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Vancouver man discovers great-grandfather's letters from 1901 Canada attempt in forgotten storage box

Paul Levine uncovered over 100 letters written in Yiddish and English revealing his great-grandfather's failed attempt to make a fortune in Canada before returning to Europe.

· 3 min read · HOC Vancouver Desk
Vancouver man discovers great-grandfather's letters from 1901 Canada attempt in forgotten storage box
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A forgotten box of family memorabilia in a Vancouver storage unit has become a window into the struggles of Jewish immigrants a century ago — and the tool that unlocked it was artificial intelligence.

Paul Levine, 61, stumbled upon the discovery about a month ago while retrieving something random from storage. Inside were over 100 letters written by his great-grandfather Sam Diamondstein between 1900 and 1926, along with photos and family genealogy files his late brother Richard had compiled before his unexpected death in 1999.

Sam and his wife Dora had grown up in Latvia and became part of the Jewish diaspora after increasing persecution swept through Eastern European shtetls. Later letters reflected their settlement and assimilation in the United Kingdom after their marriage. But the early ones, written in Yiddish during Sam's courtship with Dora, held a mystery: why had great-grandfather Sam warned so heavily against Levine's family move to Canada when Levine was 14? Nobody knew what Sam had been doing in Canada or why he left.

The answer was in those letters. In 1901, Sam had travelled to Montreal in steerage on an emigrant liner seeking his fortune. What he found was discrimination and exploitation. Unable to secure work as a Jew, he was forced to pretend to be an Austrian Christian — and was scammed immediately. The employer took his luggage hostage until Sam broke into an office and stole it back. "I earn almost nothing here," he wrote.

Wages for unskilled new immigrants were about 25 cents a day. "When you have no money, there is nothing you can do," he wrote to his uncle Reuven. The Panic of 1907 wiped out what little hope remained. "The crisis has thrown people out of work by the hundreds, and I am one of them." He investigated Canada's difficult prairie homesteading program but abandoned it. After years of struggle, he returned to the U.K., where Dora waited.

To bring the archive to life, Levine enlisted the help of Fernando Medrano, a Vancouver-based creative director. Together they used artificial intelligence to digitize, translate and contextualize the material, creating an online archive called A Box of Letters. They used Google Gemini for Yiddish translation, Transkribus for text recognition of cursive Yiddish, and Claude for developing larger themes and shaping narrative.

To guard against AI's tendency to hallucinate, they built in checks and balances: three independent translations of each Yiddish letter, comparison across platforms, and validation by Yiddish speakers sourced through Facebook. They also worked with a local historian to ensure accuracy of historical context.

"Be skeptical of what it produces. Things need to be run through humans. AI makes mistakes," Levine advises others considering AI for genealogical research.

Eventually, after leaving Canada, Sam and Dora settled in the U.K., had three daughters, and with seed money from Dora's dowry, Sam was able to set up a prosperous fur business in Europe. The archive now stands as testament to the lives of immigrants — their resilience, their struggles, their hopes.

"I only knew them as old people," Levine reflects. "In retrospect, you see that everyone was once young and struggling and trying to make their way in the world."

The facts

When did Paul Levine find the letters?

Paul Levine discovered the letters about a month before the article's publication on Sunday, August 9, 2026, which places the discovery around early July 2026.

How many letters did Sam Diamondstein write?

Sam Diamondstein wrote over 100 letters between 1900 and 1926.

Why did Sam Diamondstein leave Canada?

Sam Diamondstein faced discrimination and exploitation in Montreal starting in 1901. Unable to find work as a Jew, he was scammed by an employer, earned almost nothing as an unskilled immigrant, and lost hope after the Panic of 1907 threw many people out of work.

What tools did Paul Levine use to translate and digitize the letters?

Paul Levine and Fernando Medrano used Google Gemini for Yiddish translation, Transkribus for text recognition of cursive Yiddish, and Claude for developing larger themes. They verified accuracy through three independent translations of each letter, comparison across platforms, and validation by Yiddish speakers.