Jeremy Montgomery ’07

Built for the Pace: Widener Law Alum Jeremy Montgomery Finds His Fit in Litigation

“Law school teaches you how to think and how to write, but the practical side is what really prepares you.”

Jeremy Montgomery ‘07 doesn’t just practice law, he works in it, moves through it, and, on some days, races alongside it.

As a deputy attorney general in the tort litigation section of the Pennsylvania Office of Attorney General, Montgomery represents state agencies in civil cases across 27 counties. His caseload ranges from property damage claims to fatal accidents, inmate injury cases and complex litigation involving multiple state entities.

No two days look the same, and that’s exactly what keeps him engaged.
“It really is a variety of things,” Montgomery said. “Every case is different, every agency is different, and you’re constantly learning.”

For students considering litigation or public service, his career offers a clear view of what the work demands and what it rewards.

Learning the law, then learning how to use it

Montgomery didn’t plan on becoming a lawyer. He initially set his sights on federal law enforcement until a legal writing course during his final year at Pennsylvania State University shifted his path.

Law school followed, along with an early realization.

“Law school teaches you how to think like an attorney. It teaches you how to write like an attorney,” he said. “But the practical opportunities…that’s what really prepares you.”

At Widener University Commonwealth Law School, he found that hands-on experience through moot court, trial advocacy and internships. Those opportunities helped him not only build skills, but also understand where he fit in the profession.

Mentorship played a role as well. Then-Dean of Students Elizabeth Simcox encouraged his early involvement in moot court, while Professors Ben Barros and Robyn Meadows shaped his approach to legal analysis.

It was in legal writing, though, where things clicked.

“I was always good at writing,” Montgomery said. “But learning how to tailor it, especially for appellate advocacy, that’s different.”

That experience helped him draw a clear line for his future.

“I learned I wanted to be a litigator, not a transactional attorney,” he said.

What litigation actually looks like

After earning his juris doctor in 2007 and later an LL.M. from Widener University Delaware Law School, Montgomery built his experience through clerkships and private practice before joining the Office of Attorney General, where he has spent nearly a decade.

His work now centers on legal writing, depositions, court conferences, oral arguments and ongoing coordination with state agencies.

“There’s a lot of legal writing. There are depositions. There are court conferences,” he said. “I can’t tell you that every day is the same.”

A single week might include a court appearance in one county, depositions, and preparing filings for multiple cases at once. While some travel has shifted since the pandemic, the pace has not.

“I like that fast-paced style litigation,” he said.

The advantage of being in Harrisburg

For Widener Law Commonwealth students, Montgomery sees a built-in advantage.

“The good thing about being in Harrisburg is we have a lot of government agencies that are always hiring interns,” he said.

That access, he noted, is critical. Internships and hands-on experiences remain the most effective way to prepare for being an attorney, which is why he continues to bring students into real legal work whenever possible.

“That’s the best way to prep yourself for life after law school,” he said.

Learning to think on your feet

Through his continued work coaching moot court teams, Montgomery sees how students develop into advocates.

In appellate advocacy, arguments rarely unfold as planned. Judges interrupt. Questions shift direction. Students have to respond in real time.

“You really have to know the law, and you really have to know the facts,” he said.

That ability to think on your feet, he noted, is what separates classroom learning from courtroom readiness. It’s also what keeps him coming back to coach each year.

“You get a new group of students every year,” he said. “It’s about passing on what you’ve learned.”

The reality students don’t always hear

One of the most important lessons he shares has nothing to do with winning.

“You’re not always going to win,” Montgomery said. “It’s not the end of the world. You learn from it.”

Early in his career, he approached the work as a perfectionist, taking losses personally. Over time, he learned to step back, evaluate, and grow from each experience.

He also came to value perspective, including from opposing counsel.

“Not every opposing counsel is the enemy,” he said.

Building a career that fits

Nearly 20 years into his career, Montgomery has found a balance that works for him, challenging legal work paired with time for his family.

In public service, he said, that balance is real.

“The work-life balance is number one,” he said. “I wouldn’t be able to do what I do with my family if I didn’t have that.”

For students, his path isn’t about following a single track. It’s about gaining real experience early, learning from setbacks, and finding the kind of work that fits your personal preference.

For Montgomery, that answer has remained consistent.

“I like being busy,” he said. “I like having that pace. It keeps you sharp. It keeps you engaged.”

Interview conducted in Spring 2026.