Some bourbons are so good that you can’t wait to buy another bottle. Others are so disappointing that you wouldn’t take another one if the store offered it at half price. But there’s a third category that’s a little harder to explain: bourbons that are genuinely good, sometimes even exceptional, but that you have absolutely no intention of buying again.

I’ve got a couple of those in mind, and neither of them disappointed me. In fact, I thoroughly enjoyed both bottles. But somewhere between the quality of the whiskey and the price on the shelf, something went wrong.

And as I sit here sipping a remarkably good bourbon that costs considerably less than either one, I think I’ve figured out why.

When Reputation Gets Expensive

Henry McKenna 10-Year Single Barrel Bottled-in-Bond is a good bourbon. Let’s establish that right away. It’s a 100-proof, 10-year-old single-barrel expression from Heaven Hill, and it earned an excellent reputation when you could find it for $35 or $40.

That reputation was well deserved. In fact, it was part of what made McKenna so attractive. Where else could you find a 10-year-old, bottled-in-bond, single-barrel bourbon at that price?

But then people started noticing. Awards followed. Demand increased. And before long, the price had climbed well beyond the point where the bourbon originally established its reputation.

I bought my bottle for around $70. And I liked it. There was nothing wrong with the whiskey, and I certainly didn’t regret drinking it. But I couldn’t help thinking about the other bottles on my shelf that offered comparable experiences for considerably less money.

Today, Total Wine has McKenna listed for $61. That’s an improvement, but it’s still more than I’m willing to pay. At $50, I’d probably buy another bottle. At $61, I’ll pass. And here’s why.

As I’m writing this, I’m sipping Old Grand-Dad 114 Single Barrel. Total Wine has it listed for $54. It’s a 114-proof single-barrel bourbon, and it’s an absolute banger. Rich, delicious and satisfying from the first sip to the finish. It’s one of those pours that reminds me why I fell in love with bourbon in the first place.

Now, McKenna has some advantages on paper. It’s bottled-in-bond, carries a 10-year age statement and has a well-established reputation. Old Grand-Dad brings 14 additional proof points and its own single-barrel distinction, but it doesn’t have the same age statement.

None of that changes what happens when the whiskey reaches my glass. I enjoy the Old Grand-Dad more. Considerably more. And it costs seven dollars less.

So why would I spend more money on a bourbon I enjoy less? Because McKenna has a better reputation? Because it won some awards? Because somebody else decided it’s worth more? I’m not drinking the reputation. I’m drinking the bourbon.

The Birthday Bourbon That Got Away

My other example has a much more personal story.

In 2009, I was shopping for something special to celebrate my mother’s birthday. Mom had passed away two years earlier, and I wanted to mark the occasion in a way that meant something to me.

Then I spotted a bottle of Old Forester Birthday Bourbon sitting on the shelf. Birthday Bourbon! On Mom’s birthday! It might as well have had a sign attached that said, “BUY ME NOW!”

I think I paid around $80 for it, which was a fortune to me at the time. But it was a special occasion, and I decided to splurge. And the bourbon was wonderful. I enjoyed it over the following year, eventually draining the bottle and deciding that I’d like another one.

So I went back to the store. The people there practically laughed at me.

Apparently, I’d been incredibly lucky to find that first bottle just sitting on the shelf. Birthday Bourbon had become one of those highly allocated releases that people put their names on waiting lists to purchase. Even then, there was no guarantee the store would receive enough bottles to satisfy the demand.

My days of casually picking up Birthday Bourbon were over. And things have only gotten worse.

Today, the suggested retail price is around $200. Total Wine offers it for $250 if you’re among its top-tier customers. I’m not. Outside that arrangement, the lowest asking price I’ve found is around $600, with some bottles priced at $750 or $1,000.

But here’s the really ridiculous part. That 2009 Birthday Bourbon I purchased for around $80? I’ve seen people asking between $1,500 and $1,900 for bottles from that release.

Let that sink in.

I bought a bottle of whiskey to celebrate my mother’s birthday, enjoyed it over the course of a year and now use the bottle as a decanter. Today, someone might pay nearly $2,000 for the same release and never even open it.

