Along the way to becoming one of the city's most influential figures, politically wired attorney Willie Shepherd bullied, belittled, lied, and then some. And his fellow partners at Kamlet Shepherd & Reichert failed to stop him until two junior attorneys took a stand.
At lunchtime, according to former employees, it was not unusual for Wille Shepherd to plop his 300-pound frame into a chair at the conference table in his office and dig into a meal big enough for two people. He favored the Capital Grille and would have an underling fetch a take-out order that would look like two steaks, a side of something, and a bowl of French onion soup. Often, he insisted that his two assistants join him. In his view, according to several former KSR employees, such companionship, along with unflinching loyalty, was part of what subordinates were paid for. Shepherd tended to talk as he chewed, spraying spittle and dropping food from his mouth. It was not unsual for him to want an afternoon snack, and he would occasionally send someone to Johnny Rocket's to pick up a hamburger and French fries. Toward the end of 2007 and into 2008, Shepherd had a voracious appetite, for many things.
As Staks and Almon were discovering what struck them as Shepherd's ethical violations in early 2008, the city was transforming itself for the Democratic National Convention. So, too, was Shepherd. He wanted to present himself as someone worthy of a position with the presidential candidate's team of advisers, and ultimately worthy of a spot in the Obama administration. He had been telling colleagues that what he wanted was a Cabinet seat, ideally secretary of energy.
To improve his public profile, Shepherd had become the city's Convention Host Committee finance chair, and promised to raise $150,000 for the Obama campaign's Obama For America (OFA). To help with the fund-raising obligations and the coordination of related events, Shepherd had felt it necessary to marshal more resources. He hired a second assistant. To a Stephanie Wilson, he had added a Stephanie Estabrook. Some of Shepherd's colleagues only half-jokingly observed that with two assistants he was even harder to reach. Wilson primarily handled Shepherd's traditional workload, and Estabrook and the firm's marketing manager, Terri Taylor, aided with convention-related endeavors.
Shepherd always seemed to be running here and there, meeting with this CEO and that tycoon for the fund-raising. But, according to several sources involved with his convention activities, he often left it to others to do the work. During a trip to D.C., according to a well-placed source, Shepherd missed a morning meeting with potential corporate donors, leaving his underling, Taylor, and a staffer from Senator Ken Salazar's office to make nice. As the deadline for OFA approached, it became evident that Shepherd was well short of raising $150,000. According to sources familiar with the fund-raising, it was Shepherd's relatively new hire, the twentysomething Estabrook, who would regularly make calls to potential donors; she was the one left to forge relationships with the OFA grassroots team and to work with them to "find" anonymously made donations that could be credited to Shepherd. None of that, according to a Denver-based Obama campaign worker, prevented Shepherd from prominently featuring his name on the promotional materials for a party for donors, which, the source says, angered Bruce Oreck. Now the U.S. ambassador to Finland, Oreck made his fortune in the family's vacuum cleaner business and had sucked in at least $500,000 for OFA.
While Shepherd was aggressively trying to beef up his public persona, he decided to undergo gastric bypass surgery. He walked into the office of a KSR administrator, and, according to the now former administrator, announced his desire to have the procedure. He was expecting the firm's insurance company to cover the cost, the former administrator says, and when he was informed that there was a process for such surgeries—and even then it likely wouldn't be covered—Shepherd berated her. According to the former firm administrator, Shepherd screamed at her, "I founded this firm. I built it up from nothing." In the end, according to the former administrator, KSR's insurance plan did not pay for the surgery. Before the procedure, it was big meals from the Capital Grille and Johnny Rocket's; after the surgery, Shepherd's diet included yogurt and black beans.
Considering the convention chaos, Staks and Almon decided that this was no time to voice their concerns about Shepherd. No one, they concluded, would have time to listen to, or want to hear, what they had to say about the firm's chairman and managing partner, the finance chair of the Convention Host Committee, a fund-raiser on OFA. Truth be told, the two attorneys hoped that Shepherd would get a plum political appointment and would be out of the firm, and out of their lives, forever.