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Nearly 80 years ago, around the time a Kansas-born carmaker was putting his name on the newest, tallest, shiniest building in the world, a young auto mechanic named Morris Weinberg opened a repair shop on busy Brooklyn Avenue in Kansas City, Mo. As he modestly prospered, fixing and selling used cars, Weinberg dreamed that his son would enter the auto business. Not used cars, though — new cars. Sleek and powerful cars, like the ones built by Walter Chrysler's company. And that's how Steve Weinberg, with his father's savings to stake him, came to open a Dodge dealership in Grandview, Mo., in 1966.

On May 14, 2009, a panel truck pulled up to Weinberg Dodge bearing a letter from Chrysler, informing Morris Weinberg's son that his career in the new-car business would be over in about three weeks. There wasn't much in the way of explanation, but it comes down to this: Chrysler's sales can't support a dealer network built for another era. (See the 10 milestones on the way to GM's bankruptcy.)

Neither can General Motors'. The company is in the process of axing 1,100 of its 6,000 dealers. When the march of time, the sins of management and the scythe of a bad economy conspire to bankrupt once great companies, who pays? The sort of person, in the words of Tennessee Senator Bob Corker, "who ran a profitable business, civic leader, always responsible," who "very unfortunately" is "going to take a lot of pain" for the mistakes of others. A guy like Steve Weinberg. "It breaks your heart," says the Senator. (See the 50 worst cars of all time.)

Better to break hearts locally than shatter the greater economy — and that's what the collapse of GM and Chrysler threatens to do, according to the White House auto task force that is undertaking the monumental rescue mission. In the deal being cobbled, GM's stockholders will be wiped out, replaced as equity owners by the Treasury Department, with 70%, and the United Auto Workers (UAW), with 17.5%. GM's business in Europe, Opel, will be sold. As many as 14 U.S. factories are marked to close. The iconic Pontiac brand is probably finished. Under a new labor agreement with the UAW, GM's hourly domestic workforce, which numbered 600,000 at its peak, will drop to 40,000. In other words, 14 of every 15 GM jobs have vanished in roughly a generation. And the ripples: dealers losing franchises, thousands of suppliers doomed.

And that's if things go according to plan. Holders of $27 billion in GM bonds have refused the company's debt-for-equity swap, making bankruptcy all but inevitable. For purist capitalists, the lasting significance of GM's pending Chapter 11 (and Chrysler's bankruptcy, filed a month ago) is the overwhelming intrusion into the private sector by Barack Obama and his auto task force at Treasury. "The day they fired the CEO of General Motors" — Rick Wagoner was dismissed by task-force co-chairman Steve Rattner in late March — "is a day we will look back on with great regret," predicts Corker, a reluctant and critical supporter of the bailout. "The government has no business making those kinds of decisions." Critics of the government's involvement maintain that bondholders have been punished, union workers coddled and laws flouted in the process. And they worry that should GM emerge from Chapter 11 with the U.S. Treasury as majority shareholder — Government Motors — we will have crossed a frontier separating capitalism from socialism, even though the company will be run by existing management.

The Obama Administration is unswayed, pointing out that the Bush Administration had intervened with government loans by the time the new team arrived. Chrysler was a dead man walking, and GM was a problem that no bank or investor group would touch. Task-force officials believe that the only alternative to a government cleanup, financed with public money and rammed through by government muscle, was the chaos of liquidation, which would have triggered a cascade of business failures and rocketed the unemployment rate above 10%. (Watch an interview with Ford CEO Alan Mulally.)

Who else but the government would pay the suppliers, fund the sales incentives, guarantee the warranties that would keep local economies limping along from Fresno to the Finger Lakes? "These companies were saddled with an impossible set of liabilities," a task-force member explained. "Our job was to clear up their balance sheets, restructure their debt, cut their costs and put the new management in a position to execute a turnaround. And we hope that a part of that will be an increased focus on designing and building products that people want to buy."

