Watershed moment: After eight previous defeats, Todd Gray, pictured with his wife, Ellen Kassoff Gray, finally took home the Chef of the Year award at the Rammys. (Courtesy of Todd Gray’s Watershed)

After eight previous defeats, Gray had his doubts and decided to turn his skepticism into a wager. “I’d be willing to bet you $100 that I won’t win,” Gray apparently told Hagedorn. “So we shook hands,” the chef told All We Can Eat this morning.

The chef lost the bet.

History aside, Gray certainly had reasons to doubt his chances this year. His competition for the 2011 chef of the year award included heavyweights Bertrand Chemel of 2941, Haidar Karoum of Proof, Vikram Sunderam of Rasika and Bryan Voltaggio of Volt.

Truth be told, it’s not like the Rammys, produced annually by the Restaurant Association Metropolitan Washington, have been all that bad to Gray and his team. Equinox won the best new restaurant award in 2000. The restaurant’s Lisa Scruggs took home the pastry chef award in 2002, and Gray’s wife and business partner, Ellen Kassoff Gray, won manager of the year in 2007. Equinox itself won best fine dining restaurant in 2008.

But until his name was announced last night at the Marriott Wardman Park Hotel, Gray thought he might have been snakebit or at least the victim of the complicated politics that may or may not underlie the Rammy voting. (The Rammy judges are anonymous and the voting process opaque, leaving chefs and managers and other nominees to wonder on what basis winners and nominees are actually selected.)

“After a certain time...you have to wonder what’s going on,” admits Gray, who has lost the chef of the year title so often that he thought this was his 10th nomination instead of his ninth. “You’d think the fourth or sixth or seventh or eight time is the charm. I had to wait to 10.”

The chef was so unprepared for the victory, he didn’t write a speech. Gray just went to the podium accompanied by his son, Harrison. Ellen Kassoff-Gray didn’t want to go onstage. “She wanted me to go up alone with Harrison,” Gray says. “It was a great feeling and, as always, I couldn’t thank enough people.”

Gray has yet to settle the bet but figures that since Hagedorn is helping the Equinox couple with their planned cookbook, tentatively titled “Kitchen Conversations,” the chef will just roll the Benjamin into the next payment. “I will gladly pay him the $100 now,” Gray says.

Contacted earlier today, Hagedorn swears he didn’t have any insider knowledge that Gray would win. He’s not a Rammy judge, he says. He also declined to take the chef’s money on what was, essentially, a friendly wager.

“I told Ellen to write a check to the Humane Society,” Hagedorn told AWCE. It’s an organization close to Kassoff Gray’s dog-loving heart.

Here’s the full list of winners from last night’s Rammys:

Duke Zeibert Capital Achievement Award: Jose Andres

Chef of the Year: Todd Gray, Equinox/Watershed

Fine Dining Restaurant: The Source by Wolfgang Puck

Upscale Casual Restaurant: Tabard Inn

Best New Restaurant: Estadio

Rising Culinary Star: Kyle Bailey, Birch & Barley

Pastry Chef: Tiffany MacIsaac, Neighborhood Restaurant Group

Restaurant Employee: Ryme Lansari, Cafe Atlantico and Minibar

Restaurant Manager: Hans Olson, Clyde’s of Reston

Wine Program: Taberna del Alabardero

Beverage/Mixology Program: Founding Farmers

Joan Hisaoka Associate Member of the Year: Ritz-Carlton

The People’s Choice Awards

Neighborhood Gathering Place: Ted’s Bulletin

Power Spot: Carmine’s

Hottest Bar Scene: Chef Geoff’s Tysons

Your Favorite Restaurant: Carmine’s

Where Magazine Visitors’ Choice Award: Old Ebbitt Grill

This post originally ran in All We Can Eat