Mitt Romney and the Junk Bond Felon Michael Milken

6/24/12 10:07 AM EDT

The Boston Globe is out with the third in a hat-trick of probing and, for Mitt Romney, blistering stories from broadsheets this week about the presumptive Republican nominee's Bain Capital tenure - this one focusing on a specific deal he did with "junk bond king" and symbol of Gordon Gekko-type activity for his critics, Michael Milken.

This deal was in the 1980s, and involved Romney's hunt for $300 million in financing for a deal, which Milken provided:

What transpired would become not just one of the most profitable leveraged buyouts of the era, but also one of the most revealing stories of Romney’s Bain Capital career. It showed how he pivoted from being a relatively cautious investor to risking his reputation for a big payoff. It is one that Romney has rarely, if ever, mentioned in his two bids for the presidency, perhaps because the Houston-based department store chain that Bain assembled later went into bankruptcy.

But what distinguishes this deal from the nearly 100 others that Romney did over a 15-year period was his close work with Milken’s firm, Drexel Burnham Lambert Inc. At the time of the deal, it was widely known that Milken and his company were under federal investigation, yet Romney decided to go ahead with the deal because Drexel had a unique ability to sell high-risk, high-yield debt instruments, known as “junk bonds.”

The Obama campaign has criticized the deal as showing Romney’s eagerness to make a “profit at any cost,” because workers lost jobs, and challenged Romney’s assertion that his business background best prepares him for the presidency. Romney, meanwhile, once referred to the deal as emanating from “the glorious days of Drexel Burnham,” saying, “it was fun while it lasted,” in a little-noticed interview with American Banker magazine.

The “glorious” part, for Romney at least, was that he used junk-bond financing to turn a $10 million investment into a $175 million profit for himself, his partners, and his investors. It marked a turning point for Romney, according to Marc Wolpow, a former Drexel employee who was involved in the deal and later was hired by Romney to work at Bain Capital.

“Mitt, I think, spent his life balanced between fear and greed,” Wolpow said. “He knew that he had to make a lot of money to launch his political career. It’s very hard to make a lot of money without taking some kind of reputational risk along the way. It’s just hard to do. It doesn’t mean you have to do anything illegal or immoral, but you often have to take reputational risk to make money.”

The story is long, and some of the most interesting elements are the fact that Milken was slapped with the insider trading charges that ultimately led him to being jailed after a guilty plea just as the deal with Bain was being cemented:

Some clients feared being tainted by scandal, but Romney stayed loyal: The deal was too important.

“We did not say, ‘Oh my goodness, Drexel has been accused of something, not been found guilty,’” Romney told the Globe years later. “Should we basically stop the transaction and blow the whole thing up?”

The less-sexy elements of the piece relate to the merger of department store chains into Stage Stores, which later filed for bankruptcy and which has been one of the cases highlighted by Democrats as an example of how Bain profited even if some of the companies it took over did not.

This is not a freshly-unearthed case - the authors of the book "The Real Romney," one of whom co-wrote this Globe piece, write about the Milken deal in their book. This is also the way leveraged buyouts work - complicated, multi-dimensional deals.

But the chances of this story making it into ad copy or direct mail are high, with Milken's very-recognizable name attached and the Globe's reporting quoted.

Republicans have been relieved that the messaging around Romney's business career has remained, as Alex and John Harris put it, a "muddle" so late in the year. The bet from the Democrats is that there is seepage over time, filling out the frame of Romney as too risky to take a chance on.