When Mitt Romney was a young man, his father gave him direct advice: “He said never get involved in politics if you have to win election to pay a mortgage,” Romney often says. “Financial independence was key.”

The son followed this advice so successfully that he made a fortune, retired in 1999, turned to public service and has never taken a salary since.

But the wealth intended to liberate Romney the politician instead has ensnared him. He hoped it would free him; for many voters, it now seems to define him.

Democrats have relentlessly cast him as a corporate raider and out-of-touch plutocrat. And Romney, after more than a year running for president, has made one comment after another that inadvertently reinforces those characterizations.

“Why don’t you stick up for yourself?” a high-dollar donor asked Romney at the private fundraiser that was secretly recorded and leaked this month. “To me, you should be so proud of your wealth. That’s what we all aspire to be. . . . Why not stick up for yourself and say, ‘Why is it bad to be, to aspire to be wealthy and successful?’ ”

Romney paused and launched into a two-minute description of what he tries to get across on the stump, “the fact that people who dream and achieve enormous success do not make us poorer — they make us better off.” But he never answered the question.

His oldest son, Tagg, offered one explanation for his father’s reticence in an interview Friday. “He was taught that when you do good things, you don’t brag about them.”

Three days before the first presidential debate, seen by some as Romney’s best or even last chance to sell himself, the persistent focus on his riches has taken a deep toll on his image, a battery of recent polls suggest.

By 2 to 1, registered voters in a late August Washington Post-ABC News poll said that Romney would do more to help the wealthy than the middle class. The numbers were flipped for President Obama, with more than twice as many voters saying he would prioritize the middle class over the wealthy. In another measure of trust, registered voters in Ohio, Florida and Virginia gave Obama double-digit margins over Romney when asked which candidate understood the economic problems that Americans are facing, according to Post polls this month.

Money, culture entangled

Americans have elected many rich elites as president, starting with George Washington. But Romney’s wealth, estimated to be between $190 million and $250 million, is inextricably bound up with two cultures that are mysterious and misunderstood by many people: high finance and the Church of Jesus Christ of Latter-day Saints.

He also has a complicated relationship with his own money, which he has been unwilling or unable to explain to the public. One day he says he won’t apologize for his success; another day he jokes before a roomful of donors that he’s “poor as a church mouse.”

In one year, he and his wife, Ann, gave away far more money — $4.2 million — than most Americans will earn in a lifetime, according to the 2011 tax return he filed two weeks ago. But he has resisted calls to release more tax returns, citing a wish to keep his charitable contributions private as one reason. “It’s a very personal thing between ourselves and our commitment to our God and to our church,” he told Parade magazine.

Staggering success and fear of failure; pride and modesty; high-ticket purchases and penny-pinching make-dos; generosity and penury all exist side by side in the way Mitt Romney regards his own stockpile of money, say friends, family and business associates.

His admirers long ago gave up getting Romney to talk unapologetically about his success or even to explain to voters why he struggles to connect.

“I think he genuinely is a modest person. That explains some awkwardness or apparent unease in dealing with it,” said Mark DeMoss, a senior adviser and prominent evangelical leader within the GOP.

“It’s difficult for him to understand why people would think of him not understanding their daily travails because of his enormous wealth,” said Douglas Gross, who chaired Romney’s 2008 campaign in Iowa but is not involved with his campaign now. Romney perceives that he’s “lived his own life in a way that’s not extravagant, [and so] he doesn’t understand why people wouldn’t think he understands their pain.”

Gross recalls confronting Romney directly on this gulf in their first meeting. “I asked him, ‘You’re an incredibly successful guy and can you relate to average folks in the cafes of Iowa?’ and he found that question insulting and refused to answer it. To me, that’s the microcosm of the problem.”

At most rallies these days, Romney’s appearance is preceded by a biographical video that depicts him as warm, frugal and a bit silly. And, Tagg Romney said, the campaign plans to air ads soon in which other people talk about the Mitt Romney they know.

It is not in his father’s temperament to “talk about how he cares about other people and cares for people,” Tagg Romney said. “He’s not going to change.”

