In his and Robert's letter, Jay made clear that the family trusts were not to be broken up until the law governing trust perpetuities required it, which one source suggests might not be until 2042. Jay also made explicit his plans for succession. Tom would take his place at the head of the family business. A published expert on 11th- to 15th-century Tibetan art, and a close friend of the Dalai Lama's, Jay's oldest son had worked in the family business since getting law and business degrees from the University of Chicago in the late 1970s. Penny and Nicholas would work with Tom as, in effect, vice-chairmen of the Pritzker operations. The daughter of Jay and Robert's younger brother, Donald, who died in 1972, Penny is the first female Pritzker to rise to the top of the family empire. Now 43, Penny is a triathlete and a Harvard graduate, with law and business degrees from Stanford. Nick, now 57, is probably the most charming and outgoing of any Pritzker, after Jay. Although he was Jay and Robert's cousin—their uncle Jack's son—he was closer in age to Jay's children and had started to work for the family business in 1975. As Jay saw it, this was the triumvirate that would lead the Pritzkers into the new century. Jay made it clear that he expected his children and nieces and nephews to "feel morally bound" to follow his wishes. "Since our generation primarily created the wealth our Family possesses, within the limits imposed by the law, we are entitled to express our wishes as to the disposition of that wealth," Jay wrote. Attached to the letter was a separate memo. It was, some say, Jay's peace offering, a gesture he hoped would help keep the family happy. In it, he outlined a series of lump-sum payments and allowances that would be given to each member of the fourth generation and to Nick. The payouts had been put in place around 1990, but Jay increased the amounts. Starting when they graduated from college, each of the cousins would now get a yearly stipend—paid retroactively—that would begin at $100,000, after taxes, and climb to $1 million a year at the age of 40. On top of that, there would also be lump-sum payments for having passed key points in their lives—graduation from college, reaching the age of 30, and so on. By their 45th birthdays, it is said these payments would add up to a tidy $25 million per cousin, also after taxes. One doesn't have to read between the lines to understand that Jay was worried about giving this kind of money to the next generation. "We earnestly hope that providing [this] money from the Trusts will not destroy the family ethic," he wrote in the letter, "and it is our belief that in some circumstances making excessive amounts available could have that effect." After Jay spoke and the letter was read, everyone seemed happy. No one raised any objections. "There was no dissent," says a friend of the Pritzkers'. It appeared that Jay's gambit to buy peace in the family had worked.

In the history of American business, there are probably few men who were as pragmatic about making money as Jay Pritzker. He did not buy companies out of ego, or because they were in fashionable industries, or because they were well-known names. He bought them only if he believed they could make him a profit. In a career spanning nearly 50 years, Jay bought and sold more than 200 companies and financed the start-up of many others. Most of these were companies that few people have ever heard of—nuts-and-bolts manufacturing companies such as the Amarillo Gear Co. and Darling Store Fixtures. He would buy them if he thought they were undervalued by the market, or if their tax structures were such that, when combined with other companies in his empire, they would help him reduce—and sometimes eliminate—the taxes to be paid to the federal government. "Jay was always looking for an angle," says one banker who knew him well. "A tax angle, or a value angle. Something that others didn't see." He was the kind of man who could sit in a hotel coffee shop near Los Angeles International Airport, as he did one day in 1957, see that it was bustling, discover that the hotel had no vacancies, and see a deal. The coffee shop was called Fat Eddie's, and the hotel was Hyatt, named after its owner, Hyatt von Dehn, and Jay bought both that afternoon for $2.2 million, writing his offer price on a Fat Eddie's napkin. His bet was that business executives would want to stay at luxury hotels near major airports, and he turned out to be right. Today the Hyatt chain is said to be worth anywhere from $5 to $7 billion. Among hard-core financiers, Jay is considered to have been perhaps the greatest deal-maker of his day, although he was almost completely unknown to the general public. Few people, for example, knew that he controlled Braniff Airlines for a time in the 1980s, or McCall's magazine, which he bought in 1973 and then sold in 1987, or Ticketmaster, which he bought in 1982 and sold in 1993, or Levitz Furniture. Or that his family owns a quarter of Royal Caribbean Cruises and helped found Tenet Healthcare Corporation, the second-largest hospital owner in the country. Jay hated publicity and managed to avoid it even when involved in wildly controversial deals—using a partnership called Resource Holdings for an unsuccessful hostile run at the ITT Corporation in 1984, for example, and a partnership called GKH to represent him in 1989 in a failed bid by First Boston to break up RJR Nabisco.