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President Obama introduces Penny Pritzker as his nominee for Secretary of Commerce. (AP Photo/Carolyn Kaster.) Ad Policy

Did you know that in the early 1970s, the Internal Revenue Service investigated the Pritzker family, whose scion Penny Pritzker has just been tapped by President Obama to become Secretary of Commerce, because their Hyatt Corporation was paying no taxes? And that in the course of the inquiry, an IRS statement quoted an informant with access to the records of the offshore bank where they hid their assets that the family, “through their Hyatt Corporation, received their initial backing from organized crime”?

Did you know that this particular financial institution, Castle Bank & Trust of the Bahamas, was founded by a veteran of the wartime spy agency the Office of Strategic Services who specialized in creating front organizations for the CIA, and helped launder funds for attempts to overthrow Fidel Castro? That Castle operated by arranging for a Miami bank controlled by associates of mobster Meyer Lansky to accept the original deposits, which it then passed on to Castle with only code numbers, but not names, attached?

Did you know that the IRS dropped a major investigation of Castle in 1977, according to The Wall Street Journal, at the behest of the Central Intelligence Agency?

And did you know one of the bank’s cofounders, the late Burton Kanter, was on the board of the Hyatt Hotels Corporation, and that—as The Kansas City Times discovered in a 1982 Pulitzer Prize–winning investigation following the collapse of a shoddily constructed skywalk that killed 114 at a Hyatt in 1981—the Pritzkers were Castle Bank’s largest depositors?

Did you know that Kanter was the Pritzker family’s tax lawyer, and was able to reduce the IRS bill when patriarch A.N. Pritzker died in 1986 from the $150 million the government said the family owed for his estate only $9.5 million? (Or that family itself claimed his estate only possessed $3,000 in taxable assets?) Did you know that, twenty-four years later, a tax judge ruled that Kanter was the “architect” of “a concerted effort” to profit from kickbacks involving the siphoning off of funds managed by insurance companies? (The hustle included the invention of sham companies—“pure tax avoidance vehicles,” the judge said—the destruction of documents, and “implausible” and “incredible” testimony by Kanter.) This 2007 article by David Cay Johnston on the “overwhelming objective evidence” that led another tax judge to uphold the conviction places the Pritzker family at the center of the scam. And it notes that Kanter’s tax returns, now public, “show he never paid any significant tax. Yet he amassed a fortune big enough at one time to make him a credible bidder for the Miami Dolphins football team.”

Did you know that A.N. publicly denied ever using the legal services of fixer Sidney Korshak, for decades the notorious transit point between the mob and legitimate business interests in Chicago, before Korshak admitted to the Securities and Exchange Commission that he was in fact the family’s labor lawyer? That a Los Angeles Police investigator’s report said A.N. was “[c]losely connected with members of the Capone syndicate, Tony Accardo, and other underworld characters? It is believed by the undersigned that Pritzker may be active locally, as a front for Eastern hoodlum money to be invested in the Los Angeles Area”? That A.N.’s law partner Stanford Clinton was general counsel for the notoriously mob-connected Teamsters pension fund?

I got much of this stuff from Gus Russo’s voluminous book Supermob: How Sidney Korshak and His Criminal Associates Became America’s Hidden Power Brokers. It’s an over-the-top book, hanging all sorts of claims on insinuation and guilt by association, so I’ve only included here the stuff I consider solid. And let’s respectfully dissent from Shakespeare, who wrote in the Merchant of Venice, “The sins of the father are to be laid upon the children”: Penny is not responsible for the dodgy practices of her grandfather. It’s not her fault her late Uncle Jay, who bought Hyatt in 1957, deployed it as a platform for innovative “asset management” financial engineering that kept the family at arms’ length regarding risk and responsibility (nowadays with the assets coming from Chicago taxpayers). She can’t be held responsible for the way Jay, back before that, benefited from very questionable deals arising from his tenure in the Justice Department’s Alien Property office, responsible for assets seized by the government. Nor can she be held responsible for the mob money allegedly behind the expansion of Hyatt in the first place. “Behind every fortune lies a great crime,” is the Balzac quote Russo uses to introduce the Pritzker family in his book; but that’s not Penny’s fault either, is it?

But certain patterns still obtain. It is one of the most crucial stories for understanding our age: how tax-avoidance strategies of a previous generation that might have landed you in court are now legal—which does not make them any more ethical. In fact, it may make them less ethical—precisely because third-gen scions like Penny, born in 1959, have entered into the political establishment, where their representatives, their latter-day Korshaks and Kanters, do their laundering in the halls of government instead of in Las Vegas hotel room meetings with associates of Tony Accardo. The scumminess is the same, or, really, worse; as Charlie Savage wrote this week in The New York Times, “Republican senators are likely to be interested in the Pritzker family’s reputation as innovators in the use of offshore trusts and foreign bank secrecy laws to shelter their wealth from income, capital gains and inheritance taxes. Even after tax loopholes were closed, the family’s trusts were grandfathered in and it kept benefiting from them.” As well the Republican senators should. And, hell, Democratic senators, too.

The crime is what is no longer a crime. Indeed, wrote David Cay Johnston, Burton Kanter regarded himself as the nation’s premier expert at “legally eliminating taxes.” He even proudly documented his techniques in legal journals.

Savage asked the White House what made Penny Pritzker suitable for a confirmation fight she was not qualified for in 2008. The spokesman responded that back then, she “had an ongoing obligation to oversee her family’s restructuring of assets to separate out the interest of various family members.” Now, that task has apparently been completed, or, as “a White House official involved in vetting her” put it, “they had since completed dividing up their finances.”

Got that? It took lawyers four years to figure out how to divest her from the sleaze. And that’s what makes her qualified for the job—a job not unrelated to the devising and interpretation of tax policy itself. And, not incidentally, a job concerned with subjects like this:

Tax evasion by individuals with unreported offshore financial accounts was estimated by one IRS commissioner to be several tens of billions of dollars, but no precise figure exists. IRS has operated four offshore programs since 2003 that offered incentives for taxpayers to disclose their offshore accounts and pay delinquent taxes, interest and penalties. GAO was asked to review IRS’s second offshore program, the 2009 OVDP. This report (1) describes the nature of the noncompliance of 2009 OVDP participants, (2) determines the extent IRS used the 2009 OVDP to prevent noncompliance, and (3) assesses IRS efforts to detect taxpayers trying to circumvent taxes, interests and penalties that would otherwise be owed. To address these objectives, GAO analyzed tax return data for all 2009 OVDP participants and exam files for a random sample of cases with penalties over $1 million; interviewed IRS Offshore officials; and developed and implemented a methodology to detect taxpayers circumventing monies owed.

That’s the abstract to a paper published two months ago and distributed by the Commerce Department’s National Technical and Information Service. I would give far more than a penny to hear Pritzker’s thoughts about that.

Read Part One of Rick Perlstein’s Pritzker commentary.