When you speak of something “going very slowly” through the Earth’s atmosphere, you’re talking about something with a more or less synchronized speed relative to Earth. So objects that take off from Earth, don’t go through the atmosphere into orbit, and then land again, would qualify. This is up to and including ICBMs (Inter Continental Ballistic Missiles, for those who grew up after the 60s and didn’t hear much about those.)
Most things entering the Earth’s atmosphere from orbit or from outer space don’t so qualify.
Keep in mind that the Earth moves in a giant circle around the Sun. That circle has a radius of 93 million miles (give or take), so the circumference of the circle is over half a billion miles (measured in Earth units). This means that each day the Earth travels 1,600,000 miles along that circle, or approximately 66,700 miles per hour. (Again, to keep this in comprehensible Earth units.)
So if your “little army man with a big parachute” weren’t already “inside” Earth’s atmosphere, but was either in another orbit of its own or somehow “stationary” in space, but in Earth’s path, then what would happen would be a literal “collision” of the orbits. And in that case, that “little army man with the big parachute” would likely not survive the “collision”. Since its speed relative to Earth’s at the time of the “collision” could be at a huge speed differential, then it would probably burn up, just like any meteorite.
What would more than likely happen is that as it approached Earth’s atmosphere it would be affected by and enveloped within Earth’s gravitational field and spun into orbit around this planet on its own, until its orbital speed decreased over time and it dropped into the thinnest atmosphere, slowed down more, and then began free fall.
Don’t forget that at the outer edges of Earth’s atmosphere there is no “air” to make a parachute very useful… just enough to create the friction that causes the burn. In any case, if it entered Earth’s orbit from “outside” the atmosphere, whether from a decaying orbit of its own or as some kind of projectile or “collision”, then it would burn up unless very special measures were taken to protect it.
@DrMC, your postulated 50k mph speeds aren’t so unrealistic after all.