ST. PETERSBURG — As a lobbyist-turned-congressional candidate, David Jolly has repeatedly been attacked by Democrats who say he pushed for oil drilling off Florida's coast and represented a client who wanted to privatize Social Security — politically toxic issues in Florida.Jolly says his opponents are flat wrong. But a review of records and interviews show the truth is at least more nuanced and raises new questions about the Republican's role with a little-known conservative group that hired him to advance its interests in Washington.The group, Free Enterprise Nation, was founded by St. Petersburg businessman James MacDougald, who has quietly become a major campaign donor in Florida and is co-chairman of Jolly's finance team.A few years ago, MacDougald hired Jolly to be his point man on Capitol Hill, and Jolly's work has come full circle as he runs against Democrat Alex Sink and Libertarian Lucas Overby in a contest to replace the late Rep. C.W. Bill Young in Pinellas County's Congressional District 13.Lobbyists rarely run for elective office and when they do, their advocacy provides ammunition for opponents and exposes conflicts between what they were paid to do and what they may personally believe. For Jolly, those complications often lead to his work for MacDougald.MacDougald is not well known but has big ideas. He wrote a book called Unsustainable: How Big Government, Taxes and Debt Are Wrecking America.MacDougald argues for serious changes to Social Security and private pensions. Among his solutions: Turn Social Security into a "defined contribution" plan for anyone under 50, which would change the current system of a defined monthly paycheck.In an interview with the Tampa Bay Times, Jolly said he does not agree with that approach and that everyone who qualifies for Social Security vesting now should have their benefits guaranteed. The reports he must file on his work as a lobbyist only vaguely refer to "Social Security reform," which he said had to do with making clear the entitlement program's role in the national debt.In another instance of blurred lines, Jolly blogged for Free Enterprise Nation to keep readers abreast on plans to make military veterans pay more for health care — a politically dicey issue — and referenced "FEN conversations with appropriations committee staff," suggesting he played an active role.Yet in an interview Jolly bristled at the suggestion he supported higher costs for veterans, or lobbied the issue.As for oil drilling, Jolly said those questions are simply the result of his being careful. He said he listed the name of energy legislation on his lobbyist disclosure form merely because it came up in conversation. That explanation, and others like he has made, has some experts doubtful."I think he's trying to make a little revisionist history here," said Lisa Rosenberg, a lobbyist for the Sunlight Foundation, a nonpartisan Washington group dedicated to transparency in politics. "I have never heard of anyone saying I over-complied by reporting extra issues I'm not really advocating for. This is a new one to me."The drilling issue was the first of several questions that have arisen since Jolly entered the race — many of them linked to Free Enterprise Nation and MacDougald.Last week the Democratic Congressional Campaign Committee accused Jolly of lobbying for an "extreme group that supports privatizing Social Security" — even though the group's founder calls that a distortion."All they're doing is keeping (Sink) under wraps and letting the DCCC hit me with outrageous and dishonest charges," he said, as he accused Sink of ducking debates. "I'm not going to confront these questions about lobbying that much further."The DCCC on Friday announced another TV ad attacking Jolly as a lobbyist.• • •MacDougald, 70, is a former vice president of Home Life Insurance Co. of New York and co-founded ABR Information Services with his wife. They moved from New Jersey to St. Petersburg in the 1980s, and later sold the business for millions. He has become a significant political donor, contributing some $270,000.MacDougald said that after retiring, he learned several things about government pensions, Social Security and other programs that shocked him.He said he discovered there is no law absolutely requiring the government to pay Social Security — and that if there were, the program's long-term liabilities would have to be included in the national debt. He said he learned public pensions have far more long-term liabilities than is generally known.He grew so concerned that he wrote his book in 2010 and began appearing on national television to discuss it. He also poured more than $1 million into Free Enterprise Nation, which he formed to push for more transparency in public pensions; to promote private business; and to make sure Social Security payments were guaranteed.Jolly said he does not subscribe to MacDougald's defined contribution approach for everyone under 50, which means the government would make a set contribution to workers, who then would have investment options. He said it's important to make sure Social Security stays solvent and pays up for everyone who has been vested in the system, which means people who have worked and paid in for 10 years. For others — such as people who have not yet entered the workforce — there should be a wide-open discussion on reforming the program. He said everything should be on the table, including private accounts in which workers make their own investment decisions, as well as the important role of Social Security as a safety net."Anybody that has an intellectually honest conversation knows we have to have long-term entitlement reform in order to balance the budget," Jolly said.MacDougald wrote in his book that the public sector can sometimes be "socialistic." He wrote: "Life is good in the public sector, the socialistic part of our economy, because someone else is paying for it." Jolly said he would not have use the word "socialistic" to describe the public sector.MacDougald said the reason he hired Jolly as a lobbyist was simple: "It was to get me in front of people I needed to talk to." And the reason he wanted to talk to members of Congress was "so I could convince them that we need transparency from every level of government."• • •But Jolly did more than make introductions, working for MacDougald over several years, first with the large firm Van Scoyoc Associates and then when Jolly opened his own lobbying firm Three Bridges Advisors. FEN paid $60,000 to Van Scoyoc and $30,000 to Three Bridges.Some of the questions facing Jolly are the result of the precision and the vagaries of lobbying disclosure reports. In some cases Jolly insists he noted an issue simply because it came up in a conversation. In others, he described lobbying on something so broad it's hard to know what he meant — for example, "Social Security reform" or "health care reform."In a 2011 disclosure on behalf of FEN he wrote under "specific lobbying issues" legislation called "A Roadmap for America's Energy Future," which included proposals to expand oil drilling in the Gulf of Mexico.But Jolly says that he put it there out of abundance of caution after the legislation arose in a conversation. Jolly said he supports the current oil drilling ban in the eastern Gulf of Mexico and supports oil exploration in the central and eastern Gulf. MacDougald said his group supported the Roadmap for America's Energy Future but that Jolly was not paid to lobby for it.Jolly also listed that he lobbied for Free Enterprise Nation on the Paycheck Fairness Act, which Democrats have unsuccessfully pushed for in an attempt to get employers to pay women more. Jolly said he could not remember working on the issue but in an interview said he personally opposes it. But Jolly's report contains a very explicit mention of the issue. "I'm sure it's something that we talked about. I can't recall five years or four years ago what the conversation would have been," he said.Then there is the military health care issue. In a December 2010 blog post, Jolly also wrote about a plan to require military veterans to pay more for their government subsidized health care, a politically sensitive issue. Jolly said he did not lobby for the issue. "Find in there anywhere where I'm stating a position on Tricare or Free Enterprise Nation is," he said.In the blog post he wrote that then-Secretary of Defense Robert Gates has "continued to demonstrate honest leadership in addressing the unsustainable formulas that dictate the department's health care program." Jolly writes that "In FEN conservations with appropriations committee staff earlier this year, it is apparent that the committee has heard the secretary's message loud and clear." Is that lobbying? "Anybody who suggests that that paragraph suggests I was lobbying on Tricare is being intellectually dishonest," Jolly replied in an interview.