Betting on Red

Under any other circumstances, a federal case over the possessive "s" wouldn't seem like a big deal. But when it pits Larry Klayman—a gadfly lawyer best known for digging up dirt on the Clintons during the 1990s—against a cadre of high-powered Bush allies,well, things can get interesting. Those who still remember Klayman grilling Clinton aides in pursuit of Filegate may have felt a touch of schadenfreude in November as he deposed the likes of ex-White House flack Ari Fleischer. But Klayman's latest legal crusade could create real headaches for his target—Freedom's Watch, a new conservative nonprofit (where Fleischer is a board member) with big ambitions for the 2008 election.

On the surface, Klayman's suit is about whether Freedom's Watch is treading on his rights to the name Freedom Watch, which he registered a few years ago. ("They picked the wrong guy to steal a trademark from," he boasts.) But Klayman—notorious for suing even his own mother—also aims to unravel some of the group's mysteries, such as the true depth of its coffers and the extent of its ties to the Bush administration.

Key to unlocking these secrets may be another man Klayman hopes to depose: casino mogul Sheldon Adelson, the group's top donor, who is shaping up as the right's answer to George Soros—only a lot richer. Last year, Forbes pegged Adelson as America's third-wealthiest person, with a net worth around $28 billion. Even a sliver of that fortune will go a long way for Freedom's Watch, which is expected to barrage would-be voters with ads on foreign policy, national security, and domestic issues. Freedom's Watch hopes to direct as much as $200 million into the 2008 campaign, nearly 10 times what Swift Boat Veterans for Truth spent in 2004. "Money won't be an object," promises Matt Brooks, Freedom's Watch's treasurer.

The group's pedigree includes tight connections to the Republican Jewish Coalition (or rjc, where Brooks is executive director) and the American Enterprise Institute (aei). Closely allied with the party's ultra-hawkish Cheney wing, the group was conceived in part to counter MoveOn.org and help the administration sell its Iraq policy. Among its donors are elite gop fundraisers such as Florida developer and former ambassador Mel Sembler and evangelical philanthropist John Templeton Jr., but sources say Adelson has been the most generous.

Freedom's Watch began strutting its stuff late last summer with a $15 million national ad blitz to bolster support for the troop surge. The TV spots feature pleas from wounded soldiers and families of the dead. In one, a grieving mother concludes, "We've already had one 9/11. We don't need another." Other ads take direct aim at "radical liberal group" MoveOn for its "despicable" criticism of General David Petraeus and at Iran's "terrorist" president, Mahmoud Ahmadinejad.

Iran is high on the group's agenda. In mid-October, Adelson and other key donors spent two days at a private Washington forum on radical Islam and the "Iranian threat," a hush-hush Freedom's Watch project aiming to lay the groundwork for a more aggressive U.S. policy toward Tehran. (aei scholar Michael Ledeen, who was there, says Adelson urged the assembled activists and conservative terrorism experts to work together, stressing that his group had ample cash for projects in these areas.) The day before, Adelson had been part of an rjc gathering where the major gop candidates competed to demonstrate their tough stance toward Iran; Rudy Giuliani, for whom Adelson had earlier hosted a fundraiser in Las Vegas, emerged as the clear favorite.

Born in 1933 in Boston, where his Lithuanian immigrant father worked as a cab driver, Adelson built his fortune with the same take-no-prisoners ambition that characterizes his approach to politics. After dropping out of City College of New York, he tried his hand as a court reporter and mortgage broker. Then, in 1979, he launched Comdex, which became the computer industry's biggest U.S. trade show, and which he sold in 1995 in a package deal worth $862 million. Along the way he built his casino empire, starting with the old Sands Hotel and Casino, which he bought in 1989, tore down, and replaced with the lavish Venetian casino and Sands convention center. "Most of the hotel casinos were worried about filling their rooms on the weekends," says a fellow gambling exec. "He concentrated on Monday, Tuesday, and Wednesday nights and the convention business."

Adelson is also strongly antiunion, which doesn't play so well in Vegas, and is known to be quick with a lawsuit. "He's probably one of the most litigious people on the planet," says John Wilhelm, a leader of Unite Here, a union that represents hotel and casino workers.

Adelson was already a member of the billionaires club when he took his company public late in 2004, boosting his net worth nearly $6 billion in a single day. He spent $265 million that year opening a Sands casino in Macao, a special administrative region of China, made his money back within 12 months, and opened the even ritzier Venetian Macao last summer. Another $3.5 billion casino venture is set to open in Singapore next year.

All this wealth has fueled Adelson's political and philanthropic projects. He gave Holocaust history group Yad Vashem $25 million in 2006, and this past summer fronted a rumored $180 million to launch Yisrael Hayom, a free daily newspaper based in Tel Aviv. Along with his wife Miriam, an Israeli-born physician, he also set up a charitable foundation to distribute $200 million annually to causes including Taglit-Birthright Israel, which introduces young Jews to the homeland via all-expense-paid trips. Sources say Adelson is a key backer of an American Israel Public Affairs Committee offshoot that organizes similar trips for legisla­tors. Steve Grossman, a longtime friend who has helmed both the Democratic National Committee and aipac, recruited Adelson as an aipac donor in the 1980s and says the casino magnate is an "ardent supporter" of Likud Party chairman Benjamin Netanyahu.

Adelson is also a fan of George W. Bush, having attained Pioneer status by pulling in at least $100,000 for the president's 2004 reelection campaign. In 2006 he kicked in $1 million to help Newt Gingrich launch his new 527 committee, American Solutions for Winning the Future. And veteran fundraisers insist Adelson brings more to a cause than his checkbook. "I found him to be a very good adviser and a very smart strategist," says Ken Mehlman, a former Republican National Committee chair and current rjc board member who is an outside adviser to Freedom's Watch.

The coming months should offer a fuller picture of Adelson's strategy at work. Freedom's Watch aims to become a Johnny Appleseed of the national conservative movement, leveraging its influence by funding grassroots groups on issues such as free markets and the drug war. The election is merely a first stop: Former White House scheduler Brad Blakeman, the group's president, noted recently that the organization envisions a "never-ending campaign."

As long as Adelson is on board, that's not a bad bet.