This week, Mitt Romney tried once again to relate. “My heart aches for the people I’ve seen,” he told people at a rally in Westerville, Ohio, on Wednesday.

Later that day, asked in an NBC interview how he can “better connect with Americans,” Romney offered an accomplishment, rather than a declaration of his feelings — the universal health-care law that he signed as governor of Massachusetts.

“One hundred percent of the kids in our state had health insurance,” he said of the law that was the model for Obama’s Affordable Care Act — which Romney has vowed to repeal.

“I don’t think there’s anything that shows more empathy and care about the people of this country than that kind of record.”

Shaped by family history

One of Romney’s sons, Josh, suggests that his father’s philosophy about his fortune is rooted in family history, a narrative of personal perseverance and persecution that also is the group history of the Mormons.

“It all stems from his father, who was born in 1907 in Mexico and lived in very poor circumstances, and had to flee Mexico, and was on government relief for a short time, and lived in Salt Lake through the Great Depression,” says Josh. “I think that experience for him and his family’s reaction . . . to that kind of circumstance really kind of shaped our family and my dad.”

What did it teach? “How to value money, how to value the dollar.”

Romney duct-tapes the holes in his gloves, duct-tapes the gap in his campaign bus ventilation system. He rinses and stacks the dishes at the sink before loading the dishwasher after family holiday meals. He picks up his own dry cleaning, pulls his own suitcase, eats at burger joints, counts his change.

While other rich people flaunt their acquisitions, the Romneys tend to flaunt their frugality. When another one of his sons fetched free wood pallets advertised on Craigslist, broke them down and used the discarded rough planks to repanel his “man cave,” his wife proudly chronicled the do-it-yourself project with photos and text on her blog.

“He’s probably the most frugal person I’ve ever met,” another Romney daughter-in-law, Laurie, said at a Women for Romney event in Lone Tree, Colo., 10 days ago. She joked that if you turned your back on a running faucet for a second, Mitt Romney would shut it off, that he consolidated the garbage “because the waste management company in his area charges by the bag.”

On the other side of this ledger are vast expenditures for family comfort.

His five sons are beneficiaries of a family trust valued at more than $100 million — as long as they keep working. “He’s said if you guys ever decide to stop working,” said Josh Romney, “you can guarantee you’ll never see another penny from the family.”

He’s spent millions updating and expanding the compound on Lake Winnipesaukee in New Hampshire into a family playground of horses and barns, powerboats and water toys. He’s seeking to triple the size of the couple’s $12 million San Diego beachfront home and include an underground garage with an elevator lift. He supports his wife’s passion for the expensive equestrian sport of dressage.

He has permitted himself one other great luxury: running for public office.

Romney has spent about $53 million of his own money on his campaigns, starting with his first bid, in 1994, to unseat Ted Kennedy as a Massachusetts senator. He spent $6 million to run for governor, $45 million on his 2008 presidential campaign and $150,000 this time around. It was money he earned as the co-founder and CEO of Bain Capital, a venture-capital firm that became spectacularly successful in creating wealth for investors.

His success with money, and his habits with it, have both expanded his world and narrowed his vision of how everybody else lives.

While he went to an elite private school and then Stanford and Harvard, and borrowed $42,000 from his father to buy his first house, in Belmont, Mass., he often describes himself as having “inherited nothing” because he and his wife gave away the money they received from their parents’ estates.

“Within Mormon culture, there is a strong egalitarian impulse,” said David Campbell, a political science professor at Notre Dame University and a Mormon who specializes in religion and politics. “There’s no paid clergy, so you might very well have someone who is a schoolteacher as the bishop and within the flock investment bankers and neurosurgeons, but he’s the pastor and in charge. Beyond that, there’s this ethos of people being not just frugal, but also using foresight in their planning.”

Within such an ethos, it might seem ordinary to suggest that a high school graduate should just borrow money from his parents to get on with life, as Romney did this spring during a campaign stop at Otterbein University in Ohio. “We’ve always encouraged young people: Take a shot, go for it, take a risk, get the education, borrow money if you have to from your parents, start a business,” Romney said.

