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Michael Osacky turned love of baseball card collecting into a career

Michael Osacky collected baseball cards as a kids, but was drawn to vintage cards at the age of 17 when his grandpa gave him a box of vintage cards.
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By Greg Bates

As a teenager, Michael Osacky would jump on his bicycle and head to the local grocery stores and drugstores. He was in search of one thing: modern packs of baseball cards.

In 1997, at the age of 17, Osacky’s collecting changed gears. His grandpa presented him with a shoebox of baseball cards mostly from the 1950s and ’60s.

 Michael Osacky began collecting vintage baseball cards when he was 17 years old, after his grandpa gave him a shoebox that was filled with baseball cards from the 1950s and ’60s. (Photos courtesy Michael Osacky)

Michael Osacky began collecting vintage baseball cards when he was 17 years old, after his grandpa gave him a shoebox that was filled with baseball cards from the 1950s and ’60s. (Photos courtesy Michael Osacky)

The shoebox was filled with mostly common players and the cards were in rough shape. But he remembers pulling a 1973 Topps Mike Schmidt rookie card.

“He wanted to introduce me to the older, vintage stuff,” Osacky said. “Once I saw those old cards, I quickly changed from modern to vintage.”

The cards weren’t valuable by monetary means, but they sure were sentimentally special.

“That got me in the hunt of trying to find more of them, but also learn about the values,” Osacky said. “If I’m looking at two cards, why is one worth a lot more than the other? I started asking about corners and centering and all that good stuff.”

Grandpa’s old cards lit a flame – one that still shines brightly today. Osacky is an avid collector of pre-1975 baseball cards.

Osacky is the president of He was in technology sales until he turned his passion for the hobby into a full-time gig as a sports cards and sports memorabilia appraiser. Osacky is also hired to speak on topics ranging from authentication, reprints/forgeries and what goes into determining the value of vintage sports cards and memorabilia. 

“Between the speaking engagements and appraisals, that’s taking up the bulk of my time the past couple of years,” Osacky said. “It’s great; I love it.”

The 37-year-old, who lives in Chicago, specializes in 1870-1970 sports cards and memorabilia. Forbes magazine actually named Osacky the “Dean of Cracker Jack Baseball Cards” last year. It’s a moniker Osacky appreciates.

“I tend to see a lot of Cracker Jacks,” Osacky said. “People from all over the country see me as an authority on Cracker Jack baseball cards.”

 As an appraiser, Michael Osacky is well versed in the ins and outs of autographs.

As an appraiser, Michael Osacky is well versed in the ins and outs of autographs.

The 1914 and ’15 Cracker Jack cards are iconic and rare. Those are big reasons Osacky loves both sets.

“A lot of times when I see those cards they’ll have Cracker Jack stains on the front or the back of them, because don’t forget they were inserted into those packages,” Osacky said.

The 1914 cards – which are Osacky’s favorite – were only available via boxes of Cracker Jack. The next year, however, the cards could be obtained two ways: in the packages of Cracker Jack as well as a mail-in offer where someone could send money to the company in exchange for cards. Osacky enjoys the ’14 cards more because of the scarcity with only the one method of distribution.

Osacky has nearly completed the 1914 set of 144 cards, minus a few of the key guys. He has stockpiled a number of doubles and triples of the common players over the years. He has yet to pick up the hard-to-find Del Pratt or Ty Cobb, Christy Mathewson and some other Hall of Famers. Osacky does have, however, an ungraded Shoeless Joe Jackson.

Osacky’s Cracker Jack collection of the ’15 version, which features 176 cards, isn’t as advanced as the previous year.

Osacky doesn’t have really stringent criteria when it comes to collecting Cracker Jack cards.

“I feel like if I was able to get the highest quality I’d be bankrupt because they’re so expensive,” he said. “Pretty much, I’m just happy to find any Cracker Jack card in any condition. They’re getting harder and harder to find, unlike the T206 tobacco cards. I think those cards are pretty easy to find and they’re pretty affordable. You can get a common card for $20-$25.”

Osacky really enjoys collecting Cracker Jack cards, which have great color, he added.

“It’s like a treasure hunt all the time,” he said. “Let’s say someone calls and says they have some Cracker Jacks for sale. I never know, A, what year they’re going to be, or, B, if they’re going to be original or reprints. There’s a lot of reprints floating around out there. I see that on a regular basis. A lot of times people will think that they have a Ty Cobb, a Shoeless Joe, but it was manufactured in 1980 and it’s worth about 5 cents.”

As a certified appraiser, Osacky is well educated in spotting reprints of cards. There are a few tells for any reprint.

“The original cards from 1914 and 1915 are not bright and glossy,” Osacky said. “Today when I see reprints they’re made on bright, glossy paper, and that’s not normal. A lot of times, too, if you turn the card over it could say or should say if it’s a reprint – bottom left or bottom right. Also, sometimes in the bio if it talks about the player in past tense, so ‘Ty Cobb died on XYZ date. He was inducted into the Hall of Fame.’ That’s obviously a dead giveaway that’s not from 1914 or 1915.”

