At any given moment in the race, it might look like the hare is winning.

But also at any given moment, they are more likely to die (or, less morbidly, to go to sleep and miss the rest of the race).

How far ahead they are is more obvious and visible than how likely they are to die.

That asymmetry of optics makes it look like they are winning when actually they might be more likely to lose.

The tortoise stays inside the adjacent possible.

They are more likely to win not because they are faster at any point, but because they are more likely to survive to the end.