What does "Five on Sixteen" mean?

“Five on Sixteen” is a paraphrase of a line from a Ray Charles song called “Blackjack”.

I sat there with two tens
I thought I’d have some fun
The dealer hit sixteen with a five
Just enough to make twenty one
Hey hey hey yeah yeah
How unlucky can one man be?
I find that to be a fitting metaphor for what happened on April 15, 2011 (now being called poker’s “Black Friday“) to the online gambling industry.  Some of the owners/founders of PokerStars, Full Tilt Poker and Absolute Poker/UltimateBet, three of the largest Internet poker companies operating in the United States, were accused of tricking regulators and banks into processing billions of dollars of illegal Internet gambling proceeds.
The timing couldn’t have been more surprising to those who follow developments in this industry. All signs had been pointing to imminent legalization of online gambling (or at the very least online poker) in the US. For example, state legislatures in New Jersey, Florida and California have recently considered bills on the subject, and the District of Columbia has officially legalized gambling online. The Nevada Gaming Commission recently struck a collaboration deal with the Gambling Control Commission in the online gaming friendly country of Alderney – a move many viewed as paving the way for legal online gambling in Nevada. Land-based casino companies had begun forming partnerships with popular online gaming companies (such as Wynn’s deal with PokerStars). The online gambling industry was holding two tens and poised for a big win against the US government’s sixteen, when suddenly the five came off the deck and sent the entire worldwide gaming industry flying sideways.
The business, legal and strategic landscape of online gaming changes as quickly and unpredictably as any industry out there. That’s one reason why it’s so challenging and enjoyable to counsel companies that operate in this space.

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