This week, what many skeptics have come to consider the unthinkable happened: A Wall Street banker faced certain legal consequences for unscrupulous trading practices.

On Tuesday, former Goldman Sachs banker Rohit Bansa agreed to plead guilty to charges of taking confidential documents from a source at the Federal Reserve Bank of New York, where he worked as a regulator for several years prior to his stint with the investment giant. Along with his source, a former New York Fed worker, Mr. Bansa could face up to a year in prison and a permanent ban from the banking industry for using the leaked documents to gain an unfair advantage when facing clients. Goldman Sachs, meanwhile, could face up to $50 million in related fines.

Bansa’s case is remarkable, in part, because criminal prosecutions are still rare on Wall Street. But it comes as the federal government has put a new emphasis on holding individual executives accountable for their companies' actions, and as white-collar workers and executives in other corners of the corporate world are even now being held accountable for corporate wrongdoing.

The trial of former Massey Energy CEO Don Blankenship marks “the first time in 150 years of Appalachian mining that the top boss of a coal firm has ever had to answer for how he ran his company,” according to Slate. That trial is set to conclude in November. And last month, the former CEO of the Peanut Corporation of America was sentenced to 28 years in prison for his role in a deadly salmonella outbreak in peanut butter – the largest ever in a food safety case in the US.

Meanwhile, a United States Department of Justice investigation into FIFA, world soccer’s governing body, is focused mainly on high-ranking officials and top aides to former president Sepp Blatter (and possibly Blatter himself) on multiple charges of corruption.

Those cases, along with upcoming legal action surrounding Volkswagen admitting falsifying emissions tests on millions of its diesel fueled vehicles, will serve as a test of the recent Justice Department mandate. For organizations like VW, Goldman Sachs, and FIFA, that could mean the end of a legal landscape, in the US at least, where cases can be settled with a few multibillion dollar checks.

Far cry from Teddy Roosevelt

In the years since the 2008 credit collapse, when not a single banking executive went to jail for unscrupulous practices that contributed significantly to the recession, the idea of holding people – not just companies – accountable for corporate wrongdoing has become a point of contention, both in the public eye and the justice community.

In September, the Justice Department responded with a memo encouraging judges and prosecutors in corporate criminal cases to shift their case-building focus onto individuals, rather than the company as a whole.

“Such accountability is important for several reasons: it deters future illegal activity, it incentivizes changes in corporate behavior … and it promotes the public's confidence in our justice system,” read the guidelines, collectively known as the Yates memo (for its author, Deputy Attorney General Sally Yates).

This isn’t a new impulse. President Theodore Roosevelt was trust-busting back in the early 1900s, limiting the industry dominance of tycoons including J.P. Morgan. Hundreds of Wall Street executives went to prison during the fallout of the Savings and Loan crisis in the late 1980s and early ’90s. Jeffrey Skilling, the head of now-defunct Enron, is serving a (reduced) 14-year sentence for his role in widespread accounting fraud that damaged that company and sent several people to jail.

But more recent, high-profile cases under former Attorney General Eric Holder’s administration have been settled by the company admitting wrongdoing and paying fines. These include banks involved in creating the housing bubble to General Motors’s years-long failure to repair a deadly ignition switch defect in millions of cars.

Many critics see this as an ineffectual corrective for companies that make billions in annual profits.

“We have descended too fully into the cesspool of crony capitalism when our most elite banks can commit what [Securities and Exchange Commission] investigations find to be fraud and still claim in filings … that they have ‘a strong record of compliance with securities laws,’ ” said attorney Bill Black, a former bank regulator and a leading critic of how the Justice Department has pursued major banks, in a 2012 interview with billmoyers.com

Why it's so hard to convict execs

But there is a rationale behind allowing companies to settle.

One is cost. “It can be very expensive and difficult to fight the DoJ on these matters,” says Solomon Wisenberg, a partner who heads up the white collar practice at Nelson Mullins Riley & Scarborough, a Washington law firm. In a lot of cases, it's cheaper to settle because of the potential impact of a case on a company’s stock value and profits. For example, Arthur Andersen, the accounting firm at the center of the Enron debacle, never recovered from the prolonged court battle – even though the Supreme Court ultimately overturned the firm’s conviction.

Second, holding executives culpable is simply harder to do. “These are fairly complicated sophisticated crimes, and it can be difficult to find a person that has all the requisite knowledge [for an individual conviction],” says Lucian Dervan, a professor at the Southern Illinois University School of Law. It’s much easier to implicate an entire company, he says, because prosecutors can use bits and pieces of information from separate employees to build their case.

“It’s a matter of the corporate structure insulating them,” Professor Dervan says. “Those at the top may have set the tone, but they don’t have the day-to-day knowledge.”

The Yates memo doesn’t offer anything revolutionary in the way of new tactics for prosecutors, Dervan says. But it does encourage them to “be thinking about the individual from Day 1” and warning corporations that they need to be prepared to cooperate. It instructs Justice Department lawyers not to resolve cases against entire corporations without having a “clear plan” to resolve those against individuals. It also warns strongly against making immunity for particular individuals a condition of settling a case with a corporation as a whole.

While it's not yet clear how those mandates will be followed, the Justice Department's FIFA investigation, for one, has been all about targeting officials. There is little indication so far of how the organization may be held culpable.

And VW could face jail time for some workers, as well as the possibility of record-breaking government fines. “Every case is different, but I think there’s a very high likelihood of criminal charges,” Dervan says.