Ray Madoff Makes Sure Money Maneuvers to the Right Pockets

ray madoff


ay Madoff spends her weekends baking homemade sourdough bread, listening to audiobooks, or honing her developing squash skills. Offering a beginner bread recipe or two and scrolling through photos of the loaf of sourdough she baked for a friend, the former corporate lawyer and author’s days off are filled with passion projects like these, but her week days are spent pursuing her other passion—Ray Madoff works her nine to five teaching Boston College Law School students about corruption in charitable endeavors.

Like most interesting people in the world, Madoff’s professional journey has been a tumultuous one—marked by a transition from being a big-time corporate lawyer to a blossoming law professor to, finally, the brainy philanthropy expert she is today. After obtaining her undergraduate degree in philosophy from Brown University, Madoff became a tax lawyer, a career path she found predictable given her educational background.

“A friend of mine has a theory that all philosophy majors that go to law school become tax lawyers,” Madoff said.

Madoff’s analytical philosophy undergraduate background trained her to ask big questions—pondering the nature of goodness as a philosophy undergrad naturally led her to debate classic tax dilemmas, such as the nature of borrowing money as opposed to investing money. For nine years, Madoff exercised her analytical philosophy skills as a tax attorney before moving on to a job she was not nearly as prepared for: teaching at BC Law.

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Nearly 25 years ago, Madoff starting teaching at BC Law in what was supposed to be a one-year position. Before teaching, she worked at Hill and Barlow, a law firm in Boston, where she heard from a fellow lawyer and BC Law professor, Jim Repetti, that a visiting position was open. The visiting position job teaching a subject she hardly knew anything about—trusts and estates, which essentially explores the laws in place surrounding the property of the dead—morphed into becoming Madoff’s long-term career focus. At the time of this huge job transition, she and her growing family were barely on their feet.

“It was very stressful,” Madoff said. “I came down with shingles, we had a newborn baby, we had no house … so there was a lot of stress because I was just, you know, barely ahead of the students.”

According to Madoff, these early years in her career remain a bit of a blur. Still, she remembers them as complicated, but fun and busy. Her husband, who worked from home as a public interest lawyer, was able to watch their children as Madoff embarked on a new career path.  

Now, Madoff’s three children are no longer in need of a chaperone as she pursues her work. Amelia Nicholas, Madoff’s youngest child, senior editor of BC’s Stylus literary magazine and MCAS ’19, sees the joy her mother’s work brings her. Madoff’s career path was not straight and narrow, but in Nicholas’ eyes, her mother has succeeded in securing a job she loves.

“If there is one thing I can confidently say about my mom [it] is that she truly loves her job,” Nicholas said. “She is the happiest person I know, and a big part of her life is the work she does. She has shown me that it is important to do something you love as a career, to feel fulfilled, and now that is a goal of mine as I plummet towards graduation.”

While Madoff’s career has turned into one that brings her joy, before coming to BC, she had no prior experience teaching, let alone in a subject she had little knowledge of. Still, Madoff managed to secure her place at BC Law for the next four decades and counting. She later published a book, titled Immortality and the Law: The Rising Power of the American Dead, a brainchild of Madoff’s newfound knowledge from the class on trusts and estates she began teaching. In essence, Madoff’s book grapples with the protections—or lack thereof—of the dead in America. With its publishing, Madoff’s burgeoning interest in academic writing began.

As Madoff explains it, capitalist America is inescapable, even after death. The materialistic nature of capitalist America bleeds into the lives of not only the living, but the dead as well. Whereas American society honors the dead’s material wishes—those related to the donation of their assets and property—Madoff found that American law provides few protections for people concerned about protecting their bodies or reputations after death.

“When we think about wills law and estate taxes, [in] all those things we think about the interests of the dead,” Madoff said. “But in other areas of the law, we’re like, ‘Who cares? They’re dead.’ So for example, after a person has died, somebody can say the absolute worst things about them … But there’s no legal protection because the law says, ‘You’re beyond harm and benefit, you’re dead.’”

