At the same time that John Kennedy was trying to cope with Anthony Radziwill’s devastating illness, he was also taking meetings with other members of his generation in the offices of Park Agency, Inc., the family’s team of business managers in New York. The Kennedys were in the process of attempting to restructure and redistribute their tremendous wealth. Of course, because of their mother’s marriage to Aristotle Onassis, John and Carolyn were more than set financially for life, with each being worth as much as maybe $50 million by 1998. “It was hard to imagine how much money they had,” said one of their cousins, laughing. “We would think, wow … John’s that rich but yet doesn’t spring for dinner?” Still, despite his tremendous wealth, John attended all the meetings at Park Agency, Inc.—and there were many of them—feeling that even though he didn’t need the additional money, he was entitled to it, as was his sister; he wanted to be a part of the proceedings. Caroline, though, didn’t attend a single one. When it came to discussing money with her cousins, she drew a line in the sand. She sent her husband to one of the meetings, and he then reported back to her that John had it covered. The Schlossbergs could safely stay out of it.
Prior to these meetings in 1998, most of the Kennedys of the third generation had their inheritances completely tied up in trusts and other entities that had been created with tax strategies in mind; it all made it difficult for them to access any funds, even for emergencies. In a sense, it wasn’t exactly what the patriarch had had in mind. Back in 1940s, Joseph P. Kennedy used to tell his wife, Rose, “I’m making all this money so that my children don’t have to, so they can go into public service.” In other words, he wanted at least his own children to be able to access their cash, and probably, if he had been asked, he would have liked his grandchildren to have the same access. However, after RFK died in 1968, Rose Kennedy began to clamp down on the way the family’s fortune was being spent.
By 1970, each of the families—Kennedys (Jackie’s, Ted’s, and Ethel’s), Shrivers, Smiths, and Lawfords—were allocated about $150,000 a year, a sizable amount for the times with the average per capita income being $9,350. However, Ethel’s Hickory Hill was an expensive enterprise. Unlike, for instance, Sargent and Eunice, who had their own thriving philanthropy to finance Timberlawn (their estate from which much of their youth charity was run), Ethel was entirely dependent on the Kennedys’ largesse. She was also having trouble accessing her own family’s wealth, which had been put into complex Skakel investments that would frustrate and exasperate her throughout the seventies and all the way into the nineties. The third generation—her children and their cousins—also had trouble accessing trust funds and annuities as they got older, which is why some of them ended up finding their own ways of making money. Joe Kennedy II started Citizens Energy, for instance, and when his brother Michael took over the company (when Joe became a congressman), it continued to turn a huge profit and provide many millions of dollars for both of them. Others weren’t as lucky. For instance, Newsweek reported that Bobby Jr. and his wife, Mary, might be forced to sell their house in Bedford because it was no longer sustainable. “Compared with his wealthier relatives, Bobby and his siblings were paupers,” Newsweek noted. “His father had spent much of his inheritance on his 1968 presidential run. What was left went largely to his widow, the remaining amount divided among the eleven children.” It wasn’t true that RFK had used his inheritance to finance his presidential run, but the essence of what Newsweek reported of Bobby’s siblings having to figure out their finances was true. “Of course, it overstates it to say that any of the Kennedys were ever paupers as Newsweek suggested,” said the family’s attorney Benedict F. Fitzgerald Jr. in an interview in 2012. “But prior to 1998, many of them did have to find ways to make a living in order to augment trust funds that were not easily accessible to them.”
Things changed dramatically for the next generation in 1998 when the Kennedys decided to sell off the Merchandise Mart in Chicago—a family enterprise bought by the senior Joe in 1945 for $12.5 million—as well as other massive holdings. This financial reworking was the purpose of all those meetings in 1998 of Kennedy heirs at Park Agency, Inc. The properties that were to be sold consisted of 5.3 million square feet of office, retail, and showroom space—including the Apparel Center in Chicago, the Washington Design Center, and the Washington Office Center, both in Washington, D.C. All of it was sold for $625 million, and the sale was made for one reason: to once and for all seed the lives of the next generation, or as the Chicago Tribune put it, “The transaction fulfills a plan by the Kennedy family to sell real estate to satisfy the goals and financial needs of a growing number of family members.” A small percentage of the wealth—which would still be managed by Park Agency, Inc.—would be split among all the members of the next generation, the children of Jack, Bobby, Teddy, Eunice, Pat, and Jean. They, in turn, would be free to distribute it to their offspring as they saw fit. Suffice it to say, this 1998 business maneuver would serve to finance a whole generation of Kennedy heirs, and the one after that one, too … and likely many more to come.
Pretty much every member of the next generation of Kennedys—and that’s twenty-seven cousins, Kennedys, Lawfords, Smiths, and Shrivers—immediately received about $10 million each from the Chicago sale to do with what they liked, and many more millions—don’t forget, the sale was for $625 million—which would be invested for them. Today, some of the Kennedys, such as Ted’s children, Teddy and Patrick, are said to be worth about $20 million each, most of it from the sale, but also from inheritances. Bobby and Joe Kennedy are today worth $50 million—about $10 million liquid of which came from the Chicago sale and the rest from their own lucrative work: Joe’s with Citizens Energy and Bobby’s as an environmental attorney. While the wealth of the new generation is complicated in that they all have their own accountants and have invested in their own ways, one thing is certain: if not for the 1998 sale, the Lawfords and Smiths, for instance, and some of the Shrivers, too, would have been in trouble. (Maria Shriver would never have to worry, though; her marriage to Arnold Schwarzenegger set her up nicely.)
Ethel Kennedy’s present wealth is estimated at “just” $50 million, but a lot of that is old Skakel money she was finally able to access in the 2000s and not from the Chicago sale. Both she and Ted, whose estate was also estimated at $50 million, decided not to profit from the sale of the Merchandise Mart, trickling any of their parts down to their children.
Ethel’s son Christopher Kennedy is quite wealthy after having run the Merchandise Mart as its president and later a top executive, even after the sale; he gave up the job in 2011. He remains one of the overseers of the family’s investments. Today, thanks in part to his twenty-five years with the Mart, he is worth at least $50 million. When Christopher ran unsuccessfully in the Illinois gubernatorial primary in 2018, he would not reveal his net worth.
As for the fourth generation—the children of the third—most are also quite wealthy, again from the Merchandise Mart sale. For instance, Congressman Joe Kennedy III—son of Joe II—has an estate valued at at least $40 million; he’s by far one of the richest of all congressmen. Even Conor Kennedy—Bobby Kennedy Jr.’s son—is worth at least $10 million, and he hasn’t done a thing to earn it other than to just hire the best accountants to invest what has trickled down to him from the Chicago sale.
Of course, John and Caroline did well when Jackie died and would never have to worry about money. Still, Caroline, like all her cousins, profited from the 1998 sale. Today her proceeds from the sale—including what was invested for her and not just what she received in liquidity—combined with what she already had and invested from her mom (and then, later, from her brother) makes her, by far, the wealthiest Kennedy of her third generation. In 2018, her wealth was estimated at about $250 million.
Once, John Perry Barlow asked John about the big 1998 money deal, which John had begun to refer to as “the Big Chicago Fire Sale.” Barlow said, “That’s gotta be a lot of money for you, John.” John responded, “Well, you know, I don’t necessarily worry about money,” to which Barlow quipped, “Spoken like a man with a lot of money.” John smiled and said, “Yeah, well, you got me there.”