The derision that greeted those remarks followed Romney all the way to Charlotte in September. There, delivering the keynote address at the Democratic National Convention, Julian Castro, the 37-year-old mayor of San Antonio, paid tribute to his single mother and the grandmother who arrived in Texas as a 6-year-old orphan, then repeated Romney’s words. “Gee,” said Castro, “why didn’t I think of that?”

The ‘cheapskate’

‘Mitt is a cheapskate,” says Fraser Bullock, lifelong friend, fellow Bain partner and fellow Mormon. “He watches every penny. This is in his DNA.”

When Romney goes to the movies, he pops a bag of his own popcorn at home, stuffs it into his wife’s purse and sneaks it into the movie theater so he doesn’t have to buy a snack he considers overpriced.

The candidate has thoroughly incorporated the modern instantaneous connectivity of his iPad into his now-frenetic life, but he downloads only free applications, friends say. He is so rigid about this that he continued to revise his speeches through a cumbersome process of text changes in e-mails, complaining all the while — but refusing to buy Apple’s Pages word-processing program because it costs $9.99. Finally, a senior staffer told an aide to buy it and download it onto Romney’s iPad when he wasn’t around.

Some might applaud Romney’s insistence on freeware as a harbinger of a president who would rein in spending and cut waste.

Others might question if that’s the best use of his high-priced time — and why he would not want to spend money on the entrepreneurs and creative minds who developed the product.

“He respects money very much, he is conscious of it, he wants to get maximum value out of it,” says Cindy Gillespie, whom Romney hired as the D.C.-based lobbyist for the Salt Lake City Winter Games. “But at the same time, he is not in any way personally cheap.”

He gave her a tight budget for office space, “and I went thrifting and I found a great spot on Connecticut Avenue between Burrito Brothers and Bubbles Hair Salon in a third-floor walk-up,” she says, which she furnished with beat-up discards from the General Services Administration. “The place was awful, but he loved it.”

Earlier in the campaign, before he received Secret Service protection this year and began using a chartered plane on the campaign, Romney flew coach and even refused to pay the $10 to Southwest Airlines to earn early boarding. But he had no objections to letting one of his top strategists buy a better boarding position — and expense it.

He has a taste for both fine French restaurants and neighborhood ethnic joints, and he tips well at both, say those who have served him and dined with him.

But he carries his own bags — no tip for the bellman there — and washes his dress shirts in the hotel room sink at night and irons them in the morning.

Josh Romney remembers his parents getting an estimate to repair a sunken brick walkway between the garage and the house shortly after the family moved, in 1989, to their seven-bedroom Belmont home. Romney was a newly rich man; Bain Capital had completed its first two takeovers, making its partners millionaires nearly overnight.

“I remember my mom and dad being flabbergasted at the price. They just couldn’t believe it. They just said that’s way too expensive,” says Josh, who was 15. “So my dad enlisted me and said, Josh, we can do this way cheaper than that. We went and got the brick and sand and dug the area out and we spent every Saturday for the next few months building that brick walkway and actually did a pretty remarkable job. It’s still standing today and doing quite well. . . . Here’s a guy that at that time was making a pretty good living in the business world and easily could have paid for it, but just couldn’t bring himself to waste that kind of money.”

Says a political adviser who spoke on the condition of anonymity to talk frankly about Romney’s habits: “I watched him go into an outdoor cafe in Santa Monica once and a guy at the table ordered a Perrier off the menu and Romney looked at the price and said, no, no don’t do that, walked across the street to the 7-Eleven and bought a six-pack of Perrier and said, let’s just drink this. He is frugal to the extreme. It’s a joke within the campaign. It kills everybody that’s been around him.”

The emphasis he places on doing it cheaper himself could frustrate those doing business with him, however.