Madoff found that this unconscious continuation of materialism in America is the antithesis of how the dead are treated abroad. European culture tends to care less about material objects left behind by the dead and more about reputational interests or what the deceased want done with their bodies.

Although Madoff will be teaching law students about trusts and estates, as well as estate planning, next semester, she’s shifted her research focus to philanthropy overhaul. As an active contributor to the BC Law School Forum on Philanthropy and the Public Good, a BC think tank that she co-founded with BC Law adjunct professor William Bagley, Madoff argues that the treatment of our nation’s charitable endeavors is in need of a makeover.

“The idea behind [the think tank] is to create a forum where policy questions pertaining to philanthropy can be raised in a non-partisan way,” Bagley said.

With Bagley, who also serves as the director of Planned Giving at St. Mark’s School in Southborough, Mass., Madoff has hosted boot camps for world-class journalists eager to properly learn about the mechanics of philanthropy and conferences focused on philanthropy reform. What necessitates the reform Madoff and her colleagues talk about is what Madoff researches: ineffective philanthropy in the United States.

Madoff believes the impending death of our nation’s charitable endeavors lies in donor-advised funds and the immediate tax subsidies one receives for large charitable donations. Donor-advised funds essentially give the donor control over the distribution of funds to a charitable entity—though the donor receives immediate tax benefits out of the pockets of American taxpayers, they still control the distribution of their donation. This, in turn, may lead to unused donations—money sitting in an account that was intended to be used by a charity.

If an American citizen were to create a donor-advised fund for a nonprofit charity and donate $100 million, they would receive an immediate tax subsidy worth approximately 60 to 70 percent of the donation, according to Madoff. The donor, though, would still retain privileges that regulate the distribution of that money, which can in effect nullify the donation, since they are under no obligation to actually distribute it.

With such a monumental issue, Madoff asks herself this question: “How are we going to tweak or change our rules to make sure that money actually gets put to charitable use?”

So Madoff remains in limbo. She sees potential solutions—Madoff thinks that providing proper incentives to distribute the money in donor-advised funds or setting a time frame in which the funds must be distributed could help solve the issue of gridlocked, unused donation money, but proper legislation has yet to be embraced by the government.

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Her name has graced bylines of op-eds in The New York Times on this topic and other tax issues she sees. Her most recent piece titled “Trump and the Failure of the American Tax System,” published on Oct. 11, details the way in which America’s tax system works in favor of the super rich—America’s wealthiest citizens acquire wealth with the exemption of income tax and the easy evasion of other taxes. In 2017, Madoff wrote an opinion piece called “Congress’s Assault on Charities,” taking the stand that failure to adopt legislation barred vital charities from getting the funding they need. Her writing has not only publicized the issues within the American tax system and charity microcosm, but attracted positive attention.  

Though he’d never met Madoff or heard of her previously, Michael Fleming, the executive director of the David Bohnett Foundation—a Los Angeles-based nonprofit that works to improve social issues through activism—took note of Madoff’s writing in The New York Times. Fleming cold-emailed and connected with her, and eventually ended up donating to her think tank. As someone who works closely with the philanthropic foundations that fall victim to lenient tax and donation rules, Fleming values Madoff’s work for the entire philanthropy industry.

“If you look at all of the money that is sitting in donor-advised funds and is sitting in foundation endowments and then you look at all social needs out there, whatever you might care about, sometimes it’s hard to explain why so much money is parked in one place when the need is so great somewhere else,” Fleming said.

How can rules be adjusted to put donation money into drive to arrive at its rightful destination? She might not have a tangible solution yet, but Madoff has the brain power to upend our nation’s current system of philanthropy, and she’s working on it.

In between writing Times op-eds and working for a think tank, she somehow still finds time every week to bake homemade sourdough bread.  

Featured Image by Kaitlin Meeks / Heights Editor

Isabella Cavazzoni

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