There was a weird and grim story in the New York Times on Sunday. The story starts with two “old money” brothers: George Seymour Beckwith Gilbert (born 1942) and Thomas Gilbert (born circa 1944). Their father ran a company that made textile machinery, back when America still had a textiles industry. The parents sent the boys to Philips Andover and then to Princeton (Beckwith ’63, Tom ’66). Both went on to get MBAs (Beckwith from NYU, Tom from Harvard). Both went into finance. Thereafter their career tracks diverged. The older brother worked for firms that bought and turned-around poorly performing companies. There were a lot of these in the America of the Seventies and Eighties. Eventually he founded Field Point Capital Management Company. Later, he got interested in science and medicine. This led him to get an MS in Immunology from Rockefeller University (2006). He’s on a bunch of boards, corporate and academic. You could read this as an example of how people get to the top of American society and how subsequent generations stay there: a combination of brains, hard work, and the opportunities that come from social networks.
Tom Gilbert’s career seems to have run down a different course. People from Princeton remember him as affable and athletic, rather than as highly intelligent. He worked in a bunch of jobs at Wall Street, including a seven-year stint at Loeb Partners that ended in 1991. In 1998 he founded Knowledge Delivery Systems (KDS) to provide on-line education materials. In 2010 he co-founded Syzygy Therapeutics LLC. He stuck with that for a little over a year, and then founded his own private equity firm, Wainscott Capital Partners LLC, in April 2011. He was sixty-seven years old and starting a new venture.
Should we see this new venture as admirably lively or as desperate? Possibly the latter. Tom Gilbert, Sr. left an estate worth $1.6 million. Oddly, and my saying this will infuriate most people, that isn’t a lot of money. About a third of his assets were his stake in his new fund. He had a house (not a “mansion”) in the Hamptons; he belonged to a couple of clubs (River in New York, Maidstone in East Hamptons); he was selling the house in the Hamptons; he and his wife had given up a brownstone on the Upper East Side for a smaller apartment on Beekman Place. He put in twelve-hour days at his new business and never took vacation. You could read this as an example of how people get to the top of American society and how subsequent generations struggle desperately to stay there: more social than smart; hard work; and the lack of social networks as the economy goes through revolutionary changes.
Beneath the surface of this little bit of social history a la Louis Auchincloss is a sadder tale that also speaks to other contemporary concerns. Tom Gilbert was (apparently) a loving, doting father who had a troubled child. Tom Gilbert, Jr. (born 1984) had followed in his father’s footsteps: he graduated from Deerfield and then from Princeton, with a degree in economics. He loved sports and had a wide circle of friends. However, something was wrong. He graduated from Princeton in 2009, when he was twenty-five. Something slowed him down. He never managed to start a career. Instead, he lived off his father: the $2,400 monthly rent on an apartment and an allowance of $600 a week. Meanwhile, his friends from Deerfield and Princeton pressed on with the usual careers in business, law, and government. He went to parties, saw them, and what could he say when they asked what he was doing?
About a year ago, perhaps in late 2013, things started to get dramatically worse for the Gilberts. Tom, Jr. got barred from the Maidstone Club for giving one of the employees a bad time. He had a fight with a friend (possibly over a woman); the friend got a restraining order; Tom Jr., violated the restraining order and got arrested; somebody burned down the family summer home of the friend; the police wanted to talk to Tom Jr. about this episode, but never charged anyone with setting the fire. More and more friends stopped seeing him. Tom Jr. got a gun and started spending time at a range. Some of Tom Jr.’s friends told Tom Sr. that they were worried about his son. Undoubtedly, Tom Sr. was worried as well. He had paid for a lawyer to resolve some “minor matter.” He may have persuaded his son to get medical help and paid for that. Tom Jr. doesn’t seem to have appreciated the help. He became critical, even mocking, of his father.
The two strands of Tom Gilbert Sr.’s life came together in early January 2015. He was making sacrifices to get his fund up and running by downsizing his own life-style. Truth be told, he wasn’t getting any younger and there was no guarantee that he would be able to build his fund into a real fortune. He probably wasn’t going to be able to leave a huge inheritance to his family. Tom Jr. may have seemed stuck in a life going nowhere and in need of some kind of help. Either because the financial pressures he faced were becoming grave or because he hoped to nudge his son toward becoming self-sustaining, Tom Sr. told his son that he would have to reduce his allowance. On Sunday, 4 January 2015, Tom Sr. was shot once in the head in his apartment. Police arrested Tom Jr. later that day.
Some in the media want to make the story about the harmful effects of “privilege.” That isn’t what it’s about. Instead, the story is about two things. One is that inherited “privilege” is nowhere near as reliable as it once may have been. The differential fortunes of the two older Gilbert brothers illustrate that point. The structure of the American economy has been changing fast. The decline of old industries has wreaked havoc with blue-collar and middle class incomes. Did it do the same with upper-class inheritances, forcing a whole generation to seek opportunities to restore or shore-up their assets? The composition of the American financial elite also appears to be changing in response to the rise of new industries. Adapt or disappear.
A second thing is that a troubled adult is hard for anyone to assess, help, or control. It’s hard to tell how far a person will fall. It’s difficult to get anyone institutionalized after they hit fourteen unless they do something that makes people say that they should have been institutionalized before they did it. It’s easy to say that someone needs help, but harder to find help that works. It’s easy for people to get their hands on firearms, even when there is a restraining order against them for one thing and they’re suspects in a crime for something else.
Of the two themes, the second seems far the more important, the outcome the most tragic. Parents of all social classes and races have struggled with troubled children. Sometimes things work out. Life for everyone gets progressively better. Sometimes they don’t and there flows a river of tears.
 Landon Thomas, Jr., “The Price of Privilege,” NYT, 18 January 2015.
 Are they related to the Seymour Parker Gilbert who was a New York investment banker and later was Agent-General for Reparations in the Twenties?
 If you look at the current leadership team at KDS you can’t help but get the feeling that they are not “old money” or “old school.” BAs from Tufts, Yeshiva, Wake Forest, Gettysburg, UCLA, Kenyon, George Washington, North Texas State, and Howard. Blacks, women, and Jews. http://www1.kdsi.org/about-kds/kds-team.htm
 Well, it isn’t a lot of money for a 70 year-old guy who came from money, got a first-rate education, and spent his working life on Wall Street.
 So he’s costing the father $60K a year. Do all rich families subsidize their children in this fashion while the kids get their feet or is this an exception to the rule?
 The incident may have been really egregious or not the first time if it got him banned.
 Glock 22: .40-cal. pistol favored by big-city police departments and the DEA. Ugly piece of work.