Nearly 200 years ago, a miserly man who’d amassed a fortune planned to give it all away — and no one really knows why.

Maybe he had an otherworldly sense of sympathy. Maybe he was driven by religion. The history is muddy.

Oliver Smith, a farmer from Hatfield, lost his father when he was 18 months old. Growing up, he watched his mother manage the family’s financials — he had five older brothers — before women were even afforded the right to vote. After receiving his patrimony at 25, he spent decades tending to it, raising cattle, selling land and offering low-interest loans to the townsfolk. But he was notably prickly, castigating his fellow churchgoers over their wasteful desire to heat the building. And yet, he spent the last 14 years of his life writing and rewriting his will so he could take care of his community for centuries to come.

His story is a cascade of contradictions. He didn’t go to college, and as a self-taught, self-made man, he valued trades over university, but his niece, Sophia Smith, is best known for founding Smith College in Northampton. He left most of his family out of his will, including his niece, who received her inheritance after her siblings died.

“There is definitely this rumor that he was this really tightfisted, penny-pinching guy with a cantankerous character,” says Meguey Baker, curator of the Hatfield Historical Museum. “I didn’t care for him much [at first]. Because I was just like, ‘What’s going on with this guy? He just seems like a real unpleasant uncle.’”

However, Baker became a convert when she learned that Smith sat in church among boys and girls his age who, as indentured servants, were destined to a childhood of forced labor — likely the reason why he made “indigent” children the primary beneficiaries in his 24-page will.

Complicating matters is that since his death in 1845, executing the will has been entrusted to Smith Charities, which was founded in 1848 and comprised of a board of electors from eight communities and one president who deems him a visionary.

“Historians claim that every man is a reflection of the times in which he lives. Occasionally, however, there is born a man who intuitively comprehends the value of methods still untried, or theories yet unproved,” boasts the organization’s website.

Smith Charities’ website, like its primary brochure, is an ode to antiquity, written in dated language over various shades of brown. The newest text is lifted from “Oliver Smith, Esquire,” a booklet written in honor of Smith Charities’ 100th anniversary — in 1948.

Smith’s wishes — that indigent boys, “female children,” “young women” and widows of “good moral character” in eight local towns were afforded support — were meant to be carried out in perpetuity. Starting with $200,000, he wanted the principal to be invested and allowed to accumulate interest until it doubled. Then, with $30,000, Smith Charities could build an agricultural high school, which was actualized as Smith Vocational and Agricultural High School in 1908.

Additionally, $10,000 was set aside for the American Colonization Society. According to Smith’s will, this designation attempted to “free” people of color by transporting them to Liberia, or “to such other place as the said Society may select as the most suitable location”; and “for furnishing the usual supplies afforded to persons of that description” after their arrival in that country. However, the society did not accept the gift in the amount of time stipulated in the will and that money instead reverted to funding for the agricultural school in 1869. The remaining $360,000 would afford gifts to indigent people who were eventually designated as tradespeople, nurses, widows and brides.

“And it shall be the duty of the said Board of Trustees and their legal successors forever to carry into full effect all provisions of this Will,” Smith wrote.

Yet, according to the current leadership of Smith Charities, it’s been a challenge to give his money away, even as the federal government withholds critical funds, like Supplemental Nutritional Assistance Program (SNAP) payments, and, locally, 16% of the population in Amherst alone lives below the poverty level

Whatever Smith’s motivations, his vision was clear. So, is Smith Charities seeing it through?

The Smith Charities Building, Wednesday, Sept. 24, 2025, in Northampton. Staff Photo/Daniel Jacobi II
Smith Charities at a glance

Who does Smith Charities help?

Tradespeople, nurses, widows and brides in Amherst, Deerfield, Greenfield, Hadley, Hatfield, Northampton, Whately and Williamsburg. Easthampton was added to the eight original towns in 1953.

How does it help them?

  • Tradespeople in these towns have to apply before age 19, but won’t receive a gift of $1,200 until age 22, after completing an apprenticeship. 
  • Similarly, nurses must apply before age 21, but won’t get the gift of $1,200 until after graduating from nursing school. 
  • Widows who have at least one child under 18 can be gifted $600 per year until the child comes of age, as well as $200 per year for each additional child under 18.
  • First-time brides who apply within 90 days of marriage can be gifted $200.
  • All applicants must “prove” they are of “good moral character,” which requires references or recommendations.

Who makes all this happen?

Smith Charities is comprised of eight electors, one from each aforementioned town (except Easthampton), a board president and a full-time employee who serves as treasurer and will administrator. Two electors and the president are designated trustees, who are all paid annually.

Money matters

Ask Smith Charities President David Murphy about his organization, and he effuses that since 1848, it has gifted more than $9 million. He espouses the virtues of Oliver Smith. He wishes more people knew about all this, because he’s certainly done all he can to get the word out — particularly to teenagers in trade schools.

“We give them the form and they stuff it in their backpack and that’s the end of it,” he said.

During his most recent visit to Smith Vocational and Agricultural High School, he and Carla Kone, the treasurer and will administrator, brought $5 gift cards to Herrell’s Ice Cream to entice kids to fill out applications. They were met with blank stares. 

