice law in New Jersey.
He had visited Alito’s chambers while he was a judge on the U.S. Circuit Court of Appeals for the Third Circuit, and Leo invited Alito to lunch after he graduated from law school to discuss the Federalist Society, as Leo expected to be involved in its New Jersey Lawyers Chapter.
“I had followed his work with some interest and felt that he was an outstanding judge, an absolutely outstanding judge,” Leo said.
Alito made the original shortlist submitted to the White House, and he was nominated by Bush and confirmed to the Supreme Court in early 2006.
It’s possible that in the coming years, Trump could have the opportunity to fill another vacancy on the Supreme Court. Justice Ruth Bader Ginsburg is 84, and Anthony Kennedy is 81.
Neither, though, has indicated they’re ready to step down. But should that occur, it’s likely Leo would play a role in that justice’s confirmation.
“He understands what it means to have conservative legal principles, not just the person who knows the senator best,” Severino said of Leo. “It’s not having a D or R after your name, it’s the constitutional principles, and it’s something that Leonard understands. Having someone like Neil Gorsuch in the Supreme Court is evident of what a great choice it was for President Trump to identify Leonard and his ability to recognize the kind of person who’s going to be the next Scalia, the next Gorsuch.”