Which brings up another sore point among skeptics of the Administration's actions. Is it feasible now for GM and Chrysler, which made money on pickups, SUVs and minivans, to small-car their way to prosperity? U.S. carmakers have not earned a dime selling automobiles in a decade. "There's no question it's a challenge," a task-force official allowed. "It's something the domestic car companies haven't done successfully in the past." Whether it will work in the future is "a fundamentally significant question."

In other words, for all the number-crunching and all the brute financial haircuts involved in these bankruptcies, at heart they are animated by the audacity of hope. The hope that Fiat's Sergio Marchionne can translate his turnaround mojo into a language Chrysler can understand. The hope that, having poured at least $1 billion into the innovative but commercially suspect Chevy Volt plug-in, GM can pivot into less costly hybrid and high-efficiency diesel technologies. (Perversely, the Administration might hope for $4-a-gallon gasoline to aid that quest.)

And these hopes float on the audacity of deficit spending. By the time taxpayers are done cleaning up the books of the two companies and refilling their tanks with enough cash to keep them going — along with their finance arm, GMAC, and their key suppliers — the public price tag will exceed $100 billion. Add billions more in subsidies for researching and developing green technology and still more billions in tax credits to motivate buyers to go green. If someday GM and Chrysler become consistently profitable, the government loans will be repaid and both companies restored to total private control. The operative word being if.

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Kicking the Can
When Obama drafted Rattner and another financier, Ron Bloom, to lead his auto task force, he instructed them to "treat these transactions in a commercial manner." That is to say, restructure the companies in a way that makes good business sense. The "commercial" mantra proved fleeting. The first imperative of commerce — to add value and thus earn profits — is too narrow to host all the civic expectations attached to the auto industry. If GM's only task were to make money, the company would shutter its car factories (or move them to low-cost countries) and churn out light trucks.

But that's not possible at a time when Obama and congressional leaders are requiring Detroit to do more to advance conservation and alternative energy and create 5 million green jobs. "I am absolutely committed to working with Congress and the auto companies to meet one goal: the United States of America will lead the world in building the next generation of clean cars," Obama said in March. Other public buttons have been pressed as well. Senators Robert Byrd and Jay Rockefeller of West Virginia called on Treasury to go easy on small-town car dealers, who create jobs and pay taxes in far-flung communities. Pension and health-insurance benefits that might have been wiped out in a strictly commercial bankruptcy have instead been elevated to priorities. (See pictures of GM factory-scapes.)

On March 26, Obama convened the task force in the Roosevelt Room. By then, as Rattner explained to the President, a commercially sound plan for a stand-alone Chrysler was out of the question; it was deeply in debt, bleeding money and saddled with unpopular products. Of the 20 best-selling vehicles in the U.S. in 2008, only one, the Dodge Ram pickup, was made by Chrysler — compared with five for GM and four for Ford. A venerable European carmaker, Daimler, had already tried and failed to revive Chrysler. Its current owner, the private-equity fund Cerberus, had spent months of fruitless globetrotting in search of another car company willing to give it a try.

Make that nearly fruitless. Marchionne, CEO of Italy's Fiat, had sniffed an opportunity lurking by the Chrysler deathbed. Chased from the American market a generation ago by its comic reputation for poor quality, Fiat seemed an unlikely rescuer. But Marchionne entered the picture as the It boy of the auto world, having slashed costs, retooled management and refreshed styling to boost sales of the firm's cute little cars. He wanted back into the U.S., provided it didn't cost him anything. (Watch TIME's video about an optimistic Dodge dealer.)

His lowball — bid seems the wrong word — offer went like this: If the U.S. government would wipe out Chrysler's shareholders, buy out its bondholders, cut wages and jobs, deal with its retirement liabilities and fund the warranties, then Fiat would take a crack at Chrysler. The Italians would bring their cars to Chrysler's showrooms and share their advanced diesel technology with Chrysler engineers. Chrysler might sell some cars in Fiat's markets — Jeeps may have the best overseas appeal. Marchionne would lend his managerial chops. And if things worked out, Fiat would take a controlling share.

