Significance of Wealth | Episode 12
The Auction House Diaries: Stories Behind Iconic Sports Memorabilia with Joe Orlando
Listen to insights on sports memorabilia and the art of collecting from one of the best in the auction house industry.
Significance of Wealth host Tom Ruggie sits down with Joe Orlando, Executive Vice President of Sports at Heritage Auctions, to explore the world of iconic sports memorabilia, record-breaking auctions, and the strategies behind curating meaningful, high-value collections. From the $24.1M Babe Ruth jersey to disciplined collecting tactics, this episode offers rare insights for collectors passionate about preserving history and building legacies.
Key Insights
During their conversation, Tom and Joe address a variety of important considerations for both collectors and industry professionals. The discussion between savvy veterans of the collecting world surfaces insights on provenance, discipline, regret, and much more.
Provenance can strengthen an item’s significance and its appeal at auction.
In 1927, Babe Ruth slugged 60 home runs, 62 if you count his fence-clearing efforts in the World Series. To commemorate that towering season of baseball lore, Ruth commissioned the production of a display of 62 baseballs, each labeled with the date and pitching victim who surrendered the home run. Multiple displays were produced, and Ruth gifted one such item to teammate Jimmie Reese.
Orlando enthusiastically describes the item, which appeared in Heritage’s Winter Platinum Night Auction, noting: “It comes with a handwritten letter from Reese to the consignor. To have an item that old that has a letter of provenance from the recipient is almost unheard of.”
The display was previously unknown to the hobby, but its discovery and associated provenance drove significant appeal at auction, where it ultimately sold for $88,450.
Without that type of letter or documentation, such a discovery can be met with skepticism from the collecting public. The letter’s existence adds to the item’s lore and value, as we can trace its ownership to Ruth’s teammate and ultimately to Ruth. The mythological slugger accompanied his gift to Reese with some inscribed banter: “To My Pal Jimmie, Some day I hope you break this record, From ‘Babe’ Ruth, Sept 15, 1931.”
Orlando also recounts his discovery of a Johnny Bench game-used glove at a sports collecting convention 25 years ago, further emphasizing the importance of documented provenance: “The thing that made it so interesting was that it came with a handwritten letter from Johnny Bench from 1977 on Cincinnati Reds stationery,” Orlando explains. “You don’t see a lot of that. When you go back to the ‘70s and before, you don’t get a lot of written documentation in terms of letters of provenance.”
Discipline is an essential characteristic of a savvy collector.
Because of their passion and curiosity, collectors are prone to chasing various items as they appear on the market. As collectors often relinquish items from their collections to make room for new ones, Orlando emphasizes the importance of discipline to avoid constant turnover. “Most collectors have to move something they like to get something they like more,” he notes. “If you fall into that trap, there’s almost too much back and forth.”
That kind of turnover can create significant frictional costs in fees, time, and effort. It also means that, when the true must-have items come to market, collectors may not have the requisite liquidity available. Those are the items collectors might regret not being able to act on.
Tom Ruggie shares his personal rule of thumb. As he reviews auction offerings, he might see and bookmark a dozen items that catch his eye. But if he doesn’t remember them the next morning, he won’t pursue them.
Both collectors note the importance of heeding a truly visceral reaction to an item. For disciplined collectors, the absence of that reaction might mean an item is better left to other motivated bidders. “If you have that visceral reaction to something, and you like it that much, find a way to make room for it,” Orlando says.
The biggest regrets among collectors are the ones that got away.
As Orlando discusses, collectors rarely regret pursuing those must-have, best-in-class items, even if it means paying over the odds. The regret that often lingers, however, is the lamentation of the ones that got away.
“I regret far more often not going after something I loved than the opposite. In my entire collecting life, I have literally never regretted paying tomorrow’s price for a great item today. I’ve never regretted it. But I have regretted not pulling the trigger when I had the opportunity.”
Orlando also highlights the merits of pursuing the best items you can afford (rather than a litany of lower-quality items). These best-in-class items tend to appear for sale less often, and when they do return, it’s often for a lot more money than the last time.
Take for instance the $24.1 million Babe Ruth jersey discussed in this episode. That jersey hadn’t sold since 2005 when it reached a $940,000 sales price. If you were skittish about that price tag, you certainly weren’t a competitive bidder in the summer of 2024. But imagine not submitting that one extra bid in 2005. What felt uncomfortable then could have resulted in a generational return today.
