You’d like to think that the President of the United States is known for making good decisions. That’s pretty much out the window at this point, but once upon a time, it was a hope. That decision-making prowess, though, was in terms of domestic and foreign policy, not necessarily their personal life. Specifically, there have been plenty of presidents who have made some highly doctor-unrecommended decisions in terms of their personal health. I don’t know if any of them were knocking back two hamburgers and double fried fish sandwiches every day, but they definitely would have earned a “hmm” at their annual checkup. 

5 James Madison

If you’re considered sickly in the 1700s, that means your skin was probably falling off on the regular. Madison was so famously unwell that it was a central character trait when portrayed in Hamilton. In reality, a simple cough would have been a good day for him. He had seizures, depression and contracted malaria far more times than the recommended “zero.” He’s also referenced as being a hypochondriac, which feels a little mean given how messed-up he actually was most of the time. Going to the doctor every day probably would have been a perfectly reasonable activity for him. 

He apparently was stricken repeatedly by something called “bilious fever” as well, which I assume is exactly as disgusting as it sounds.

4 Dwight D. Eisenhower

Unlike Madison, Eisenhower’s health problems weren’t nearly as unlucky as they were exacerbated by stubbornness. He racked up a couple of serious medical events over his lifetime, including both a heart attack and a stroke. Neither, apparently, was enough to break his deep love for smoking. As if he needed more reason to possibly adjust his diet, Eisenhower also suffered from a particularly nasty digestive disease known as Crohn’s, which is sort of like if irritable bowel syndrome could send you to the hospital. Despite the pain it caused, he continued to eat gut-shaking dinners like pig knuckles and sauerkraut. 

He would eventually die, tragically but not surprisingly, from congestive heart failure.

3 William Taft

Taft, a famously corpulent commander-in-chief, reached a peak weight of 335 pounds, enough to raise eyebrows anywhere outside of Dallas, Texas, and something that’s pretty easy to achieve when your breakfast includes, but is not made up entirely of, a 12-ounce steak. In addition to exactly all the sort of problems you’d expect his obesity to cause, he was also famous for constantly falling asleep, something that doctors now assume was because of obstructive sleep apnea connected to his weight.

2 Grover Cleveland

Grover Cleveland probably wasn’t hitting all of a physician’s preferred marks throughout his life, given his weight, his love of smoking and his hate of exercise. The most serious health problem that sets him apart from other presidents, however, was a nasty cancer that developed during his second term. His doctors noticed the tumor growing in the roof of his mouth, which, if you were spinning a carnival wheel of cancer locations, would probably be one of the ones with a skull on it. 

He didn’t want to send the nation into a panicked tailspin, so he had a secret surgery on a boat, where doctors went in through his mouth and removed the tumor, a bunch of teeth and a good portion of his soft palate. They had to do it all with the directive that he not be forced to shave his mustache, so as to keep the public unaware.

1 John F. Kennedy

You wouldn’t think Kennedy would make this list, given his relative youth compared to most presidents. Yet, JFK was riddled with health issues. He was such a frequently sick child that the other Kennedys made jokes about it, saying that if a mosquito bit him, the mosquito would die. He dropped out of two different colleges because of illness, and had to have his father overrule a failed physical to get into the Navy. He also had an adrenal condition known as Addison’s disease that causes fatigue, fainting and pain, and was on a 12-drug medication regimen while in the White House. 

But damn, he looked good on a sailboat.