Greg Daily, CEO of iPayment, is expecting to make a make a painful loss in coming months. After losing a legal battle with investor David Shooker over Daily's manoeuvres to prevent him gaining a majority stake in the business back in 2000, Daily has filed for bankruptcy.
If and when this is granted, it will cost him his wine.
World renowned critic Robert Parker described the former wine: "The 1959 is unquestionably the greatest Lafite-Rothschild that has approached full maturity".
Wine investment remains big business with Christie's reporting auction sales of $50.6m in 2008 including a single owner collection that went under the hammer at $8m.
But Mr Daily seems to be a lover of wines rather than a straightforward investor.
The first evidence of this is in articles written by his friend and fellow businessman Tom Black, who collects and writes about wine and refers to their shared love of it. The second is the influence of personal taste on the cellar.
Daily placed a large order for Shiraz from the Australian Greenock Creek Vineyard last year. A bottle of this sells for around $600 - a lot to spend if you're having a glass with your lasagne, but not in the league of the others mentioned.
Indeed one of the wine's distributors described it as "quite hairy and feral", but Daily clearly loves it, as his shipment weighed in at 370 pounds.
Or perhaps if you're about to have $300 million in damages awarded against you, a hairy and feral wine is just what you feel like drinking.
Andrew Davison, an investment manager of the Vintage Wine Fund says rare wine is "... basically a low-correlation good absolute return commodity."
If and when the auction goes ahead, (it's expected to be in a New York auction house) the top end wines are expected to be a worthy investment.