Rattner, an icy-eyed, sharp-spoken Wall Street dealmaker, laid out Obama's unappealing options. Chrysler could be scrapped for parts through an unstructured bankruptcy. Or the task force could try to make the Fiat proposal work, using the leverage of bankruptcy to force concessions and the Treasury's wallet to refinance the debt and recapitalize operations as debtor in possession. Some task-force members argued that, painful as it would be, liquidating Chrysler would strengthen the survivors — GM and Ford.

Bloom argued Fiat's case, Chrysler's case and ultimately the UAW's case. Gangly and soft-spoken, Rattner's co-chairman is passionately pro-union — an unusual trait among investment bankers. He helped guide the steelworkers' union through the collapse and restructuring of its industry, and this time he came to the aid of Chrysler's workforce. Gene Sperling, a veteran of the Clinton Administration, added his weight to Bloom's, speaking movingly of the human devastation that would follow should Chrysler collapse at such a weak moment for the overall economy.

Obama asked Rattner to rate the chance that a Fiat deal could be struck, given all the competing interests and Chrysler's extremity. "Fifty-one percent," Rattner answered. "And in my experience, deals get worse, they don't get better" as they take concrete form. On that note, Obama decided to press ahead, sparing Chrysler from the merciless marketplace.

Over the next month, the task force rammed through an odd-looking arrangement: The government would put up the money. The UAW's Voluntary Employee Beneficiary Association (VEBA) — a trust set up at Chrysler and other U.S. carmakers to shift retiree health-care obligations off company books — would own a majority of the shares. Fiat would run the place. And some sort of entity called Chrysler would survive. Despite the protests of some bondholders, the deal was sent to receive the blessing of a bankruptcy judge.

Was it commercial? Experts scratched their heads. "We're all kind of struggling with it," says automotive consultant Laurie Harbour-Felax. To Corker, the deal was an exercise in pain management. "I get the sense that they decided to kick the can down the road, maybe delay the end for another four or five years," he says. "And then if it fails, at least a foreign company owns it."

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The Politics of Haircuts
GM followed Chrysler toward bankruptcy like the next car on a roller coaster. The path was clear: if Chapter 11 was necessary to restructure the smaller, privately owned company, it would surely be needed to resolve the troubles of the publicly held behemoth. But simply seeing where things were headed didn't change the fact that it would be a wild ride.

The failure of GM was a long time in coming, but in a sense, its case was more promising than Chrysler's. Given the strides GM has been making to repair decades of mismanagement — streamlining production, coordinating design, improving quality — there was a chance the company might have saved itself in a better economy. But with American vehicle sales dropping from 16 million in 2007 to a projected 9 million or 10 million this year, GM had no hope of servicing its massive debt. (See the 12 most important cars of all time.)

The company put Saab, Opel, Saturn and Hummer up for sale, then killed Pontiac. (Marchionne promptly entered fire-sale bids for Opel and Saab.) As the expected bankruptcy filing approached, plans were under way for a complicated stock deal that would render existing shares essentially worthless. Secured bondholders were being offered full payment in new company stock, while others were being told to expect far less.

The UAW, meanwhile, has been asked to take a deal similar to the one struck with Chrysler. Autoworkers would give up some holidays and bonuses. Their wages would not automatically rise in the future as they had in the past. Some 20,000 jobs would be cut, and future hires would earn wages comparable to those paid in Toyota's U.S. factories. When those givebacks are added to an earlier surrender of the notorious "jobs bank" — which paid laid-off autoworkers for doing nothing — clearly the UAW's once heavenly bed has lost much of its fluff. What remains is the VEBA, the multibillion-dollar trust fund designed to protect a key element of the membership's fabled retirement benefits — which the union refers to as deferred wages. As in the Chrysler deal, the UAW agreed to trade a chunk of the cash GM owed the VEBA for 17.5% equity in the company and other considerations. (Read about Detroit's efforts to reinvent itself.)

