The Memorabilia Man

June 17, 2014 | South Tampa Magazine | Categories: Culture, Editorial, People | Tags: Alligator Border postcards, David Rice, John Osterweil, Memorabilia Magic, Model Cities Program

John Osterweil, avid collector of just about everything, displays his treasures for everyone to see at his Tampa shop, Memorabilia Magic

Story by: David Rice

Sitting on a couch in his study, John Osterweil’s weathered hands gently graze over the signatures of legends, his mind delving into their tales of acquisition. From Babe Ruth to Diana Ross and even Ross Perot, the Savannah native has developed a sort of kitsch in collecting celebrity autographs on the leather bound surface of a baseball.

The further he digs into his cabinet, the greater the treasures he reveals. The pieces tucked away range as wide in interest as the names brandished on his valuable souvenirs and as rare as the Picasso sketches that hang in the lengthy corridors of his Davis Islands home. Collecting is Osterweil’s passion, his business and a part of his personality. Save his wife, Osterweil has collected and sold thousands of various collectibles, accumulating everything from slot machines to historic postcards and antique cap guns.


“Over the years I’ve just found items that sparked my interest and did the research into what it would take to acquire them,” Osterweil says. “I’ve got some great stuff but I think the only thing I could never part with is my wife.”

It was 1955 when Osterweil’s grandfather handed down a collection of autographs and coins to his 13-year old grandson, sparking an infatuation with collecting in young John that has been honed over the years into a fine art of sorts. Whether professionally framing or concealing his valuables in plastic, Osterweil has become a master of organization and preservation, collector aging faster than collection.

In 1972, he moved to his wife Leslie’s hometown of Tampa to take on a job with the city as a city planner in the Model Cities Program. He began collecting Tampa specific items, such as old Tampa china and even a pristine hand fan that was given to female guests who attended the grand opening of the Tampa Bay Hotel in 1891.

Over the years, he has amassed a plethora of collectibles that he works to keep organized. Despite what he considers a structured arrangement of his antiques, in 1998 his wife prompted him to turn his passion into work. To put it nicely, that meant opening a shop to hold and sell his collectibles getting it out of the house. That encouragement led to the creation of Memorabilia Magic, a gallery on Willow Avenue just north of Kennedy Boulevard that displays to the public Osterweil’s various sports and entertainment memorabilia.

“I’ve been able to turn what I love into a small business,” says Osterweil as he meanders amongst the myriad of treasures that cover his gallery office from floor to ceiling. Through collecting I’ve met a lot of great people and had a lot of great memories.”


Osterweil’s nose for history is evident in his collections. A childish glow overcomes the 69-year old father of two as he holds in his hands medallions that four star generals have given him for outstanding citizenship as a volunteer for the military and serving as a liaison for MacDill Air Force base. Whether it’s the 17th Century brass Dutch tobacco boxes that line his bookcase or the specially engraved sterling silver spoons that once graced the tables of the Tampa Bay Hotel, Osterweil has a connection with all of his collections.

Perhaps it’s the one that he is most proud of that impresses the most, however. Tampa legend, historian and civic leader Tony Pizzo was an old friend and neighbor to Osterweil and turned him onto the world of Alligator Border postcards, a series of 164 depictions of Floridian life around the turn of the 20th century.

The only complete set of postcards that remain intact, Osterweil’s collection is the basis for reproductions that are sold as souvenirs at landmarks such as the Henry B. Plant Museum. Images of African American life in the cotton fields would be considered controversial in the modern day, but in their time, they were considered as beautiful as the drawings of Ballast Point and Sulphur Springs that round out the collection. It took him 15 years to put all 164 together. The collection today is valued around $30,000.

“If you look at the images, it’s really beautiful art,” Osterweil says. “Having these sorts of things around me has been exciting.”


Some of his tokens of history and memory are invaluable or too sentimental to really slap a price on. For example, in both his office and study hang pictures of good friends Neil Armstrong and Gene Cernan, the first and last men to walk on the moon. From a bag on an office shelf, Osterweil pulls chunks of the Berlin wall that he was there to collect personally when it fell. The collectibles often tell more of a story about Osterweil and his journeys as they do their own history. It’s that sentimental value that makes him hope his treasures live on long after he’s not around to savor them.

“I’ve lived a great life and when I’m gone, it doesn’t really matter how my kids split up the stuff, I’m just happy to pass it on,” he says.

Buzzing through the clutter of his office, Osterweil toys with a 1937 Buckley Track Odds slot machine that he once played as a kid on the Georgia shore. He puts his dollar in and watches as the reels spin and spit back 50 cents. A smile on his face and youthful look in his eyes, Osterweil is genuinely happy.