 A sampling of the items Michael Osacky has seen during his time as an appraiser.

A sampling of the items Michael Osacky has seen during his time as an appraiser.

Although the two Cracker Jack sets are extremely high on Osacky’s list of top baseball card sets in the history of the hobby, they don’t crack his top three. The No. 1 set? In Osacky’s opinion that belongs to 1933 Goudey. The 240-card set is littered with Hall of Famers, including four Babe Ruths, two Lou Gehrigs, two Jimmie Foxxes and a Nap Lajoie.

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“I think it’s a great set,” Osacky said. “The colors today are just fantastic and I would say that’s really a top three collecting set. The ’33 Goudey, the ’52 Topps – which has the Mantle rookie, Eddie Matthews rookie – and then the T206 tobacco set, that’s the third top three collecting set.”

A couple of individual cards that pique Osacky’s interest are the 1951 Bowman Mickey Mantle – which is tough to find nicely centered, noted Osacky – and the 1954 Topps Hank Aaron.

Osacky vividly remembers about 10 to 12 years ago being at a card show and trying to wheel-and-deal with a dealer for a PSA 8 Aaron rookie. The dealer was asking $4,500 but Osacky was only looking to spend $3,000. The two negotiated for a while, but the lowest the dealer would drop to was $4,000. Osacky passed.

“I feel like I could have gotten it for $3,500, it just didn’t work out,” Osacky said. “Here we are today over 10 years later, that card is worth $20,000.”

Appraising, sharing stories

Over the years, Osacky has become one of the top appraisers – being certified through the International Society of Appraisers (ISA) – in the country for sports cards and memorabilia.

He travels around the states working with families, estates and museums.

“I work with a lot of former athletes and their families to assess the values of their collections,” said Osacky, whose main focus over the last couple of years has turned from collecting to appraising. “A lot of times when an athlete passes away and he’s accumulated all these awards and all these World Series championship rings and signatures, the family just really has no idea what this stuff is worth. Usually, the family doesn’t have interest in keeping it. They’re more interested in finding out the value and potentially selling it so they could put their grandchildren through college, pay down the mortgage, things like that.”

Through appraising, Osacky, who is on the road several times per month, gets to check out plenty of rare and impressive collections amassed by former athletes.

“Sometimes I run across things that I’ve never seen before or anyone’s seen before,” Osacky said. “That can make it difficult, but at the same time fun because I really have to dig deep and think about how would I appraise something because there are no prior exemplars. But I would say one of the joys of appraising former athletes’ collections is just working with the families. They almost always share some fantastic stories, very private stories.”

Osacky loves sitting down and hearing the back stories to collections and memorabilia. It helps bring the person and the objects to life.

When it rolls around for spring cleaning, people will head to flea markets and think they’re picking up rare finds. Osacky receives plenty of calls from people saying they purchased a Honus Wagner T206 card and asking if they are a millionaire. However, the card ends up being a reprint.

“I like to educate people,” Osacky said. “Just like in anyone’s line of work there’s unscrupulous and scam artists and that same thing holds true in this industry. It’s not just cards but in autographs, too. So, I try and help people not getting scammed.”

Since Osacky likes to educate, he’s always willing to share words of wisdom with fellow collectors. He’s especially happy to steer new collectors to the hobby in the right direction.

“Buy what you like,” Osacky said. “Don’t buy for investment purposes because at the end of the day, whether the item goes up or down you still have something that you like – you bought it because you like it. If you buy something for investment purpose and it goes down, not only did you lose money but you hate the item because you didn’t buy it because you liked it.”

As far as purchasing autographed items, the collector needs to be educated about whose signature they are buying. Looking at prior exemplars is extremely important and could mean the difference between a real and fake autograph.

“Just because an authenticator authenticates something that’s real, that’s great, that’s awesome, but you yourself need to feel confident in the signature,” Osacky said.

Through Osacky’s speaking engagements he’s traveled around the world and shared his advice. Last year, he went to Singapore and spoke to wealthy Asian men who are now looking at sports memorabilia as an asset class.

“These men are worth tens of millions of dollars and so for them, if they were to invest $1 million in vintage baseball memorabilia and let’s say it doesn’t work out, that’s no big deal to them because these guys are still worth $50 million,” Osacky said. “That’s been one of the big pushes I’ve seen, foreign investment.”

Another big push has been the vintage craze. Values of pre-1970s cards have skyrocketed since Osacky started collecting 20 years ago.

“Sometimes I tell people what I do and they’re like, ‘Isn’t that a dying industry?’” Osacky said. “I guess you could argue it’s dying because kids don’t collect anymore but the values of high graded rookie cards, Hall of Famers – Roberto Clemente, Hank Aaron, Mickey Mantle – have been through the roof. It’s world-record prices. Not only world-record prices the last couple of years, but on a percentage basis we’re talking 30, 40, 50 percent higher in just a couple years. That’s better than the stock market, better than pretty much anything out there.”

Greg Bates is a freelance contributor to Sports Collectors Digest and can be contacted at