Would I buy another Birthday Bourbon for $200? I’m not sure. I remember enjoying the bottle, but I don’t remember enjoying it that much. At $500 or $600, there’s absolutely no chance.

Well, unless somebody finally publishes my novel, Tumbleweeds, and it becomes a bestseller. Seriously. Somebody, anybody, please help me publish Tumbleweeds. I’d really appreciate it.

When Bourbon Becomes Something Else

I understand supply and demand. I understand that some bourbons are produced in limited quantities, and that collectors are willing to pay extraordinary prices for bottles they consider special. I even understand why someone might want to preserve a rare bottle rather than drink it.

But somewhere along the way, the bourbon industry developed a strange relationship with value.

A bottle that once represented an excellent bargain becomes famous. Its price climbs because people want it. Then people want it even more because it’s expensive and difficult to find. Eventually, the reputation becomes almost completely disconnected from the experience of drinking what’s inside.

At that point, are we still talking about bourbon? Or are we talking about a collectible that happens to contain bourbon?

There’s nothing inherently wrong with owning expensive whiskey. I’ve spent more than I probably should have on bottles that intrigued me, and I’ll undoubtedly do it again. Sometimes the experience is worth the expense. Sometimes it isn’t. But I’ve also learned that an expensive bottle doesn’t necessarily deliver an expensive experience.

A $100 bourbon isn’t automatically twice as enjoyable as a $50 bourbon. Sometimes the less expensive bottle is actually better. And sometimes the difference between them is so small that paying twice as much makes absolutely no sense.

That’s what happened with Henry McKenna. The whiskey didn’t suddenly get worse. Its price simply climbed beyond what I thought it was worth, especially compared with the alternatives.

Birthday Bourbon is a little different. Its scarcity transformed it from something I could buy for a special occasion into something I can only admire from the other side of a locked cabinet.

Both are good bourbons. Neither is likely to find its way back onto my shelf.

Looking Beyond the Label

There’s a lesson here that goes well beyond whiskey.

When the prophet Samuel went looking for Israel’s next king, he was initially impressed by Eliab, one of Jesse’s sons. Eliab looked like someone who ought to be king. But God had something different in mind.

The Lord told Samuel:

“For the LORD sees not as man sees: man looks on the outward appearance, but the LORD looks on the heart.”
— 1 Samuel 16:7 (ESV)

Samuel was judging by what he could see. God was concerned with what Samuel couldn’t see. The eventual choice was David, the youngest of Jesse’s sons, who hadn’t even been brought forward with his brothers. He was out tending sheep while everyone else was being considered.

The world has always been impressed by appearances. Wealth, status, reputation, accomplishments and connections can make someone seem more important than everyone around them. But none of those things necessarily tells us much about the person’s character.

Some of the finest people we’ll ever meet have little money, no impressive titles and virtually no public recognition. They simply possess qualities that make them extraordinary human beings. Others may have everything the world considers valuable while lacking the things that matter most.

God reminds us that genuine worth isn’t established by outward appearances. It’s found in what’s beneath them.

Now, I’m certainly not suggesting that choosing Old Grand-Dad over Henry McKenna is some great act of spiritual discernment. It’s bourbon, after all. But there’s a principle worth remembering in both situations: Reputation is not the same thing as substance, and price is not the same thing as value.

We ought to be careful about allowing the world to tell us what something—or someone—is worth. And that brings me back to the glass sitting beside my keyboard.

It’s filled with Old Grand-Dad 114 Single Barrel, a $54 bourbon that I find absolutely delicious. I don’t need a prestigious label, an impossible waiting list or a four-figure price tag to convince me that I’m drinking something special.

The whiskey can speak for itself.

And if somebody wants to spend $1,900 on a bottle of Old Forester Birthday Bourbon, more power to them.

I’ll be over here enjoying what’s in my glass.

Enjoyed this? Subscribe and get future reflections, bourbon notes, and assorted nonsense delivered straight to your inbox.

Copyright © 2026 Doug DeBolt.