Geoffrey S. Rehnert, one of Romney’s original partners at Bain, cites the hiring meeting for a new chief executive for Calumet Coach, a medical equipment company that was one of Bain’s first acquisitions in 1986. When the recruiter put the salary demands for the top candidate on the table, Rehnert says he thought “Mitt was ready to throw up.”

In hindsight, the candidate’s request was within the industry standards at the time — and Bain would go to reap $34 million on its initial $1 million investment — “but Mitt was just so pained” to pay the sum, Rehnert says. “The executive-search guy looked at him and said, ‘Mitt, you throw nickels around like they’re manhole covers.’ ”

Religious refugees

The story of the Romney family is both more wretched and more resilient than many people know.

For most of their five generations in this country, the Romneys were both the seekers and the hunted, often at the same time.

They became ardent leaders of an upstart religion that led them in ox-drawn wagons through a wild West to a valley by a lake of salt. At each place they alighted, the Mormons bent their shoulders to the wheel and prospered, thus provoking the envy, suspicion and hatred of their countrymen.

Several times, the Romneys were chased from their settlements by mobs with fiery torches and the slightly more civilized uniforms of the federal government, which periodically throughout the mid-1800s outlawed their religion for practicing polygamy.

George Romney, Mitt’s father, was born into prosperity on a thriving ranch his grandfather coaxed from dirt in Mexico, where he had fled with his three wives after a mob came to kill him at the Mormon settlement he had founded in Arizona.

When the Mexican revolution broke out, the Romneys fled back to the United States, penniless. George Romney was 5 at the time, and he remained bitter all his life about the exile, describing his family as among “the first displaced persons of the 20th century.”

Like his forebears, George’s father would go “broke five times,” as Mitt Romney’s older brother, Scott, describes it. George Romney himself sold paint out of the back of his car, his son has taken to saying on the stump, to keep his own young family afloat.

Mitt Romney always seems to have kept score with dollar signs.

Asked to declare which baseball team he followed earlier this year during an interview with Michigan’s Grand Rapids Press, Romney said this:

“Oh, Red Sox, I’m afraid. I grew up a Tigers fan, of course, and Al Kaline was my hero. I remember one game, we were at Tigers Stadium . . . and the guy in the next box was cheering ‘Mickey Mantle, Mickey Mantle, he’s our million-dollar player, he’s our million-dollar player.’ We were playing the Yankees, of course. And then Roger Maris came up and ‘Roger Maris, he’s our million-dollar player.’ Then when Al Kaline came up I said, ‘Al Kaline, he’s our five-million-dollar player.’ Of course, today that would seem like small money, but not back then. But I was about 10, and I was very irritated with the Yankees.”

This is an unusual anecdote for a presidential candidate to offer up about himself 55 years later. And it’s inflated: Nobody made millions in baseball in the late 1950s. It seems to illustrate that even as a child, Romney used money to calibrate value.

He didn’t manage to defeat Ted Kennedy in their Senate race, but for years he has bragged that he got close enough to force Kennedy to “take out a second mortgage” to pour money into his campaign.

The repeated inability to keep himself from sounding superior comes from “a grinding obsessive quality to make himself appear to be more perfect than he needs to be and more perfect than he is,” suggests Ronald Scott, a former Time reporter who is a distant cousin of Romney’s and has known him for years through church. At the same time, Romney refuses to acknowledge that his money and his almost prim attitude toward it create a distance with voters.

And while he was born long after his father’s paint-selling days, Romney made it clear at that fundraiser caught on tape in Boca Raton, Fla., that he actually sees himself as self-made as his father, saying that even though his and his wife’s fathers “did quite well,” when they “passed along inheritances to Ann and to me, we both decided to give it all away. So, I had inherited nothing. Everything that Ann and I have, we earned the old-fashioned way, and that’s by hard work.”

The crowd applauded. He added: “I say that because there’s the percent that’s, ‘Oh, you were born with a silver spoon.’ You know, ‘You never had to earn anything,’ and so forth. And, and frankly, I was born with a silver spoon, which is the greatest gift you could have, which is to get born in America.”

Scott Clement and Jason Horowitz contributed to this report.