One day when my mind was obviously a black hole utterly devoid of anything stimulating to think about, I wondered why so few presidents of the United States and aspirants for that office were sailboat owners.

I think I found a partial answer when I came across an article in an online archive with a headline that read, “Boxer calls out Fiorina as a multiple yacht owner.” 

There you have it—the stigma of yacht ownership. The word “yacht” is so heavily freighted with images of wealth, privilege and elitism, not to mention wretched excess, that no politician wants his or her name in the same sentence with it, with the notable exception of Donald Trump.

The article referred to the 2010 race for U.S. senator from California between Barbara Boxer and Carly Fiorina, who is now a candidate for president. It turns out that Boxer’s claim—I guess you could call it an accusation—was accurate. Fiorina owned two yachts, both powerboats, a 70-footer moored at Sausalito and a 56-footer kept in Washington, D.C. Oh, the shame.

Trump, also a presidential candidate, feels no shame whatsoever about his yacht ownership and has managed to turn images of wealth, privilege and elitism into political assets as markers of a successful person. This in spite of the fact that his yacht defines wretched excess. 

It’s a powerboat of course, 280 feet long, upholstered with 11,375 square feet of suede, built for the world’s biggest arms dealer, once owned by a sultan and now one of the few boats in the world named after its owner. Trump is not the least bit bashful about any of that and cheerfully claims the Trump Princess is worth as much as $200 million.

Trump is doing fine without any advice from me, but I would suggest to other presidential aspirants that if they want to own a yacht it should be a sailboat. Sailboat skippers are perceived as bold, skilled and self-reliant leaders in tune with nature and respectful of the environment, presidential qualities all. Plus, sailing offers opportunities for irresistible photographs—the resolute skipper at the helm of a sturdy vessel under sail on a whitecapped sea, a man or woman clearly capable of taking the helm of the ship of state.

Adroit imagemakers could also make the case that their sailor-candidate is well qualified to be a fiscally responsible chief executive. Anyone in the marine industry could tell them that sailors, unlike spendthrift powerboat owners, are congenitally parsimonious. No matter the size of their boat or their net worth, they are tightwads. Boatyard owners can tell stories of captains of industry who would rather try to fix their sailboat’s malfunctioning marine toilet themselves, usually with dubious results, than pay for one of the yard’s trained head experts to do the dirty work.

In spite of those political advantages, I could find only two presidents who pursued sailing. Six presidents had been officers in the Navy—Kennedy, Johnson, Nixon, Ford, Carter and Bush senior—but only John F. Kennedy and Franklin D. Roosevelt (who had served as assistant secretary of the Navy) were recreational sailors.

FDR sailed as a boy on his father’s 51-foot Half Moon. At the age of 16, he owned a 21-foot Knockabout named New Moon. He sailed on other family-owned boats when he was a presidential candidate and president. He loved sailing for its aesthetic rewards, but he loved it too for the political rewards of the sailor-president image.

“Roosevelt used his affinity for sailing to help create the image he enjoyed of himself as an imposing national captain,” historian Michael Beschloss wrote.

He needed that image. It helped maintain a vigorous facade that kept the public in the dark about the fact that he was crippled by polio and could barely walk. (Imagine getting by with that in this age when refusal to reveal a president’s cholesterol count or presence of an ingrown toenail would be considered a scandalous cover-up.)

The value of a sailorly image probably figured in Kennedy’s political calculations too, yet in the dozens of photos I found of him on sailboats you see a man who seems to be there just for the pure enjoyment of it. 

One of the photos rang a bell with me because it showed Kennedy, wearing a big smile and a blue jacket bearing the presidential seal, steering a boat I had seen on Lake Michigan as a child. It was the 62-foot Sparkman & Stephens yawl Manitou, a gorgeous vessel that sailed many times through its namesake waters—the Manitou Passage in the northern reaches of the lake—on her way to victories in the Chicago-Mackinac race.

As a senator, Kennedy admired Manitou when he saw her in the donated-boat fleet at the Naval Academy in Annapolis. After he became president he had the wooden boat, then 24 years old, fitted out as a presidential yacht.

A reference to a boat he owned as a teenager, a Star class one-design named Flash II, came across my desk earlier this year in a news release.

It announced that the boat was to be sold at auction—in Dallas, Texas, of all ironic places. The minimum opening bid was set at $100,000, but the owner predicted the boat would sell for $1 million owing to its value as Kennedy memorabilia. 

Perhaps the worth of the boat’s provenance was diminished by the fact that in 2004 it was seized by the Drug Enforcement Agency after its then-owner was convicted of marijuana trafficking. In any case, it attracted no bidders.

This may suggest that people don’t care that much about sailing as it relates to presidents. Still, there must be some American citizens like me who would like to see pictures of their president at leisure on a blue sea on a sailboat instead of on a green of yet another golf course.

Looking at the field of presidential aspirants of both parties, I don’t see a likely candidate to be a sailing president. Still, I’ll hold out hope that the next presidential yacht will have 11,000 square feet of sail instead of suede.