If not for their involvement with Trump, and if not for his win in 2016, Cohen and Manafort might have never faced serious scrutiny, much less prison time. Each represented a sort of all-American success story. Cohen was just a kid from Long Island who, despite attending perhaps the nation’s worst law school, ended up as a millionaire (thanks to investments in real estate and the taxi business) and a close associate of the famed businessman Donald Trump. Manafort, the son of a small-town mayor, lived even more fabulously, raking in tens of millions of dollars as a lobbyist and jetting around the globe.

By the time he volunteered to work on Trump’s campaign, Manafort was broke and already under law-enforcement scrutiny, but associates thought his decision to go run a presidential campaign was a colossal blunder. Knowing how he often worked along the edges of what was legal, they figured helming a political campaign, and especially one as obsessively covered as Trump’s, was practically taunting the media and the feds to turn up dirt on him. In retrospect, those friends were right.

The public still doesn’t know exactly how Cohen got snared, but the investigation was apparently triggered when Mueller passed evidence to the U.S. attorney in the Southern District of New York. It’s likely that the things that attracted prosecutors’ attention were the two hush-money arrangements Cohen made with women who alleged sexual affairs with Trump. It’s unclear whether Cohen arranged other such payments on his boss’s behalf before entering politics, but that wouldn’t have violated any laws.

In that sense, the day Trump won the presidency was the worst day of their lives. The second-worst day was the day that Trump fired James Comey, eventually leading to Mueller’s appointment as special counsel. As Jack Goldsmith writes in The Weekly Standard, “Manafort and Cohen would likely be free today had the Russia investigation stayed within traditional Justice Department channels using traditional Justice Department resources. But once [Deputy Attorney General Rod] Rosenstein appointed Mueller, the grinding logic of a single-minded, heavily-resourced, subpoena-wielding independent prosecutor pursuing every avenue toward a determined end took over.”

How the Manafort indictment gave bite to a toothless law

Like Cohen and Manafort, who apparently expected to keep getting away with their tricks indefinitely, Trump seems perplexed that prosecutors are bothering to go after Manafort and Cohen for such piddling offenses as bank fraud and campaign-finance violations. Trump said he felt “very badly” for Manafort, dismissing the charges against him as old, which isn’t much of a rebuttal. The president was less complimentary of Cohen, deriding him as a bad lawyer and a weakling, yet he also added this:

Michael Cohen plead guilty to two counts of campaign finance violations that are not a crime. President Obama had a big campaign finance violation and it was easily settled! — Donald J. Trump (@realDonaldTrump) August 22, 2018

The second part of this refers to a fine levied against the 2008 Obama campaign. Looking at these specific cases, the crucial differences are that the Obama campaign wasn’t accused of a conspiracy to violate the rules, and the candidate himself wasn’t accused of directing the conspiracy, as is the case with Trump and Cohen. More broadly, what Trump seems to mean is that campaign-finance violations are typically dealt with as a simple regulatory matter: If you make a mistake, you pay a fine and the matter is resolved.