This piece of the transaction has proved most controversial — and is perhaps the biggest potential obstacle to a smooth reorganization of GM. The problem: the VEBA's haircut — trading promised cash for riskier shares — is less severe than the deal offered to some bondholders. And that's not the way bankruptcy is normally done.

Bankruptcy law ranks claims against a failed company. Stockholders have the weakest claim — they made a bet on success, got failure instead, so too bad. The strongest claims belong to secured lenders, which are first in line for any proceeds if the company is liquidated. In between lie the unsecured claims. For a carmaker, this creditor class includes suppliers who haven't been paid, car owners whose repairs ought to be covered by warranty, dealers seeking reimbursement for manufacturers' rebates — and the UAW seeking a VEBA payment.

Some lenders have been galled to see the Democratic Administration, whose party receives millions from the UAW each election cycle, giving a sweeter deal to the union than was offered them. Task-force members counter that other unsecured claims have received even better deals than the union's. Warranties, for example, have been 100% guaranteed — no haircut at all. "We're trying to avoid liquidation, and so these claims have to be classified according to their importance to the future viability of the company," a task-force official explained. "Obviously you can't sell cars without warranties. You can't make cars without suppliers. So most of those claims are being paid. And you can't build cars without skilled workers."

A few Chrysler bondholders tried to resist but were overwhelmed by the megabanks that held most of the secured debt. Having taken billions in bank bailout money, they were in no position to irritate the Treasury Department. GM's debt is more widely dispersed, however, which makes it harder to muscle a settlement. To avoid a morass in court, the task force agreed at the 11th hour to fully repay GM's secured lenders, using stock in the reorganized company.

See the best cars from the 2009 Detroit Auto Show.

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A Death in the Family
So the bottom line: the government's auto rescue is perhaps misshapen, certainly improvised, highly controversial and hugely expensive — up to $70 billion and counting for GM alone. In Chrysler's case, success is a long shot. As for GM, the restructured company will find itself struggling to balance the many demands our society places on the auto industry.

Surely a lovely outcome was never in the cards. "We're dealing with something unprecedented — these huge companies, a historic recession. There was no rule book," a government official argues. To some questions there are no perfect answers. (See the 50 worst cars of all time.)

That said, the story of the car companies is characteristic of the government's policies throughout the economic crisis. Treasury elbowed aggressively into the boardrooms and executive suites, much as it has done with the banks. When possible, Uncle Sam's thumb has pressed the scale in favor of the people the government sees as underdogs — the autoworkers, homeowners facing foreclosure. The ordinary folks in between — the dealers, some partsmakers — are on their own.

In an office crammed with photos documenting his family's history, Steve Weinberg, 66, reread the letter from Chrysler for the umpteenth time. "It's just so cold," he said when he looked up. "I mean, it's brutal." At a time when people aren't buying cars, he had $1.5 million of new inventory on his lot — inventory the company bosses had begged and cajoled him to purchase as they struggled to stay afloat. "I thought I was being loyal. I can't move that in three weeks!"

You figure car dealers must be a resilient breed, but this has flattened Weinberg like a Ram squashing a soda can. "I don't sleep," he said. "It's like — well, it's like a death, a death in the family." A family with 32 employees.

I told this story to a government official with intimate knowledge of the Obama auto task force, who spoke, as they always seem to do, on background. "The mom-and-pop days are kind of over," the official replied — with a little shrug that somehow epitomized the uneven impact of this slow-moving tragedy.

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• David Von Drehle
• You wouldn't assemble a car the way the White House auto team cobbled together deals to keep Chrysler and GM going. So why are taxpayers about to foot a $100 billion bill for a vehicle that might not run?