Corti Brothers is a gourmet grocery store in Sacramento, California, that in the 1980s became one of the earliest buyers for Julian Van Winkle III’s bourbon, which he was buying from Stitzel-Weller and bottling at his Old Commonwealth distillery. The people at Corti Brothers were far ahead of the whiskey curve, and they ordered 19-year-old bourbon at a time when well-aged American whiskey was practically non-existent – bottles like this one constitute the first known private-barrel bourbon selection. It was Darrell Corti, who ran the business at the time, who first convinced Van Winkle to use a cognac-style bottle. Today bottles from Van Winkle that carry the Corti Brothers name rank among the rarest and most sought-after whiskeys in the world.
Van Winkle Special Reserve 20-Year Old-Cork N Bottle 90.4 Proof
Estimate: $20,000 – $30,000 

Gordon Hue, the owner of the Cork N Bottle liquor store in northern Kentucky, teamed with Julian Van Winkle III in the 1980s and 1990s to create some of the most iconic whiskeys America has ever seen – including this, among the first 20-year-old bourbons offered by Van Winkle and a complete game-changer in terms of pushing up age statements on American whiskey, at a time when bourbon appreciation was at its nadir. Today, the Cork N Bottle releases of Van Winkle Special Reserve rank among the pinnacles of the legendary label.
D.H. Cromwell 15 Year Black 1999-2000
Estimate: $15,000 – $20,000 

One of the rarest whiskeys produced by Julian Van Winkle III at his Old Commonwealth Distillery, this bottle – one of just 72 – pays tribute to a famed Milwaukee bar owner named Helen Cromell (she often added a W to her last name because she said it was easier to remember). Nicknamed Dirty Helen for her spicy vocabulary, she was a diehard fan of Old Fitzgerald bourbon and a close friend of the Julian “Pappy” Van Winkle. Cromell died in 1969, and in 2000 Van Winkle III prepared this one-time release in coordination with Gordon Jackson, owner of Old Town Liquors in Louisville. True to her personality, the letters VGS on the label stand for “Very Good Sh!@.”
LeNell’s Red Hook Rye 23 Year Old Barrel #1 67.6 abv
Estimate: $20,000 – $30,000 

In the 2000s, LeNell Santa Ana Camacho owned a specialty liquor store in the Red Hook section of Brooklyn. Ahead of her time, she reveled in American whiskey: She not only carried brands like Pappy Van Winkle in her shop, but she traveled to Kentucky to see how she could source more. On one of those trips, she met Drew Kulsveen of the Willett distillery; they got to talking, and soon the two were selecting four barrels of rye whiskey, aged between 23 and 24 years and bottled at cask strength. It was a great choice: the barrels came from a legendary run of whiskey distilled at the Bernheim Distillery, in Louisville, in the early 1980s. Other legendary whiskeys came from the same batch, like Rathskeller Rye and the Bitter Truth, but LeNell’s Red Hook Rye has emerged as the most distinctive and sought after American whiskey, perhaps of all time. To top it all off, this bottle is signed by LeNell herself.
Rathskeller Rye 136 Proof
Estimate: $18,000 – $24,000 

Built by two German immigrants in an opulent European style, the Seelbach is Louisville’s grandest hotel. In its basement sits the Rathskeller, a ceramic-encrusted pub that today is used as a ballroom. In 2007 the hotel’s owners commissioned the Willett Distillery to bottle two whiskeys, a bourbon and a rye, to commemorate its rich history. The 24-year-old rye, known as Rathskeller, came from the same run of whiskey that went into bottles like Doug’s Green Ink and LeNell’s Red Hook Rye.
Michter’s Single Barrel Rye 25 Year Old 117.3 Proof
Estimate: $15,000 – $20,000 

Beginning in the late 1990s, the spirits importer Joe Magliocco and his team at Michter’s, a brand he had resurrected a few years earlier, began buying up old stocks of bourbon and rye from distilleries around Kentucky. They bottled them first at 10 years old, then later at 25 years. The first 25-year-old rye release, including this bottle, appeared in 2011, and quickly set the standard for what great old rye should taste like. At the time Michter’s contracted with Willett to bottle for them. After 2013, Michter’s did the bottling themselves.
Old Rip Van Winkle 18 Year Old Blue Smoke 92.6 Proof
Estimate: $20,000 – $30,000 

The early 2000s were a high time for Julian Van Winkle III – he signed an agreement to distill and bottle his brands at Buffalo Trace, ensuring a future for the Van Winkle label, while at the same time he bottled a series of private-label whiskeys that have since become legendary. Among them is this bottle from 2003, which he created for Blue Smoke, a BBQ restaurant in downtown Manhattan. With its red background and bold typefaces, it is easily the most distinctive label Van Winkle ever produced.
Willett Family Estate Single Barrel Bourbon 28 Year Old 128.8 Proof 
Estimate: $10,000 – $15,000 

Pacific Edge, a wine and spirits shop in Agoura Hills, California, was an early and ardent fan of the Willett Distillery’s Family Estate program. Barrels they selected would be bottled with a standard Willett label, with the details about proof, age and customer filled in by hand (at first). Because the shop got in early, it was able to purchase unbelievable barrels, like this 28-year-old bourbon.
Old Rip Van Winkle 25 Year Old Decanter 50.0 abv
Estimate: $20,000 – $30,000 

At 25 years, this is the oldest Van Winkle whiskey ever released – the “Pappy of Pappys,” it’s called, not only because of its unmistakable flavor profile but because it is by far the best, rarest, most coveted bottle the Julian Van Winkle III has ever produced. It appeared in 2014, and only 710 were made. The wheated bourbon inside comes from Stitzel-Weller and is some of the last the distillery made before closing down in 1992. The bottle comes in a wooden box with an accompanying crystal stopper, made by Glencairn. This is pure, unadulterated bourbon luxury, in a bottle, and well worth every penny one pays for it.
A.H. Hirsch Reserve 15 Year Old 95.6 Proof 1974
Estimate: $5,000 – $7,000 

This bottle ranks among the rarest bourbons ever produced. Its story began in 1974, when a Pennsylvania liquor executive named Adolph H. Hirsch ordered a run of bourbon from the Pennco Distillery, near Philadelphia. He later sold it to a Kentucky liquor retailer named Gordon Hue, who had it bottled by Julian Van Winkle III at his Old Commonwealth Distillery. They began in 1989 with 15-year-old whiskey, sealed in gold wax, making this bottle one of the very first released in what would become the most legendary runs of American whiskey ever.