It was a beautiful summer evening in 2005 and Chicago's social scene was gathered at Japonais, the posh sushi restaurant along the Chicago River, for a fundraiser for Tsunami Foundation. The party was organized by promoter to the charities Jennifer Schwab, who became legendary in the scene by convincing macho men to don high heels and race around the United Center all in the name of charity. Tsunami Foundation offered youth mentoring programs in some of Chicago's roughest neighborhoods as well as college scholarships to deserving high school seniors. The guest of honor Rudy Fratto Jr, the recipient of Tsunami's latest scholarship, was a relatively impressive young man. He maintained a B average, starred on his high school's hockey team and kept up an impressive list of other extracurricular activities. Nevertheless, the choice of Fratto for a scholarship was peculiar for a couple reasons. First, his father is Rudy Fratto Sr., a reputed lieutenant in the Chicago Outfit, who would plead guilty to tax evasion in 2009 and subsequently also be charged with mail fraud in the spring of 2010. Second, at 14 years old, Rudy was still several years away from needing a scholarship. Celebrities like Jerry Azumah and Ozzie Guillen Jr. were at the shindig. Sarah Preston and Ted Widen covered the event for Chicago Magazine and Chicago Scene respectively. The socialite community was represented with guests like Austin Manzure, Anderson Bell, and Amanda Puck. Also in attendance was John "No Nose" DiFronzo, reputed boss of The Outfit. Even the advisory board of Tsunami Foundation was an eclectic mix of Chicago’s movers and shakers. It included the proprietor of Tsunami Foundation, Tony Demasi. Also on the board was AT&T executive and future Alderman Brendan Reilly. Another member of the board was “restaurateur” Joe Farina. It’s alleged that the restaurateur Farina is also connected to the Outfit. For Tony Demasi, the then-30-year-old Tsunami Foundation founder, it was a day in a life equal parts Entourage, Sopranos and Wall Street. Fundraisers like this put Demasi in direct proximity to his natural market for his new nightclub, Reserve, which he owns along with Tsunami Capital, an investment firm