Newt Gingrich is giving his opponents a run for their money, but some are questioning whether social conservatives — a group Gingrich desperately needs to win the candidacy — can overlook his oft-controversial political and personal baggage.

Gingrich’s Washington insider label may not be that easy to shake off. The former House speaker has spent more than 20 years in Congress, and the last decade building up small business enterprises with close ties to politicians. His personal life has taken just as much heat as his political record.

Here’s a look at some of Gingrich’s past that continues to haunt him.

Ties to Freddie Mac

Gingrich made more than $1.6 million consulting for federally-backed mortgage giant Freddie Mac for eight years. That work would not have been scrutinized, except that Gingrich still hasn’t answered all the questions that have emerged about his affiliation with a group loathed by the right.

Most conservatives, including Tea Partiers, want Freddie Mac to be eliminated altogether.

Even Gingrich has turned on the group he once consulted for and advocated disbanding the group. He has blamed Freddie Mac and Fannie Mae for distorting the home loan market and demanded in 2008 that President Obama and other members of Congress return the money they received from Freddie Mac and Fannie Mae. More recently, he said Democrats like Rep. Barney Frank should be jailed for having ties with lobbyists at those organizations.

As for his own ties, Gingrich said he advised the organization to restructure their business and “suggest a totally different model” but sources inside Freddie Mac told Bloomberg that Gingrich neither predicted the housing bubble nor did he raise concerns about the business model.

Marriages

As he has done so in his past campaigns, Gingrich has made family values a core focus of his presidential run. But he cannot escape what he has admitted are shortfalls in his own family life.

Gingrich, who was dogged by allegations of extramarital affairs early in his career, has had two failed marriages.

He married his second wife, Marianne, the same year his divorce with his first wife was finalized. He then took up with his current spouse, Callista Bisek, while he was still married to wife No. 2. Even as he was reportedly having an affair with Bisek, a Congressional aide 23 years his junior, Gingrich was blasting Bill Clinton on his family values and his relationship with Monica Lewinsky.

He later blamed his busy political life for his inappropriate actions, telling the Christian Broadcasting Network that such things were “partially driven by how passionately I felt about this country, that I worked far too hard.”

In recent years, Gingrich and Callista racked up to half a million dollars’ worth of debt at Tiffany’s. Gingrich’s financial disclosures revealed that his wife held a revolving charge account at Tiffany and Co. in 2005 and 2006, when she worked at the House Agriculture Committee. Their liabilities at the jewelry store ranged from $250,001 to $500,000 over time.

The two were also lambasted over the summer for going on a cruise in the Greek Isles at a time when some of his staff thought they should have been focusing on the campaign. That trip, in part, led to the mass resignation of many of the campaign’s senior leadership, who said Gingrich was not focused on the election.

Religion

Gingrich’s religious affiliation may not bring the same kind of media attention as Mitt Romney’s Mormonism,  but it’s still a point of discussion in conservative circles.

Influenced partly by his wife, Gingrich converted to Catholicism in March 2009. The move was welcomed by many in the Catholic community, but others asked whether it was merely a political ploy by a man who had had an extramarital affair and two failed marriages.

Though the United States has had only one Catholic president — John F. Kennedy — the Catholic connection could help Gingrich in the general election. Catholic voters, who had favored Democratic over Republican candidates by double-digit margins in the last two congressional elections, swung to the GOP in 2010, according to an analysis by the Pew Research Center.

It wasn’t the first time Gingrich switched denominations. He was born into a Lutheran family, but became Southern Baptist when he was in graduate school.

Immigration

Gingrich has presented the most moderate stance on immigration among Republican contenders, which could both help or hurt him in the primaries.

The former House speaker said he advocates a “humane” immigration policy, which includes a path to legalization for people who have long-established family roots in America. His opponents have slammed his ideas as providing amnesty to illegal residents.

Some say the idea is unlikely to sit well with conservative voters, who want to tighten immigration laws and support such measures at the state level.

But others say the move could help Gingrich pick up Latino voters, a demographic that George W. Bush successfully courted. That group, however, will be more influential in the general election than in the primaries and caucuses.

Global Warming

In 1989, Gingrich co-sponsored the Global Warming Prevention Act and in 2008 appeared with then-House speaker Nancy Pelosi to warn about global warming. Now he says he doesn’t know whether climate change is really occurring and called that ad “the dumbest single thing” he’s done in recent years.

Gingrich may be walking back from his comments but it remains to be seen whether conservatives can overlook his past stance.

He also once advocated imposed mandatory limits on carbon dioxide emissions, but has recently become a vocal critic of the cap-and-trade bills.

“I do know that I’m opposed to cap-and-trade and I’m opposed to any kind of massive government response,” he said recently.

Health Care

Even though he assailed the health care bill, Gingrich once advocated an individual mandate for insurance coverage.  He has been accused of having close ties to insurance giants through his businesses.

He has blasted the individual mandate in the Affordable Care Act, saying in a video that he is “completely opposed to the Obamacare mandate on individuals,” and that he “fought it for two and half years at the Center for Health Transformation.” But the Center for Health Transformation, which Gingrich founded, actually supported imposing a mandate on those who made more than $50,000 per year. Gingrich himself has said that individuals have a responsibility to have health insurance.

The group says it advocates such a move at the state level, not solutions that are “forced at the federal level,” but that hasn’t been clear through Gingrich’s past statements. In fact, he criticized opponent Mitt Romney for implementing such a “bureaucratic” mandate in Massachusetts.

Gingrich also broke from the right when he praised his client Gundersen Lutheran Health System’s end-of-life best practice as one that “empowers patients and families.” At the height of the health care debate, in which end-of-life care became a key dividing issue between Republicans and Democrats, Gingrich stood alone in the Republican field.

Abortion

Some Republicans are concerned about Gingrich’s changing views on abortion and whether he’s sincerely conservative on this issue.

Gingrich has said he supports abortion in the case of rape, incest and if the mother’s life is in danger. Although he now opposes federal funding for embryonic stem cell research and abortion, he didn’t always think that way.

In 1995, Gingrich supported a measure to provide federal funding for abortion to poor women who were victims of rape or incest. In 2001, Gingrich said stem cell research on embryonic cells that are “pre-fetal” isn’t objectionable.

Child Labor

In the latest flap to engulf the former congressman, Gingrich is taking heat for calling U.S. child labor laws “truly stupid.”

Speaking at Harvard’s Kennedy School of Government, Gingrich blasted unions and suggested that in poor areas, children should replace janitors.

“It is tragic what we do in the poorest neighborhoods, entrapping children in, first of all, in child laws, which are truly stupid,” Gingrich said.  “Most of these schools ought to get rid of the unionized janitors, have one master janitor and pay local students to take care of the school. The kids would actually do work. They would have cash, they’d have pride in the schools, they’d begin the process of rising.”

Gingrich later explained that he wasn’t advocating looser child labor laws or saying that children should drop out of school and become janitors, but suggesting ways in which young teens could become “empowered to succeed.” Still, his comments have sparked national furor.

The American Federation of State, County and Municipal Employees launched an online petition denouncing Gingrich’s ideas as “vicious and wrong.”

Liberals have blasted Gingrich’s remarks as “truly stupid.”

His comments, however, have brought virtually no response from conservatives.