He once worked for Gerry Connolly. Now he hopes to carry on his legacy

WASHINGTON — James R. Walkinshaw picked the rich blue shade on his office walls 16 years ago, but on behalf of his then-boss, Rep. Gerald E. Connolly.

Walkinshaw, who worked as the Virginia Democrat’s chief of staff for more than a decade, returned to Congress earlier this month as a member. He won a special election to finish Connolly’s unexpired term after the longtime lawmaker died in May.

His office is filled with reminders of his time with Connolly: the furniture, which looks the same, he says. A large planter pot gifted from New York Rep. Paul Tonko, who was in Connolly’s freshman class. A set of coasters emblazoned with the U.S. House of Representatives seal, first purchased from the gift shop during Connolly’s first term and now incomplete after someone nabbed a few during a meeting years ago.

“It was very strange, on the first day especially,” Walkinshaw said. “It was a mixture of sadness that he’s not here, but also pride that I think he would be happy about what we’re doing … trying to carry on his legacy and his work.”

Part of that legacy, according to Walkinshaw, is advocating on behalf of federal workers. Virginia’s 11th District is home to tens of thousands of them.

“I believe, over time, that we’ll be able to turn the tide and end the assault on federal workers,” he said of the Trump administration’s widespread agency cuts.

With workers facing another threat in the form of a looming government shutdown, this is not just a Virginia problem, Walkinshaw stressed.

“I represent a lot of them, but every congressional district has federal workers who could go without their paycheck,” he said.

Walkinshaw, who most recently served on the Fairfax County Board of Supervisors, sat down with CQ Roll Call last week to talk about his staffer days.

This interview has been edited and condensed.

Q: You were Connolly’s chief of staff from 2009 to 2019 . What moments stand out?

A: I vividly remember his orientation as a new member of Congress and how frigidly cold it was. We all have phases in our lives where a lot was happening, and that time period is that for me.

The Great Recession was raging, and we were working to pass the Recovery Act. Gerry was the freshman class whip for the cap-and-trade legislation, and we worked very hard to get that over the finish line in the House, at least.

And then the Affordable Care Act dominates that time. I remember tea party rallies outside our office and getting yelled at, and the anger around all of that, but also the elation of getting it passed.

I took a leave of absence from being chief of staff and went back to run his reelection campaign in the second half of 2010. It was a competitive district back then, and the Republican wave was building. We were paddling as hard as we could to survive that wave, and we narrowly did by 981 votes.

Q: What was his personality like behind the scenes?

A: He was somebody who appreciated the humor and the irony and the absurdity of the human condition. You have a lot of interactions with people in this job, some of them not positive. And he was always able to eventually laugh about it.

Before he was elected to Congress, he toured all the Civil War battlefields, and he was really into the troop movements in each battle. He loved all kinds of music, Ella Fitzgerald and jazz music and swing music, and he had a little bit of a throwback sense of culture and theater. You know, he was a thespian himself, and he would perform with the Providence Players, a community theater group.

Q: What was an example of his kind of humor?

A: He would read The Washington Post from cover to cover every morning, and if you saw him in the morning and he asked you about something and you hadn’t read it, he would be a little bit judgmental.

I walked in once and he was reading the obituaries, and I asked him why. He said, “James, you always want to read the obituaries.” I thought it was going to be some kind of profound reason, but he looked at me and said, “… to make sure you’re not in it.” He had a sense of comedic timing. I haven’t told anyone that yet, because I felt a little weird saying it after he died, but I think he would appreciate it. He could just make you laugh.

Q: What did you learn from Connolly on how to navigate the Trump administration?

A: To be vocal and aggressive in speaking up on behalf of the people you represent. And maybe some would say, “Well, that doesn’t actually tangibly change anything.” But it’s important to the federal workers and small businesses that have been harmed by Trump’s policies.

I do think there’s something on a human level, something psychologically and emotionally important, about people knowing their representative is speaking up for them aggressively.

And then it’s also finding ways to work with Republicans, like below the radar, on issues that are not politically charged. I would say FITARA was Gerry’s signature legislative achievement, and he worked for years with Darrell Issa to get that done, at the same time Darrell Issa was viciously and unfairly attacking Barack Obama.

They were able to have it out at a committee hearing at 9 a.m. but then later that afternoon still work quietly together on the nuts and bolts of legislation to improve how the federal government purchases IT products and services.

Q: You’ve been through a couple of government shutdowns as a chief of staff. Any advice for Hill staffers on how to navigate this one?

A: I hope this doesn’t happen, but if there’s a shutdown that goes through October, you could miss a paycheck, [even though] House staffers get paid once a month. So prepare your finances. We’ve already had some conversations, and in the past, the congressional credit union has given zero-interest loans to congressional staff to help them bridge that gap.

Each office has to decide whether to declare people essential or not. Typically, most congressional offices say their staff are essential, since it’s a constitutional function that we’re providing here. So then it becomes about supporting your constituents with information and resources as best you can.

Q: What was your last conversation with Connolly?

A: After his diagnosis in November of 2024, we would meet pretty much every weekend and have breakfast at the Silver Diner in Merrifield and talk about all kinds of stuff.

But the last conversation we had, it was a day or two before he passed away. I was in the midst of campaigning, and he was my strongest supporter, though he couldn’t physically be out there for me. So he was just peppering me with questions about the campaign and giving me advice. Obviously, he was invested in it and saw it as a continuation of his work, but he lived to talk politics. He loved it. It gave him energy, so I think he enjoyed that.