Here's a glimpse of Toomey's background trading derivatives and pushing the market deregulation that some blame for playing a leading role in the financial meltdown. Until the mid-1980s, derivatives—financial products whose value is derived from the value of a different, underlying asset, like a house or a bushel of wheat—were only legally in force if one of the two parties owned or had promised to buy the underlying asset. In order for the government to enforce the deal, one party effectively had to be insuring something—"hedging" against economic risk. You could still trade derivatives if neither party owned the asset, but you couldn't use the court system to adjudicate these purely speculative wagers. At the time, the vast majority of derivatives trading took place on exchanges like the Chicago Mercantile futures exchange. The exchanges functioned as private trading clubs—and they had various internal rules designed to ensure traders could pay off their bets.

That all changed in 1986, when the UK passed a law—the Financial Services Act—that essentially made all derivatives trades legally enforceable, even if neither party in the transaction owned the underlying asset. The US followed suit soon afterwards, issuing a steady stream of regulatory exemptions that made one type of derivative after another legally enforceable. Lynn Stout, a derivatives expert at UCLA Law School, says the UK law and "how much money they were making in the City [of London]...spurred Wall Street to push for similar legal changes in the States." Some people—like Brooksley Born, who went on to head the Commodity Futures Trading Commission from 1996 until 1999—argued against the changes [9]. They were ignored.

Suddenly, investors could gamble on almost anything—and instead of the rules-based exchanges to enforce the deals, the government would do it—no questions asked. It was as if world governments had suddenly agreed to enforce every handshake bet you make with a buddy. This was the change that would allow a few hedge funders, years later, to place multibillion dollar bets against the US housing market and know that their counterparties would have to pay up—or go broke trying. Derivatives trades naturally exploded—and Toomey was right in the middle of the boom. The market "became quite sophisticated," Toomey told [8] Derivatives Strategy magazine in 1999. He was "dealing in various currencies, all kinds of interest rate and currency-related derivatives—options, swaps, forwards and so on." In the five years after the UK law went into effect, the size of the global derivatives market more than quintupled [10]. In 1991, when Toomey left the derivatives business, the notional value of global derivatives contracts reached nearly $4.5 trillion, up from $865 billion in 1986.

In the years that Toomey ran sales and trading at Morgan Grenfell, the company brokered a number of interest rate swap deals with municipal governments (called "local councils") in the United Kingdom. (Although Toomey was based in New York, he also managed the firm's derivatives business [11] in Tokyo and London.) In the UK, municipalities are generally funded by the central government. But under Margaret Thatcher, their funding had become sharply limited, and many were searching for alternative, off-the-books methods of funding their operations. Morgan Grenfell and other derivatives dealers stepped into the breach, brokering deals with and between various municipalities. Interest rate swaps—where the two parties in effect bet on whether interest rates are going to go up or down—were especially popular. Many of these deals were in effect loans—the councils would receive large sums up front and pay them back over time based on interest rate differences. Of course, if the interest rates went the wrong way, you could end up owing far more than you initially anticipated.

Soon, some of the councils ended up deep in the red—and the British House of Lords "solved" the problem by ruling that it was illegal for the local authorities to have entered into the swap deals in the first place. The decision triggered a wave of litigation—including a watershed suit involving Toomey's firm. In that case, Morgan Grenfell v. Welwyn Hatfield District Council, the court ruled that even though interest rate swaps could be used for wagering, they should generally assumed to be "not gaming or wagering," but instead "commercial or financial transactions to which the law will in the absence of some other consideration give full recognition and effect." That was the final blow to the old concept of legal unenforceability, and it sent a signal to derivatives brokers that courts would step in to enforce their contracts if necessary. And that would make some people dealing in interest rate and currency swaps—like Toomey—very rich.

During the campaign, Toomey has referred to the products he worked with [12] as "non-risky" "common derivatives," different from the "toxic" mortgage-backed derivatives that some believe caused the financial crisis. "That's not true," says Michael Greenberger, a professor at the University of Maryland and former CFTC official. "It just so happens that the 2008 meltdown involved credit default swaps, but interest rate swaps and currency swaps can be as risky as anything else. These swaps are very, very risky."

Toomey's defense ignores the recent history of interest rate swaps, which led to fiscal problems for many American towns, cities, and states across the country in recent years. The US never had a House-of-Lords-type decision forbidding municipalities from making these sorts of deals. So just as Morgan Grenfell had in the '80s, US banks pressed local governments to agree to swap deals to bring in extra revenue. And this time, many of the banks allegedly paid kickbacks [13] on the deals. (The kickbacks are the subject of an ongoing federal investigation.) In Pennsylvania alone, 107 school districts reportedly [14] entered into swap deals—"gambling with the public's money," according to the state's auditor general. Some have since paid millions of dollars to Wall Street banks to get out from under the deals. Chicago, Denver, Kansas City, Missouri, Philadelphia, Massachusetts, New Jersey, New York, and Oregon all recently lost money on similar swap deals, according to the [14]Wall Street Journal [14].

Problems stemming from the sorts of derivatives Toomey traded date back before the crisis, too. And they don't just affect governments. In 1998, the Fed had to organize a $3.6 billion bailout of Long Term Capital Management, a highly-leveraged hedge fund whose collapse threatened the stability of the global financial system. LTCM had gotten in trouble trading the same products that Toomey made his money working with—currency and interest rate swaps. LTCM wasn't the only example. The bankruptcies of Orange County, California, in 1994 and the British bank Baring's in 1995 (an event dramatized in the 1999 Ewan McGregor film Rogue Trader [15]) were also driven by failed derivatives deals. Later, Larry Summers, who went on to become Obama's top economic adviser, reportedly lost $1 billion [16] on interest rate swaps as president of Harvard University.