DOWNTOWN — You can learn a lot about Chicago from its post.
Leonard Piszkiewicz, a lifelong Chicagoan, knew this all too well: He spent his life painstakingly collecting hundreds of letters documenting the transformation of his hometown from an isolated settlement of a few hundred people to the interconnected metropolis it sees today.
Piszkiewicz’s extensive Chicago mail collection, spanning from 1830 to 1950, will be displayed and auctioned February 9 from 1:00 to 3:00 p.m. at the Collectors Club of Chicago, 1029 N. Dearborn St. The pieces have a value between $3,500 and $45,000.
“Even if you’re not a stamp collector, this man’s quest to document the history of the city is worth examining,” said Charles Epting, CEO and President of HR Harmer, the company that acquired the collection. “Chicago has great architecture, it has great sports history, and the post office is just another angle through which we can tell those great stories.”
Since mail has been the “primary means of communication” for a long time, it has been “at the forefront of technological advances and social change,” Epting said.
Letters can teach historians a lot about the development of a city, not only through their content, but also because the way the envelopes are stamped shows how they were transported from one place to another.
“Seeing this collection is a way to recontextualize the city, whether you’re a stamp collector or not,” Epting said. “In the same way that a museum curator arranges pieces in a certain way to construct a narrative, that’s what Len did through letters rather than pieces of art or historical artifacts. It’s a fascinating way to take a different look at Chicago history.”
The “unprecedented” collection begins with an 1833 letter, an early piece of mail originating in Chicago that was delivered on foot, Epting said.

At the time, the city was “so small and insignificant” that the postmaster “literally wrote the word Chicago on every piece of mail” for the postmark, Epting said.
“As the harvest continues, you watch as the steamboats arrive with mail on Lake Michigan and as the railroads arrive,” Epting said. “By looking at these pieces of mail, you can trace how connected Chicago has become with the rest of the country”
Airplanes began carrying mail in 1918, and mail from Piszkiewicz’s collection shows that O’Hare Airport was an early stop along the way, Epting said. In those days, it was just a field where mail planes landed and took off.
“Through the postage in the collection, you can see a lot of the connections between the past and the present, even if a lot of that history isn’t there anymore,” Epting said. “It was destroyed, either by the Chicago fire or just by the passage of time. You can see a lot of seeds being planted for things that are still around today.
The post also immortalizes technology that has vanished over time: The collection includes evidence of an intricate underground tunnel system used to deliver mail from one side of the city to the other in the early 1900s.
“They would load these tubes with letters and use air pressure to launch them at 90mph underground,” Epting said. “It’s kind of a fun dead end. It helps you remember that for every technological advance that has had a positive impact on society, there are also ones that never went anywhere.”
In addition to the big picture developments, the letters in the collection show what it was like to live in this time period since their writers used the mail to conduct business, announce weddings, and send all kinds of other news to their families.
Epting hopes Piszkiewicz’s collection will inspire more people to think of stamp collecting as another way of storytelling, even though it might not seem like “the most exciting hobby.”
“Collecting stamps doesn’t always mean trying to collect one of each. It’s about seeing each envelope in its larger context and seeing them all as pieces of a puzzle that tells the story of the development of a major city, like Chicago,” Epting said.
“He’s taken the collection as far as possible and we’re excited to find the next generation of owners, people who are willing to continue the quest Len started in their own way.”
Listen to “It’s All Good: A Block Club Chicago Podcast”: