WILLIAMSTOWN, Mass. — The first thing David Weathers thought when his parents dropped him off at Williams College freshman orientation was, “Damn, I’m really on my own now.” People didn’t understand the slang of his working-class Chicago suburb. Lots of students came from “big, powerhouse private schools.” Many of his football teammates didn’t think $400 cleats were expensive.

But as the weeks went on, he fell in love with the school. He formed a brotherhood with his teammates and bonded with other freshmen in his dorm. Everywhere he turned, administrators were checking in with him, asking if he had questions, pointing him toward seemingly endless resources.

“This place treats their students right,” he said.

Yet a month into the school year, Weathers faces a problem big enough to distract him from studying and give his father an ulcer: An outstanding bill of $42,300.

Weathers, who graduated at the top of his class at a charter school on Chicago’s South Side, is the first in his family to attend a four-year college—a beacon of upward mobility for people with deep roots in the working class. But unlike many first-generation students, his family has made a comfortable income in the last few years. In 2013, after a career spent clawing his way up through the music industry, Weathers’ father made $175,000 as a regional production director for Live Nation Entertainment. Despite a six-figure income, the family of six isn’t exactly rich. After expenses, there’s not enough left to build a college fund that could cover four years of an elite education, and there’s no wealthy relative picking up the slack.

But according to Weathers’ award letter from Williams, $175,000 a year means his family should contribute nearly a third of its post-tax income to their son's education.

In the last few years, more colleges and universities have pledged to tackle the problem of “undermatching”—recruiting high-achieving, low-income kids to apply to the Ivy Leagues and other elite institutions who have enough endowment to provide free rides to needy students. Some schools, including Williams, have been putting their money where their mouths are; 18 percent of Williams students now pay no tuition at all. To offset the cost, these schools often aggressively recruit students whose families can pay the full cost of attending—more than $60,000 a year at most top private colleges.

That often leaves students like Weathers forced to choose between taking out a huge number of loans and nearly bankrupting their families.

At expensive, elite institutions whose financial aid is need-based, not merit-based, “you basically don’t have the middle class anymore,” said Elizabeth Armstrong, co-author of Paying for the Party: How College Maintains Inequality. Three-quarters of the students are in the top quartile of income, “and then there are poor students, and almost none in between.”

“The vast majority of Americans are nowhere close to being able to manage this situation comfortably.”

"Middle class" can encompass a range of incomes; the median income in the United States is around $60,000. Jim Kolesar, Williams' vice-president of public affairs, says current students from families with incomes between $60,000 and $68,000 are paying an average of about $6,000 per year. Although he wouldn’t comment on Weathers’ specific situation, he asserted a case like this was “highly unusual.” Indeed, Williams has the fifth highest endowment of any liberal arts school in the country, and the average amount of debt for a Williams graduate is only $12,474. Williams does better than most in terms of recruiting and providing for low-income students.

Still, Weathers’ quandary shines a spotlight on just how expensive an elite college education is, even for a striving, upper middle-class family—and whether it’s worth it. Weathers may have been able to graduate debt-free from the University of Illinois, which regularly awards merit scholarships. But shouldn’t a black, male valedictorian from the south side of Chicago go to America’s number-one ranked liberal arts school if he has the chance?

David Weathers (left), a 17-year-old freshman at Williams College in Williamstown, Mass., laughs with a football teammate on the way to practice. Yana Paskova / for NBC News

On paper, a $175,000 annual income seems like a lot. But Chris Weathers, David’s father and the sole earner in his family, insists he lives paycheck to paycheck.

“I have a modest house,” he said. “Two cars. Four children, a wife, two grandchildren. Two of my [adult] daughters have struggled to find decent-paying jobs…so I help them out. I’m not running up any credit cards.”

Chris Weathers’ six-figure salary is relatively new, and as soon as he started doing well in the music industry, he needed to erase a decade’s worth of debt instead of start a college fund. “My parents are working-class,” he said. “We don’t have that family money.”

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In other words, there’s a difference between income and wealth. Making a decent salary doesn’t guarantee that a family will be able to pay for college. And in a difficult economy, the numbers on a student’s Free Application for Federal Student Aid may not tell the whole story.

“The FAFSA formulas just don’t work out very well,” Armstrong said. It doesn’t take into account a household’s expenses, geographic location, or obligations to non-minor children. “The vast majority of Americans are nowhere close to being able to manage this situation comfortably.”

“My whole preconceived notion about college was that if you do good in school, you get scholarships.”

David is the youngest of four Weathers children. The family had high hopes for him when he started at Johnson College Prep, a charter high school in a low-income area. The school emphasized higher education and walked him through the college application process. Around the same time, a counselor from the Chicago chapter of Kappa League, a national organization that provides mentorship to black, male youth, took Weathers under his wing, too. Over the next four years, he got excellent grades, joined mock trial and the football team, and got a 32 on his ACT.

When senior year rolled around, Weathers didn’t even apply to safety schools.

“My whole preconceived notion about college was that if you do good in school, you get scholarships,” he said.

In April, he got into Pomona College, Notre Dame, Northwestern, Grinnell College, University of Washington in St. Louis, University of Southern California, and Williams College—all prestigious institutions. Notre Dame was hinting at a generous financial aid package, but the clear choice, rank-wise, was Williams. His advisor from Kappa League said he’d get much more personal attention there than at a big university. So without worrying about the money, Weathers resolved to enroll at Williams—even after his family received their award letter from the school on April 30, 2014. They learned that although Williams had given Weathers $15,320 in grants, his “estimated family contribution” would be $42,300, far more than Chris Weathers says he can afford.

“If I were to pay that amount of money today, I would be flat broke,” he said.

Christine Tamir and David Weathers, a 17-year-old freshman at Williams College in Williamstown, MA, chat in their dorm . Yana Paskova / for NBC News

At that point in the admissions process, a legacy of attending college or being surrounded by college-educated people may have helped Weathers’ family. Savvy parents often pit one elite school against another, trying to negotiate a better financial aid package. Or the family could have applied to the University of Illinois’ smaller honors college for standout students.

The family didn’t know any of that. Navigating the financial aspect of college, which Chris Weathers called “a never-ending loop,” can be a mind-boggling process, even for highly-educated parents. Armstrong mentioned that even though she’d written a book about college, knew many admissions officers, and grew up with a professor as a father, she was “baffled and befuddled by the money and the logistics" for her own child. "It’s almost impossible to navigate well.”

Still, Weathers reassured his family, who didn’t know much about applying for loans, that it would all work out. April turned into summer, which dragged into fall, and on the first day of school, Weathers still hadn’t gotten the loans he needed. He said he applied to scholarships, but they were all need-based. So now, weeks after school has started, he’s scrambling to get a loan, while his father has applied to refinance his home. The first time Weathers went to the financial aid office to see if he could improve his package, he said a school official suggested he look into transfer options.

“That was really discouraging,” he said. “I was like, ‘I got accepted here for a reason. I’m not leaving’…I didn’t think I’d go broke trying to go to school.”

First-generation students can do well in state schools, but their upward mobility “may be far slower.”

But some would say the financial aid officer had a point. If, hypothetically, his financial package stays the same for four years, Weathers will be staring down nearly $170,000 in debt. Michael Fabricant, a Hunter College professor and author of Organizing for Educational Justice, says going to a public university allows a middle-class student “to sidestep all that debt. There’s a real power in being able to build a life right out of college without worrying about student loans.” Debt requires a graduate to immediately seek out a few high-paying industries, like finance, rather than “engage in experimentation he or she would otherwise be able to.”

A well-known Brookings Institution study by Stacy Dale and Alan Kreuger found that for the majority of students, the most important factor in long-term success is whether one earns a Bachelor’s degree, not where it’s earned. But the study made an exception for low-income and first-generation college students. In those cases, the networks and personal attention the students have access to in elite colleges make all the difference. At a big, impersonal university, said Fabricant, “you don’t forge relationships with people whose families are affluent and have vast networks.” First-generation students can do well in state schools, but their upward mobility “may be far slower.” These students are 13 percent more likely to graduate in six years from a private institution than a public one.

“If you want to join the leadership class in American society, you’re better off staying at a place like Williams,” said Richard Kahlenberg, senior fellow at the Century Foundation. “Look at where our Supreme Court justices have gone. Look at our last few presidents.”

Weathers loves Williams because of the “super-intelligent people” surrounding him. He wants to be a lawyer or a neurologist, although he has the disposition for politics—he can’t walk 10 feet on campus without running into someone he knows. Everyone seems to want to be friends with him. On a typical afternoon in his dorm, his hall mates will knock on his door to come hang in his unusually spacious corner room, outfitted with a lava lamp and hang-a-round chair.

Weathers said he’s already struck up a rapport with the professors who teach his classes, two of which have fewer than 30 students. And before classes started, Weathers benefited from a pre-orientation program devoted to first-generation college students, meant to soften the blow of culture shock.

“It’s an invisible identity,” said Rosanna Reyes, an associate dean at Williams and a first-generation student herself. “It’s easier to get lost…bigger schools don’t have the ability to devote so much energy to helping these students.”

David Weathers, a 17-year-old freshman at Williams College in Williamstown, Mass., meets with his academic advisor. Yana Paskova / for NBC News

Programs like Williams’ pre-orientation are becoming more common, and to their credit, many institutions, regardless of endowment, are making sure they set aside funds for low-income students. But where does that leave families like the Weatherses?

“The middle class gets squeezed,” said Kahlenberg. Lots of colleges have yet to recognize that “not just the poorest are in need.”

But the deeper issue, said Fabricant, is the nation’s unwillingness to invest in public education. “The government has completely eviscerated funding that would allow a middle class or low-income student to cushion himself from debt,” he said. Fifty or 60 years ago, a kid like Weathers could have gone to a state university for free. Now, he’s taking a huge risk on his financial future that almost amounts to an “individual speculative bubble.”

Chris Weathers remembers balking at the price of University of Illinois—up to $35,000 for in-state tuition, room, and board. But now he regrets overlooking that option.

“In hindsight, I should have told David [that Williams was] just not gonna happen,” he said. “Because of the high emotion, there wasn’t enough logistical reasoning being done.”

As for David, the daunting price tag doesn’t seem to faze him. He’s focused on completing a world-class education at all costs.

“If I just work hard and do my part now,” he said, “ultimately I think I will come out on top.”

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