I do not want to sound like dumb ass and spoil the fun but the "correct answer" posted today by Richard O' Brien is
wrong. It violates Newton physics principles.
Here is why:
Answer : The "dead calm" sailor. The water is carrying the vessel at 5 mph, creating a 5mph wind, filling his sails a bit, and allowing him to take advantage of the airfoil shape, thus increasing his hull speed just slightly more than the existing 5 mph.
The "dead calm" sailor boat is not encased in concrete but floats in water. The apparent wind will push him back "against" the current and thus slowing him down over ground. Is is impossible to say by how much. (It depends on size and shape of sails and rig and size and shape of part of the hull above waterline and size and shape of bottom of the hull submerged in water - about 800 times denser then air - and many, many other factors) If he set sails and try to tack he will recoup some of the lost speed but it is impossible regain 100 percent as some of available energy will inevitably be conveterted to heat due to friction. Also the boat will be making leeway from the finish line. According to puzzle his
only source of energy is kinetic energy of current. This is may be tricky but what energy you take from wind to propel the boat you are taking it from current too. You move over the water but entire body of water is moving slower over ground from your perspective. His overall progrees to finish will be less. Some of the available energy will be converted in the form of heat which is not usefull for moving toward finish.
The total amount of energy must be preserved. It is unquestionable law of physics. It can not be broken.
It is all a matter of available energy.
It does not matter how efficient sailing of the first guy will be.
Other sailor has
additional source of energy in form of kinetic energy of the wind on top of energy of current. The wind flowing with the direction of current will nulify effects of air drag of sail rig and portion of hull above water to his advantage over "dead calm" sailor. He do not have to to anything to counter any drag as the additional wind will help him win this race.