Orlando has practiced what he’s preached to notable effect. For instance, when Johnny Bench auctioned a treasure trove of his memorabilia, including his many Gold Glove Awards, Orlando knew he had to have the Gold Glove from the same season as the aforementioned game-worn piece (great story, starts here). He later learned that one of Bench’s friends bought many of the top available items and sent them to various museums at Bench’s discretion.
Had Orlando not acted in that moment, persisting even as the price rose uncomfortably higher, he may have never had another chance at that Gold Glove. Instead, it would rest captive in a museum collection. With so many top-tier items sold in the same auction, the available supply of Bench memorabilia was forever reduced.
A passionate Bench collector would have long regretted abstaining from the action.
One of the most prolific collectors of baseball bats, Orlando uses a unique brand of discipline to shape his collecting pursuits.
Orlando’s game-used bat collection is the envy of many baseball fans, but his insistence on discipline ensures that he has a clear direction when adding to that collection. How does he achieve that direction? By building his all-time line-up of baseball greats whose bats are personal must-haves. The fascinating discussion around Orlando’s lineup begins at 20:20, a can’t-miss water cooler talk for baseball diehards.
This line-up forms the core of his collection. He’s chasing just one more player from the line-up (listen to find out who!), and he wants the exact right bat example from the player’s career. What does the “exact” right bat look like? For Orlando, it’s a heavily used bat from a prolific period in the player’s career, when his bats had distinct defining attributes with superb eye appeal. That discerning approach, a hallmark of a mature collector, reinforces collecting discipline.
Artificial intelligence (AI) is likely to be a transformative force in assisting collectible authenticators and graders…but not an outright replacement.
Reflecting on his experience at PSA, Orlando expresses enthusiasm about AI’s ability to assist, rather than replace, human graders. He notes that the grading process is a mixture of art and science, and that AI has been previously used in grading without human intervention to underwhelming effect.
“There’s no question that AI can assist the graders when they’re evaluating something, and I think we’re going to see more and more of that over time. But I don’t think–at least at this stage–it’s a complete replacement,” he posits. “This idea that you’re going to wave a magic wand and now computers are going to grade cards, we’ve been through that before as an industry. It didn’t work. I don’t think it’s going to work now. But I think both can be brought together to make for an even better, more consistent grading process. That’s already in motion.”
The barriers to entry in the collectibles authentication industry are high. New entrants beware.
Orlando draws on his lengthy tenure in the collecting world, noting parallels to the collecting explosion during the dot-com era when the home run chase and the emergence of platforms like eBay pushed the collecting world to new heights. That growth attracted new entrants to the authentication market, just like the COVID-boom.
He suggests, though, that new grading entrants may not find the market all that hospitable: “You could have the coolest looking holders, you can boast the best technology, but branding is branding. Collectors love uniformity. It’s a big hurdle to overcome when you have millions upon millions of collectibles circulating in the marketplace that have the PSA brand on them.”
What newcomers may not realize is that collectors who have long used certain grading services become advocates for those services. The perception of that grading company as best in class bolsters the value of the many collectibles they’ve chosen to grade there. “All of these collectors that collect PSA, they’re shareholders in a sense because they’re supporting the product. Their entire collections in a lot of cases have the PSA brand across it.” Orlando hypothesizes further, “It would take a lot–not that it’s impossible–but it would take a lot for someone to make a significant dent into that brand. The barrier to entry is very high.”
Helpful Resources
- Heritage Auctions
- Heritage Auctions Schedule
- Collecting Sports Legends: The Ultimate Hobby Guide
- Destiny Family Office’s Collectibles Scorecard
Our Collectibles Scorecard looks at where you are and where you ideally want to be in essential mindsets surrounding acquiring, preserving, cataloging, insuring, valuating and ultimately transferring your collectibles. - Destiny Family Office
- Article: Four Things to Know About Your Collectibles and Homeowners Insurance
- Article: It’s Not Just Stuff: Insider Tips for Managing Specialty Collections
- Article: Sports Memorabilia Arrive as an Asset Class
The expressed views, thoughts, and opinions belong solely to the host and/or guests and are not investment recommendations or opinions issued by Destiny Wealth Partners or its affiliates. Investment advisory services are offered through Destiny Wealth Partners, LLC, an SEC Registered Investment Advisor. Destiny Wealth Partners also conducts business under the name Destiny Family Office. Destiny Family Office podcasts are the sole property of Destiny Family Office, and information provided is for informational and educational purposes only. Destiny Family Office and its affiliates are not responsible for any human or mechanical errors or omissions. Parties may not reproduce these podcasts in any form without the express written consent of Destiny Family Office. Learn more at https://destinyfamilyoffice.com/disclosures/