Before Bernie Sanders became a U.S. senator and a two-time presidential candidate, he was a new University of Chicago graduate with a college sweetheart and a dream of owning land in Vermont. That sweetheart was Deborah Shiling, later known as Deborah Messing. Little about her has been published, but what has been verified tells a clear story.
A Private Life Behind a Public Name
Deborah Shiling is an American woman best known as the first wife of Bernie Sanders. After her second marriage she became Deborah Messing, and Vermont reporters used that name when they interviewed her in 2015. She should not be confused with the actress Debra Messing, who is a separate person with a similar surname.
VTDigger reported that she was 70 in the summer of 2015, which places her birth in the mid-1940s. Beyond that, her family background, parents and early childhood have not been documented by reliable outlets. She has rarely spoken to the press, and when she did, she kept her comments short and declined to discuss her personal relationship with the senator.
Meeting at the University of Chicago
Shiling and Sanders met as students at the University of Chicago. Sanders graduated on June 13, 1964, with a bachelor’s degree in political science, and publications that have covered his early life describe Shiling as his college sweetheart. Few details of their courtship are on the record, such as who introduced them or how long they dated, so those details are left out here.
Baltimore Magazine reported that Shiling was involved in civil rights activism as a student. The magazine wrote that she apparently joined the Congress of Racial Equality in 1960 and took part in sit-ins at segregated restaurants in Baltimore. The word “apparently” matters, since the account rests on a single report, but it suggests a young woman who was engaged with the social issues of her day well before her marriage drew attention.
A 1964 Wedding and a Plot of Land in Vermont
The couple married in 1964, shortly after graduation. Baltimore Magazine reported that the wedding took place in Baltimore, a detail that surprised some readers given Sanders’ later association with Vermont and Brooklyn.
Soon afterward, the newlyweds headed to Vermont. VTDigger reported that in August 1964 they bought 85 acres in the town of Middlesex, just outside Montpelier, for $2,500. The small structure on the property, on Shady Rill Road, became known as the “sugar shack,” and locals reportedly called it a love shack. It had running water but no electricity, and the outlet noted it was never meant to be a permanent home.
The Middlesex purchase also corrects a common timeline error. Several national stories placed Sanders’ arrival in Vermont much later in the decade, but VTDigger concluded that he came to the state with Shiling in 1964. Mother Jones had linked the land purchase to Sanders and his then-wife, and VTDigger’s reporting confirms that link.
Travels Abroad
The couple did not stay in the Vermont cabin for long. According to The Washington Post, as summarized by Baltimore Magazine, they traveled to Israel and spent several months on a kibbutz. Larry Sanders, Bernie’s older brother, described that trip as part of their honeymoon. He has lived in England since the late 1960s, and the couple visited him there. VTDigger separately wrote that the two traveled through Europe as the Vietnam War was escalating.
The End of the Marriage
Roughly 18 months after the wedding, in 1966, the marriage ended in divorce. Baltimore Magazine described the marriage as lasting just under two years, which is consistent with that timeline.
Neither Shiling nor Sanders has publicly explained why the marriage ended, and no court records or interviews cited by major outlets state a reason. Claims online about disagreements over politics or lifestyle are not supported by reliable reporting, so they are not repeated here. What the public record does show is that the two stayed on friendly terms.
Marriage to Bob Messing
Shiling’s life moved on quickly. VTDigger reported that she married Bob Messing in 1967, and that in 1968 the two bought out Sanders’ share of the Middlesex property. They had a daughter about five years later. This marriage is the source of the name Messing, which is why you will see her referred to as Deborah Shiling Messing in some coverage. The outlets consulted do not give Bob Messing’s occupation or other biographical details, so none are included here.
Setting the Record Straight on Levi Sanders
One of the most persistent mistakes about Deborah Shiling concerns Bernie Sanders’ son, Levi. For years, many biographical sketches described Levi as the child of Sanders’ first marriage. VTDigger’s 2015 reporting showed otherwise.
According to that report, Levi was born in March 1969 to Susan Mott, who later became Susan Glaeser. She was Sanders’ girlfriend at the time and lived with him in the small town of Stannard, in Vermont’s Northeast Kingdom, until they separated in 1971. Shiling told the outlet she never lived in Stannard and was not Levi’s mother.
She also said she noticed the error in a news profile after Sanders became mayor of Burlington in 1981. She did not think it was important enough to correct publicly at the time, and she assumed it was a simple mistake. The 2015 report appears to be the first to name both women in this context.
Where She Has Lived Since
Sanders introduced Shiling to Vermont, and she has stayed there for decades. When VTDigger interviewed her in 2015, she was retired, lived in Montpelier and volunteered with 350 Vermont, a local climate organization. She told the outlet she considers Sanders a friend and supports his presidential bid. She gave a similar message to the Daily Mail, as quoted by Baltimore Magazine, saying she believes in him and is a strong supporter.
Sanders, meanwhile, went on to a very different public life. He ran for governor of Vermont in 1974 and 1976 and lost both times, was elected mayor of Burlington in 1981, and later served in the U.S. House and Senate. He also sought the Democratic presidential nomination in 2016 and 2020. He met Jane O’Meara, his second wife, on the night he won the mayoral race in 1981.
What Is Not Publicly Known
Many websites list a net worth, a career history, a religion, hobbies or a current address for Deborah Shiling. None of these claims could be confirmed through reliable, original reporting, so they are not included here. The most recent verified interviews date to 2015 and 2016. As a result, there is no confirmed information about her circumstances today, and any article claiming to know her current daily life should be treated with caution.
Conclusion
Deborah Shiling’s place in history is modest in size but easy to trace. She was a University of Chicago–era civil rights participant, Bernie Sanders’ first wife, a co-purchaser of a small Vermont property and, later, the wife of Bob Messing and a mother. Her marriage to Sanders lasted about 18 months, but it helped bring him to Vermont, the state that would shape his career.
She also stands as a reminder of how easily errors spread when someone chooses privacy. For half a century, a widely repeated story misidentified her as the mother of Levi Sanders, and it took a local news outlet to set that straight. Her own account, as far as she has shared it, is simple: a friendly parting, a long life in Montpelier and continued support for her former husband.
FAQs
Who is Deborah Shiling?
Deborah Shiling, later known as Deborah Messing, is Bernie Sanders’ first wife. They met at the University of Chicago and married in 1964. She has lived mostly out of public view in Vermont.
When did Deborah Shiling and Bernie Sanders divorce?
They divorced in 1966, about 18 months after marrying. Neither has publicly given a reason for the split.
Is Deborah Shiling the mother of Levi Sanders?
No. VTDigger reported that Levi’s mother is Susan Glaeser, formerly Susan Mott. Public reporting does not show any child from Shiling’s marriage to Sanders.
Why is she called Deborah Messing?
She married Bob Messing in 1967, a year after her divorce from Sanders. She is unrelated to the actress Debra Messing.
What was the “sugar shack” in Middlesex, Vermont?
It was a small structure on 85 acres the couple bought in August 1964 for $2,500. It had running water but no electricity and was not intended as a permanent home.
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