Billion-dollar questions

It’s just one of many questions that jabbed itself into my brain yesterday after I read the creepy details of two lawsuits that alleged the onetime Boston broker raised about $1 billion from investors itching to do business with the con man of the century, Bernard Madoff.

Those civil lawsuits, by the Securities and Exchange Commission and the attorney liquidating Madoff’s business, both finger Jaffe as a man who knew or should have known what was going on. The SEC says Jaffe, a self-described Madoff victim, put at least $150 million in his own pocket along the way.

Jaffe was known in Boston and Palm Beach as Madoff’s big connection. He was the son-in-law of Boston philanthropist Carl Shapiro, one of Madoff’s oldest friends and earliest clients.

But a billion dollars, allegedly collected from about 150 clients, is an astounding amount of money. No wonder 78-year-old footwear tycoon Jerome Fisher wanted to punch Jaffe’s lights out when they ran into each other at swanky Mar-a-Lago in December - at least the way Donald Trump told the story.

So what was Jaffe, a hall of fame rainmaker or just a conduit for people eager to send their money to Madoff? I’ve yet to run into anyone who knew Jaffe and thought of him as anything other than a pipeline to Madoff. The majority of people I spoke with shortly after the Madoff story broke described Jaffe as something less than extraordinary and, frankly, not smart enough to be a key player in an elaborate financial con.

Whatever role he played, Jaffe became incredibly rich in the process. Rather than collecting commissions from his brokerage firm, Comad Securities, he was compensated directly by contributions to an investment account with Madoff, according to the SEC. Regulators claim that account somehow earned as much as 46 percent, while other investors were told they posted much smaller gains. That’s one way to get rich quick.

Jaffe allegedly got money out of his Madoff account by simply asking for specific amounts as gains in given periods. Big specific amounts.

A Madoff employee cooked up backdated investment transactions to account for the gain and then mailed out confirmations for trades purported to have taken place weeks or months earlier, the SEC lawsuit says. Those are the transactions that regulators say added up to at least $150 million.

Jaffe’s lawyers dismissed the claims made in the SEC lawsuit yesterday. “It is unfair, baseless in the law, and is inaccurate in its understanding of the facts and of Mr. Jaffe,’’ they wrote.

The most fascinating aspect of Jaffe’s business dealings doesn’t really have anything to do with business. How do you figure Jaffe’s relationship with his 96-year-old father-in-law? (The Shapiro family wasn’t saying anything yesterday.)

Shapiro, who has given many millions to worthy causes in Greater Boston, invested his fortune with Madoff and now appears to be out at least $400 million. In one of the story’s strangest turns, Shapiro wrote Madoff a check for $250 million weeks before the whole scheme collapsed.

Days after that collapse made front-page headlines, Shapiro and Jaffe sat glumly at a table at the Palm Beach Country Club, according to an account in The New York Times. Friends stopped by and tried to console them. What do you suppose they were thinking at that moment?

For months, Jaffe has tried to dummy up or dodge subpoenas from regulators such as William F. Galvin, the Massachusetts secretary of state. Now Jaffe will be stuck with the Sergeant Schultz defense. He knew nothing while all that money moved from his clients to Madoff and eventually disappeared.

That will be a hard story to sell if allegations about Jaffe’s compensation stand up in court. Life just got tougher for the billion-dollar man.

Steven Syre is a Globe columnist. He can be reached at syre@globe.com.