Senator John McCain was on a roll. In a room reserved for high-stakes gamblers at the Foxwoods Resort Casino in Connecticut, he tossed $100 chips around a hot craps table. When the marathon session ended around 2:30 a.m., the Arizona senator and his entourage emerged with thousands of dollars in winnings.

The problem?

According to a non-partisan government watchdog, McCain never reported the winnings from this and other gambling excursions in his annual financial disclosure statements, as required by federal law and Senate rules.

Citizens for Responsibility and Ethics in Washington (CREW) filed a complaint today with the Senate Ethics Committee, calling for an investigation into whether McCain, reportedly an avid gambler, broke the law. You can view the complaint here (PDF). From a CREW press release:

The Senate Ethics Manual states that winnings, such as those derived from a lottery or a game show, are gifts that must be reported as income. Knowingly filing a false report is a crime punishable by up to five years in jail.

Nevertheless, Sen. McCain reported no income derived from gambling on the personal financial disclosure reports he filed with the Senate between 2000 and 2007.

In contrast, other members of Congress, including Sen. Judd Gregg (R-NH), House Minority Leader John Boehner (R-OH) and Rep. Paul Kanjorski (D-PA) all reported winnings on their financial disclosure reports.

CREW’s executive director Melanie Sloan stated, “Given Sen. McCain’s long history of gambling, the fact that he never included gambling income on his financial disclosure forms suggests he is either the unluckiest gambler ever or, more likely, he failed to report the income.”

Presumably, a failure to report his winnings to the IRS would also be problematic, as all gambling income is fully taxable.

Obviously, I don’t know if McCain won any money, but a quick look at Line 21 on his 2006 and 2007 tax returns — available on his campaign Website — reveals that he did not report any “other income” in either year.

I’d suggest the IRS look into the matter, but I’m afraid I’d be risking a Nixonian “random audit” should McCain win in November.

Teeing off a New York Times article detailing McCain’s ties to lobbyists for the gaming industry, Obama said craps is fine, but friends don’t let friends bet on Bush:

I read the other day that Senator McCain likes to gamble. He likes to roll those dice. And that’s ok. I enjoy a little friendly game of poker myself every now and then. But one thing I know is this – we can’t afford to gamble on four more years of the same disastrous economic policies we’ve had for the last eight.

I know that when Senator McCain says he wants to bring the same kind of deregulation to our health care system that he helped bring to our banking system – his words – well, that’s a bet we can’t afford. We can’t afford to roll the dice by privatizing Social Security, and wagering the nest egg of millions of Americans on Wall Street. We can’t afford to gamble on more of the same trickle down philosophy that showers tax breaks on big corporations and the wealthiest few. We’ve tried that. It doesn’t work. With our economy at risk, and our future in the balance, the greatest risk in this election is to repeat the same mistakes of the past. We can’t take a chance on the same losing game (prepared remarks).

The gambling angle is the Democrats’ official attack today. The DNC cut a new web ad arguing that McCain’s gambling ties show he is indebted to “special interests,” as I wrote earlier.

Obama also dredged up some of McCain’s reality-defying remarks about economics. Reminding voters that McCain once implied that deregulation helps grow the economy, Obama was incredulous. “Senator, what economy are you talking about?” he asked.

As the bailout package flounders on Capitol Hill, however, the most pressing issue is not past remarks by McCain. Voters and members of Congress are sour on the proposed bailout. Will either candidate will move beyond rhetoric and lean into the buzz-saw, rallying their caucus behind the package that they both said they support?

Obama will likely raise the issue while campaigning in Colorado today, predicted the aide, in response to a New York Times article detailing McCain’s ties to lobbyists in the gaming industry.

The attack looks like a priority for Democrats this week. The DNC is launching a new web ad, “Betting on McCain,” contending that the lobbyist revelations show that McCain is driven by “special interest politics.” It will run on news, political and religious websites. Democrats say the ad demonstrates:

John McCain’s history of stacking the deck in favor of his favorite gambling industry lobbyists. The video comes on the heels of a new report outlining McCain’s pattern of using his position as the chairman of a key Senate committee to tip the scales in favor of casino lobbyists with connections to his family and campaigns — even if it meant reversing long held positions.

After campaigning in Colorado today, Obama makes his own trip to gambling country — with stops in the swing state of Nevada tomorrow. He often recounts how he outlined his reform plan for the auto industry in Detroit — we’ll see if he brings that same confrontational approach to criticizing gambling.