Editor’s Note: Errol Louis is the host of “Inside City Hall,” a nightly political show on NY1, a New York all-news channel. The opinions expressed in this commentary are his own. View more opinion articles on CNN.

CNN  — 

The guilty verdict against Roger Stone, a longtime adviser to President Donald Trump, is a devastating turn of events — perhaps the final chapter — in the storied life of a political trickster. It’s also a cautionary tale about the dark corners of democracy, where the limits of law and morality are frequently tested, traded, and violated.

Stone knows the rules of this world better than anybody. “You can call me a dirty trickster, you can call me a prankster, you can call me anything you’d like,” he told Rolling Stone in 2018. “I’ve never done anything that hasn’t been done by my contemporaries in the political strategist business. I do fight hard for my clients, but I’ve never crossed the line into illegal activity.”

That “crossed the line” boast vanished this week, when a jury found him guilty on seven counts of witness tampering, making false statements and lying to Congress at a fateful 2017 hearing about his connection to Wikileaks during the 2016 campaign.

Who is Roger Stone?
Who is Roger Stone?
00:50 - Source: CNN

Stone had publicly claimed to have a back channel to Julian Assange and the shadowy Wikileaks operation, and to know in advance about stolen emails that were released at key moments in the 2016 campaign, timed to help Trump by inflicting maximum harm on Hillary Clinton and the Democratic National Committee.

Stone’s connection was (he claimed in classic Roger Stone style) a slightly shady but perfectly legal arrangement. Special counsel Robert Mueller thought otherwise and indicted Stone for lying about the nature of those connections.

The jury agreed. The Wikileaks caper turned out to be one dirty trick too many.

Stone gleefully cultivated the image of, as he once put it, “a libertarian and a libertine,” the kind of man prepared to take on sketchy assignments that other operatives would shun as too risky or immoral. He drove expensive Jaguar sedans, dressed impeccably in custom-tailored Saville Row suits, frequented sex clubs and got bounced from the 1996 presidential campaign of Bob Dole when the National Enquirer published an ad seeking group sex partners to join him and his wife in a liaison.

He actively cooperated with filmmakers on “Get Me Roger Stone,” a movie that detailed his long history of skullduggery. His “greatest hits” include making phony donations to a Democratic candidate in the 1970s in the name of a made-up group, the “Young Socialist Alliance,” and then leaking the information to a newspaper to smear the Democrat as having ties to the far left.

In 2000, during the Florida recount to settle the presidential race, he coordinated the so-called “Brooks Brothers riot” that shut down the recount. (The Miami-Dade County Florida Board of Elections voted to stop the ballot counting until further notice — and soon after a Supreme Court decision ended the race, making George Bush president.) In 2010, Stone was campaign manager for the gubernatorial bid of Kristin Davis, the “Manhattan Madam” who once ran a high-end prostitution ring.

More recently, he published books promoting outlandish conspiracy theories about the Bush and Clinton families. And for years, he gave advice to then-businessman Donald Trump, telling anybody who would listen that Trump could become president.

I frequently interviewed Stone about political strategy, Florida politics, the reasons for Trump’s rise and men’s fashion (about which he happens to be brilliant). He was an undeniably colorful character in the political circus and might yet emerge from what is the biggest setback in his life.

Trump-haters might imagine that Stone, facing up to 20 years in prison, might be in a prime position to share damning information about the President. That’s wishful thinking.

The problem that sank Stone at trial was his many years of posturing as the bad boy who would twist the truth and break the rules whenever necessary. Having established a reputation for shadiness, it became difficult for Stone to convince a jury that he was, for once, completely on the level.

That same issue will come up if prosecutors try to flip Stone and get him to reveal anything damaging about Trump. Who would believe him?