During a one hourlong meeting in September with Murphy, Kone, Trustee Richard Kisloski of Williamsburg and elector Maureen Devine of Hadley, the Gazette asked the group how they found out about Smith Charities. Kisloski got a marriage gift 57 years ago. Devine’s father was once the president.  

Kone’s mother, now 88, received gifts for graduating nursing school in 1954 and becoming a bride in 1963.

“A lot of the time, [word gets out as] a part of history, through families,” Kone said. She also noted that as part of their duties, each elector must promote Smith Charities within their town.

Kone said Smith Charities helped 18 people last year, including one tradesperson, two nurses, two brides and 13 widows.

“And we’d like more in every category,” Murphy said. “We have an account called ‘reserved for beneficiaries,’ and there’s money that carries forward, so if any given year all the kids at the voc school decide to sign up, we have the money for them.”

A room sits empty on the second floor of the Smith Charities Building, Wednesday, Sept. 24, 2025, in Northampton. Staff Photo/Daniel Jacobi II

A promising beginning

Elizabeth Porada, whose 1955 honors thesis for Radcliffe College on Smith Charities is preserved at the Northampton Historical Society, wrote about the organization’s promising beginning: “The trustees rented an office, put their first advertisements in local papers, and prepared to give money away … The number of people helped by the will increased steadily through the years. In 1936, 266 widows and 316 brides received gifts, and 200 boys and 44 girls were enrolled in the apprentice program.”

The numbers peaked in the 1940s, writes Porada, who went on to serve as a Massachusetts associate justice. “From 1943 on, the country’s expanding economy brought jobs and opportunity even into Oliver Smith’s little corner of New England, and dimmed the luster of a $500 loan-gift at the end of a three-year apprenticeship, contingent on good behavior.”

But according to Donald Ebbeling, who wrote “Courtroom Crucible: The Smith Charities” in 1976, after “board members made themselves available for speaking engagements” in the late ’50s, enrollment picked back up. In 1974, Smith Charities helped 170 widows, 273 brides, 48 tradespeople and 21 nurses.

Piles of documents sit in a room on the second floor of the Smith Charities Building, Wednesday, Sept. 24, 2025, in Northampton. Staff Photo/Daniel Jacobi II

‘Couldn’t give away’

Yet by 1985, this newspaper reported that Smith Charities “couldn’t give away” money, specifically, a total of $460,000 between 1979 and 1984. “Even as its assets grew to a record $3 million … the money was returned to the coffers of the public charity,” wrote reporter Mark Sennott. 

That year, the same reporter alleged, “Despite its increasing surpluses, Smith Charities has not advertised that it has money available, and therefore many residents of Hampshire and Franklin counties are unaware they can receive gifts.” According to Sennott, “Smith Charities officials have ignored a provision of Smith’s will that allows them to distribute surplus cash to any eligible Hampshire County recipient, and not just to people in the communities that Smith said should be considered first.” 

In the will, there is a reference to helping other locals, stating, “Now, in case there shall at any time be a surplus of the income arising under each or any of the appropriations herein made over and beyond the amount required to meet the actual — or probable — claims upon each respectively from the eight Towns aforesaid — in all such cases the said Trustees may apply such surplus to the use of Beneficiaries selected from the remaining Towns in the County of Hampshire.” However, Kone said that has never happened.

“To our knowledge, the trustees have decided at various times to pay additional monies to a given set of beneficiaries when there is some extra money at fiscal year end, but we’ve never seen gifts going to recipients outside of our nine eligible towns,” Kone said. “These type of decisions can only be made by the three trustees at a given time, although it is certainly an option.”

Getting the word out

Over the past 50 years, the number of applicants has steadily declined. “The biggest problem that we have is that we don’t get the message out or the message just doesn’t sink in,” Kisloski said. 

Murphy insists that the kids are the hardest to reach. But Lauren Devine, a counselor at Smith Vocational and Agricultural High School, said the school does its due diligence to get the word out, including handing out applications at a yearly assembly, sharing the information in emails to parents and guardians, and posting information in their Guidance Google Classroom. The nearly 600 teenagers who attend the high school come from 60 surrounding towns, she said, and, based on where they reside, about 30 seniors per year are eligible to apply. She suggests that interest might increase if Smith Charites gave to more teens — including those going on to college. 

Still, she admits, the seniors “just couldn’t be bothered,” and “parents usually don’t respond.”

“We promote it as best we can,” Devine said. “We try to get every student to complete those applications because it is free money. We do sometimes wonder if the wording is what scares them, but we reiterate that we are all willing to help fill them out.”

As for its own outreach, other than its website, Smith Charities does not have an online presence, though Kone said the trustees “have discussed various social media avenues.” While QR codes enjoyed a surge in popularity during the pandemic, today, applications for the organization must be printed out, filled out by hand and emailed or mailed back to Kone. It’s unclear how nurses or brides learn about Smith Charities, though Kone uses her personal account on Facebook, as well as the obituaries, to find widows.

Tara DeLeo of Greenfield, who lost her husband six years ago and has two girls under 18, said the organization reached out to her after his passing and started gifting her yearly. DeLeo, who works three jobs, said, “It helps me with bills. It helps me pay my rent. Any little bit that they offer helps me and the girls tremendously.”