History often does more than make great tasting wine (and just what is the best bottle of wine you will ever drink worth to you?), it makes for unbelievably competitive auctions in the wine arena, but it was an insurance company that valued Chateau Margaux 1787 that was authenticated as belonging to the wine collection of Thomas Jefferson and paid out at a cool $225,000. Paid out? William Solokin, the wine merchant who had it in his possession, appraised the irreplaceable wine bottle but when he brought it to a Four Season Hotel for a Margaux dinner the waiter dropped it! The insurance company paid out the quarter shy of a quarter million for the shattered bits, though he pined for a $500K payout or a one of a kind sip he would never taste.

Though estimated to sell for up to $60K each, the Chateau Lafite’s 1869 bidding war for the rare vintage resulted in a $230,000 for a standard sized bottle available at a Sotheby’s auction in Hong Kong in 2010. Though ancient, the wine was known to the collector who acquired all three of the three available 1869 bottles for a total of $690,000. This is the most anyone has been willing to pay for a standard sized bottle of vino, and the owner can slowly relish drinking the first two bottles while keeping the third to the envy of all.

Chiming in at number three is a bottle of champagne that was salvaged from a Swedish Freighter off the coast of Finland in 1998, the 1907 Heidsieck, which sold at numerous auctions and brought in as much as £163,000 (or $275,000 US). The kicker here, folks is that 2,000 of these bottles were recovered, but the story of the commissioned ship destined for the Imperial Court of Tsar Nicholas II of Russia that had been torpedoed by a German Submarine in World War I adds significant historical significance to the 100-plus year old flavor.

2. 1947 Cheval-Blanc | $304,375 (£192,000)*

The 1947 French Cheval-Blanc is widely recognized as the most expensive sold bottle of vino in history at $304,375 (see the next wine for the asterisk* explanation). In 2010, the 67-year-old bottle was sold to a private collector at a Christies auction in Geneva. According to the Classification of Saint-Emilion wine, the Cheval Blanc has a class A status [and] … of all the merlot wines, there are only two which were granted with this classification. The grapes were said to be legendary between April and October of 1947, and the survivor bottle that outlived many a person is the only known bottle in the Imperial format from this particular Saint-Emilion vintage.

1. Screaming Eagle Cabernet Sauvignon 1992 | $500,000*

The most expensive wine ever sold is the exception to the dated rule of rare wine, as it was not even a decade old at the time of purchase; the six liter Screaming Eagle Cabernet Sauvignon 1992 bottle sold for a whopping half a million bucks (that’s right, folks, $500,000) in 2000 at a Napa Valley charity auction! It was only available for a limited time in 1995, and apparently was the cat’s meow, at least to one wine connoisseur out there, because it is rumored Chase Bailey, a former Cisco Systems executive, picked this up, though we have an asterisk* here (unlike Major League Baseball’s home run record book), because the $500K bottle was knocked down a bit in price because it was a charity sale, although it could still have sold for more than any other wine in history.

When will we see a bottle of red go for the fabled one million dollars?