INDIAN SHORES — David Jolly made all the right moves to prepare for a congressional run in 2010.As one of the few people aware that U.S. Rep. C.W. Bill Young was preparing to retire after four decades, Jolly quietly and methodically began to line up supporters. He started appearing regularly at local GOP functions, schmoozing with local party leaders at their Crabby Bill's watering hole, donating thousands of dollars to the Pinellas GOP, and keeping then-U.S. House Minority Whip Eric Cantor abreast of his plans to succeed Young, his former boss.Young, Jolly said, summoned him to his home on Memorial Day 2009 to tell him he had decided not to run for re-election — and would like to see Jolly, his 36-year-old former aide and personal attorney, run for the Pinellas congressional seat. But then month after month and opportunity after opportunity passed without Young uttering another word about his plans.The fish-or-cut-bait moment came at the Pinellas Republican party's Lincoln Day Dinner in February 2010. While most people at the time were focused on a local "straw poll" vote between then-Republican U.S. Senate candidate Charlie Crist and upstart Republican Marco Rubio, Jolly waited intently for Bill Young's speech."I had two emails in my BlackBerry loaded up," Jolly recounted. "One said, 'Mr. Young announced his retirement tonight. It's time to honor him and respect him. I'm also announcing that I'm running for Congress.' And I had another email that said, 'Mr. Young announced tonight he's running for re-election. Please join me in supporting him.' "Young, of course, ran and won again in 2010 and 2012. When the 82-year-old congressman announced he would not seek another term in October, Jolly again was part of the inner circle who knew he might not live to finish his final term.Now, thanks largely to his political savvy and fundraising networks as a Washington lobbyist and former Young aide, Jolly is the ostensible Republican frontrunner to take on Democrat Alex Sink in the March special election. Jolly, 41, is far and away the most polished and best informed about key federal issues facing Congress compared to fellow Republican candidates Mark Bircher and Kathleen Peters. But it's not at all clear he's the strongest Republican to take on Sink, the former Florida chief financial officer who narrowly lost the 2010 governor's race to Rick Scott. State Rep. Peters derides Jolly as "another Washington insider" without deep Pinellas roots. Democrats will hang the "Washington lobbyist" label around his neck like an albatross if he's the nominee.Jolly, a soft-spoken lawyer who describes himself as normally "a very private person," is quick to note that lobbying these days is only a small piece of his overall income, and that his main job is as a vice president of Clearwater-based investment company Boston Finance Group.Still, as politically toxic as the Washington insider label may be, that experience is at the heart of Jolly's campaign message: He has the know-how, the relationships and the experience to hit the ground running."That experience is tremendously helpful," said Pinellas Republican Party Chairman Tony DiMatteo, who enthusiastically supports Jolly. "You basically have 435 lobbyists up there looking out for their own districts, and I want a first-teamer up there looking out for me. Bill Young was his mentor, and David is the best shot we have at trying to replace Bill Young."Jolly is a native of Dunedin, the son of a Baptist pastor, but has not yet shaken the suggestion by critics that he's more a product of Washington, D.C., than Pinellas County. He is defensive about this, and not entirely convincing when he tries to debunk the charge.He stresses that he has lived in Pinellas since 2005. (He owns a 950-square-foot condo in Indian Shores that he and his wife bought in 2005 for $340,000. They also own a 1,650-square-foot home in Washington bought in 2007 for $900,000).Jolly often notes that he serves on an Indian Shores zoning board (not a heavy lift considering that board has not met in three years).He says he served as Rep. Young's district director for a year. (Actually, it was more like seven months.)His cellphone number has a Washington area code. Since registering to vote in Pinellas in 2006, county records show he has voted by absentee ballot 10 times and in person three times.While Peters constantly refers to herself as a Pinellas soccer and Little League mom, Jolly has no children. He is separated from Carrie, his wife of 15 years, and said their amicable divorce will be finalized in Washington on Jan. 16, two days after the special primary election."He's a great guy, and I wish him well," was all Carrie Jolly would say to the Times.Jolly began as an entry-level staffer for Young in 1995 and eventually became his general counsel and part of his small band of top advisers, as well as his personal family attorney. He is smart enough not to imply he is entitled to inherit a congressional seat from Young, but the dozen years he spent working for the congressman are at the center of his pitch."We can't lose sight of the fact that we have to elect somebody on day one that can impact this community and has the ability to get things done, not just pontificate about national political issues and political philosophies," he said.Federal budget earmarks that Young so liberally showered on Tampa Bay may be a thing of the past, but Jolly said even a junior member of Congress can be effective at protecting and promoting spending programs that still fuel Tampa Bay's economy.When it comes to protecting federally funded defense and high-tech companies in Tampa Bay, for instance, Jolly says he would be a rare freshman who could immediately get a meeting with New Jersey Rep. Rodney Frelinghuysen, a longtime friend of Young's who heads the defense appropriations committee."I'm fortunate that I had an opportunity to work on issues important to Pinellas County with Mr. Young, and I understand those issues and have established relationships with key members of leadership," Jolly said. "I'm not saying the others wouldn't get there eventually, but there's always a big learning curve."Adam C. Smith can be reached at [email protected].