Bloomberg Tax
May 26, 2023, 1:00 PM

Spotlight on Boston Tax Controversy Attorney Kathleen Gregor

Rebecca Baker
Rebecca Baker

Our Spotlight series highlights the careers and lives of tax professionals around the world. This week’s Spotlight is on Kathleen “Kat” Gregor, a tax controversy attorney and litigator at Skadden, Arps, Slate, Meagher & Flom in Boston.

She advises clients disputing their taxes in administrative proceedings, federal and state courts, and international arbitration. She also counsels fintech and other blockchain companies, asset managers, and financial institutions. Before joining Skadden, she co-founded Ropes & Gray’s tax controversy group.

Gregor lives in Cambridge, Mass., with her family and their pandemic puppy, Chewbacca, who is still trying to figure out how to keep one human home at all times. She loves all things science fiction and is thrilled to share the new era of the Marvel Cinematic Universe with her 10-year-old son.

What’s your official title and what does it mean? I’m a partner in Skadden’s tax practice. I focus on tax controversy matters (meaning IRS audits and litigation), with a particular focus on international issues and those facing the asset management industry and their portfolio companies. On a day-to-day basis, my job could mean hundreds of different things, and that’s why I love it.

Free time: book, audiobook, or podcast? For snippets of free time, I’m a podcast girl—best way to feel a sense of achievement early in the day is to feel like I learned something new on my commute. But for true free time (like a real vacation), I go deep and will flip between books and audiobooks depending on whether I feel like moving or sitting.

Tax is a huge subject. What’s your area of special interest? I love international tax disputes, particularly involving an unexpected tax interpretation or problem. This could mean an issue for a multinational, but it also often involves a private investor navigating changes in law across existing investment platforms. Untangling the inner workings of the most complex areas of tax is where I have the most fun—especially because I often need to pull in my colleagues to workshop the arguments and strategy.

What’s the last movie or show that you watched and loved (DVD, Netflix, or in the theater)? Season 3 of “Star Trek: Picard.” Engage!

What college did you attend and what did you study? Georgetown University’s McDonough School of Business, where I majored in accounting with a minor in art history. Mixing the practical with what some might dub frivolous has always brought me joy.

Go-to pick-me-up: Coffee or tea? Depends on how much I need to be picked up! My dad loves coffee and my mom loves tea—I somehow inherited both.

What’s the best tax or financial advice that anyone ever gave you? Live well below your means so that you always have the freedom to take a different job, no matter how much you’re paid. It was really career advice—this gives you the ability to remove personal pressure from the calculus when attacking a difficult issue, whether for a client or internal to the firm. This has always helped me manage a high stress career and keep a level head for my clients as we navigate issues for them.

If you weren’t working in the tax profession, what would your dream job be? Archaeologist. But the Indiana Jones type—I still don’t know if that job really exists!

If you had the opportunity to make one change in the tax world—an extra credit, a disallowed education, whatever—what would it be? Switch charitable deductions to refundable credits for those making below certain thresholds—helping everyone have the power to give back and support their own causes would do wonders for local engagement in our communities.

Favorite food, snack, or candy during tax season or other busy time? Basically anything that someone else brings to me. During my days at PwC right after college, I discovered all sorts of new foods as a group of associates would rotate who was in charge of ordering in dinner each night. It’s one of the few things I miss about busy seasons as a tax accountant.

What tax news or move made the most impact on your practice or clients this past year? The new IRS funding for enforcement activities. The IRS has been underfunded for way too long, and the funding increase coincides with increased efforts to audit private equity funds and other taxpayers using complex partnership structures. While many of my clients are coming under audit for the first time, it’s often the first time the IRS exam team has audited this type of business or structure. In many ways, both sides are learning about each other, and because I’m able to help navigate that process for both sides, it’s a particularly rewarding time in my career.

If you received a big tax refund check right now, what would you do with it? Plan a big trip with my extended family and close friends to some fantastic destination that is new to us all. I can’t think of anything better than discovering a new culture or history with those I love.

You can find out more about Gregor on Linkedin and through Skadden.

You can learn more about Gregor’s law firm, Skadden, on its website.

To contact the reporter on this story: Rebecca Baker in Washington at

To contact the editor responsible for this story: Melanie Cohen at

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