Andrew Giuliani is only two years older than I am but he looks like he could be my uncle. Perhaps this isn’t his fault, perhaps it’s a reverse Dorian Grey situation. The portrait in the attic wants to be governor of New York, a possibility that will almost certainly not come to pass. I say this for two reasons. The first is that Giuliani is an uninspiring figure, all suit and chin. The second is that nobody knows him. They know the name, they know his father, but they don’t know him. “I’m the only candidate who’s spent parts of five different decades of my life in politics or public service,” he said at his campaign launch, a fascinating claim for a 35-year-old to make. “I think the name Giuliani evokes a reaction in most people, too,” he recently told New York. Alas for the younger Giuliani, people might not care as much as he hopes.
A family name can only go so far, former congressman Joe Kennedy warned him. “If you’re doing this because you think your last name can carry you to victory, if you’re doing this because you think it’s going to be all fun and games and people are going to come to you and cheer you on, you’ve got something else coming to you,” he told CNN’s Jim Acosta. Kennedy knows whereof he speaks, having lost his challenge to Senator Ed Markey in the Democratic primary for Markey’s seat last year. Kennedy, though, had at least served in Congress; Giuliani can boast no such experience. He is merely a son, a connection that brought him into Donald Trump’s White House and which now, he hopes, can deliver him office on his own.
In such a thoroughly Democratic state, any Republican candidate for governor faces a difficult task. Giuliani is even less equipped than most. Behind the strange mathematics of his résumé, there only lurks a void. Giuliani is known best as an offshoot of Rudy, a political late-bloomer who shows no special promise. Giuliani is a talented golfer, and there, his gifts end. For all his boasting, his time in politics really began with Trump, in 2017, as his father wormed into the president’s inner circles. Andrew Giuliani is a failson, and there will be more like him.
The failson is not a new phenomenon. Rich and successful people have produced feckless offspring for eons. Historical precedent notwithstanding, the Giuliani campaign reeks of present-day ills and his run for office prefigures others of its type. Out of Donald Trump’s brood, at least one or two seem certain to bid for power of their own. Don Jr. embodies the failson archetype with uncanny precision. Desperate for his father’s approval, Don Jr. attempts to fill the hole in his heart with the support of his father’s base. He’s taken to posting videos on Rumble, an alternative social-media platform funded by the likes of Peter Thiel. Here, Don Jr. bellows into nothingness, trying to make his thoughtless father proud.
The youngest scion of the Bozell family, all famed conservatives, faces federal charges for participating in the January 6 Capitol siege. Where his father founded the Media Research Center, and his grandfather was for a time the writing partner of William F. Buckley, Brent the IV worked out his antagonisms in a less intellectual manner. He exercised brute force, and even in this he was unable to secure his goal: He did not keep the Capitol, and Donald Trump is no longer president. Gender-swap the failson, and either Ivanka or Tiffany could fill the role. Dinesh D’Souza’s daughter, Danielle, is following her father on the far-right speaking circuit, bereft of even the fleeting intellectual cachet her father once enjoyed. The D’Souzas will speak at a June 12 rally in northern Wisconsin, organized by MyPillow founder and Trump loyalist Mike Lindell.
The partisan affiliations of a prominent family matter less than its wealth; the trope is about status and power. The private-school circuit feeds off fear of the failson, as families of means spend richly to ward off the vampiric nightmare: a leech on the family fortune. Send him to the right schools, where he becomes someone else’s responsibility, make sure he goes to the right college, and he’ll hold his own. The tides of wealth can overpower such thinking; nannies and educators vie for a young soul against a level of entitlement that forms its own impermeable shield. What you get, often, are Giulianis, legions of them, all with great educations and interesting family names and nothing that resembles a heart or a brain. Sometimes they go into finance. Sometimes they become lawyers, or dabble in the arts. And sometimes, they try to run for office.
This is not an unusual occupation for the failson. Look at Andrew Cuomo. The failson is doomed to either seethe in the shadow of a more successful parent, or to try to replicate that success for himself. He is equally doomed to squander his endless chances. He is the symptom of a moribund ruling class, the sign of an age in decline. Andrew Giuliani won’t even achieve Cuomo’s high status. He will never be the governor of New York, but he’ll raise some money along with his profile and earn some plum speaking gigs, maybe even bump himself from his father’s current level of hell into something a little more prominent. The failson is a martyr to himself, and to his own self-delusions, which are those of his class.
America’s wealthy families have all they could ever dream. The Trump years enriched them; Democrats aren’t powerful enough, or willing enough, to truly dislodge them. What have they wrought, with all that power? A weary country, broken by the failures of its own mythology. There is no meritocracy, no reliable ladder to the top. There are failsons, and then there’s everyone else.
