From 1993 to 1995, Simmons served as the director of communications at Humana Health Plan. In 1995, he met McConnell while waiting for an elevator at a Louisville, Ky., hotel after a speech his future boss made that day.

Top McConnell Aide

Simmons quickly became a key player in McConnell's office. In 1996, he ran the senator's successful reelection campaign, and in 1998, McConnell lent him to then-Rep. Jim Bunning (R-Ky.) to run his Senatorial campaign. In 2000, Simmons worked as deputy political director to then-Texas Gov. George W. Bush's presidential campaign. He worked at Bush headquarters and was on the ground in Florida to help ensure a Bush victory during the protracted recount.

After the 2000 race, Simmons worked with the Bush transition team, helping, among other things, McConnell's wife, Labor Secretary Elaine Chao, assemble her staff. He was offered a job in the Bush administration, but he instead decided to join Quinn Gillespie and Associates, a bipartisan lobbying firm. "My primary interest was to try a different aspect of the Washington experience," Simmons said.

In 2002, Simmons returned to McConnell's staff and has been the senator's top aide ever since, working in the majority whip's office until the Republican became the Senate minority leader after the 2006 elections.

Simmons is described as reserved. He is "old school, in the best sense of the phrase. He believes it's not about him," said Ed Gillespie, former Republican National Committee chairman and a former colleague at the lobbying firm Quinn Gillespie and Associates.

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