Lawyers have long complained that insider trading laws are a murky mess. Two cases that ended on Friday—one with a civil penalty, the other with a guilty verdict—are further proof of how inconsistent the standards can be.

The alleged wrongdoing was similar—a tip about an impending merger—as were the ill-gotten gains: about $250,000 versus $300,000.

But Robert Carr, the former chief executive of Heartland Payment Systems Inc., got off with paying a $250,628 civil fine.

By contrast, former S&P analyst Sebastian Pinto-Thomaz was convicted by a federal jury in Manhattan of two counts of conspiracy to commit securities fraud and two counts of securities fraud. He's looking at hard time behind bars, plus a fine of up to $5 million.

Why such different outcomes?

From the outside, it's hard to say—and of course prosecutors always make discretionary calls about the charges they bring.

But insider trading—which isn't expressly defined by statute—is extra-squishy. As Columbia Law School professor John Coffee Jr. reminded a House Financial Services subcommittee earlier this month, it's a common law crime.

“To date, the law of insider trading has been solely the product of judicial law-making,” Coffee said. “There is general agreement today that the law of insider trading has grown overly complex and technical. As a result, it is hard for the public to understand its logic or for practitioners to give advice with respect to the scope of the prohibition.”

Coffee was testifying in support of legislation introduced by Rep. Jim Himes, D-Connecticut, that would define and prohibit insider trading. And indeed, these two most recent cases help illustrate why brighter lines would be helpful for defendants and prosecutors alike.

Carr, who is in his mid-70s, was busted by the U.S. Securities and Exchange Commission for tipping his 63-year-old girlfriend about his company's impending acquisition by Global Payments Inc.

According to prosecutors, Carr was neck-deep in the scheme. He allegedly gave the girlfriend, Katherine Hanratty, $900,000 to buy stock in Heartland shortly before it was acquired by Global Payments for $4.3 billion —a deal in which Carr as CEO was intimately involved.

In an email to Hanratty, he mentioned the acquisition's expected closing date and share price. Hanratty made more than $250,000 when she sold her newly-acquired shares.

Carr's lawyers from Ropes & Gray countered that their client in the email was merely sharing details of his day, not intending to tip Hanratty off. The “one statement concerning his meeting with Global—buried amidst romantic pleasantries and commonplace details of the couples' meals, bedtimes, and plans with friends, all shared with a significant other—is the only 'tip' of material non-public information specifically alleged in the complaint,” they said.

(Er, doesn't it only take one tip?)

Carr's lawyers also said that when he gave Hanratty $1 million right before the merger was announced, he had no idea she would use $900,000 of it to buy stock—an assertion that the SEC disputed. Also, defense counsel said that the SEC “fails to identify any specific personal benefit Mr. Carr received” in exchange for the tip.

Hanratty previously agreed to pay a $528,608 fine to settle the SEC charges.

Carr was represented by Ropes & Gray's Michael McGovern, who co-chairs the firm's government enforcement practice, plus partners Jeremiah Williams, previously a senior counsel in the U.S. Securities and Exchange Commission's enforcement division, and Colleen Conry, a former senior litigation counsel in the fraud section of DOJ's criminal division.

In all, they seem to have gotten their client an excellent deal. And the $251,000 fine, while not inconsequential, hardly seems ruinous to a person who had $1 million sitting around to give to his girlfriend.

Pinto-Thomaz, on the other hand, faced much harsher consequences for what in some ways seems like less egregious conduct (i.e. he didn't give anyone a small fortune to fund an illicit stock purchase.)

He's young—only 32 years old. As a credit ratings analyst at Standard & Poor's, he was privy to information about pending deals—in this case, Sherwin-Williams Co.'s $9.3 billion acquisition of rival Valspar Corp.

Perhaps by hitting him hard, prosecutors wanted to send a message to the legion of lawyers and investment bankers and accountants and support staff who work on deals: Keep your mouth shut.

After a seven-day trial before U.S. District Judge Jed Rakoff in Manhattan, a jury on April 26 promptly found Pinto-Thomaz guilty of tipping two friends about the paint merger.

Prosecutors said that during a haircut, Pinto-Thomaz told Abell Oujaddou—a Manhattan hairdresser whose clients have included Meryl Streep, Kate Winslet and Robert De Niro—about the deal. Pinto-Thomaz and his mother were allegedly friends with Oujaddou.

According to prosecutors, Oujaddou pocketed $192,000 from purchasing Valspar stock, and gave Pinto-Thomaz $7,500 of his proceeds.

Pinto-Thomaz also allegedly tipped his friend Jeremy Millul, a jeweler who did business with his mother. He made $106,806 when he sold his Valspar stock. Pinto-Thomas apparently got nothing tangible in exchange for the tip.

Both Oujaddou and Millul pleaded guilty to conspiracy to commit securities fraud.

At trial, Pinto-Thomaz claimed it was actually his mother who blabbed about the merger, not him. But the jury didn't buy it.

 “Sebastian Pinto-Thomaz stole confidential information from his employer and passed it to two men he had known for years—and he did it for his own personal benefit,” U.S. Attorney Geoffrey Berman said in a news release. “While the defendant attempted to blame his mother for this conduct at trial, as a unanimous jury found, it was Pinto-Thomaz who committed insider trading.”

Pinto-Thomaz is represented by Henry Mazurek, a criminal defense partner at Meister Seelig & Fein who has scored some high-profile acquittals (including a crazy case in 2015 involving Orthodox Jewish rabbis charged with kidnapping and torturing men to force them to agree to divorce their wives).

In an email, Mazurek said, “We are disappointed by the verdict today but vow to continue to fight to overturn the verdict on appeal. We believe the judge erred in excluding a critical defense witness and also for broadly defining personal benefit in insider trading cases to include mere friendship.  We believe the law requires much more.”