A mathematician and a computer are playing a game: First, the mathematician chooses an integer from the range $2,...,1000$. Then, the computer chooses an integer uniformly at random from the same range. If the numbers chosen share a prime factor, the larger number wins. If they do not, the smaller number wins. (If the two numbers are the same, the game is a draw.)
Which number should the mathematician choose in order to maximize his chances of winning?










First consider choosing a prime $p$ in the range $[2,N]$. You lose only if the computer chooses a multiple of $p$ or a number smaller than $p$, which occurs with probability $$ \frac{(\lfloor{N/p}\rfloor-1)+(p-2)}{N-1}=\frac{\lfloor{p+N/p}\rfloor-3}{N-1}. $$ The term inside the floor function has derivative $$ 1-\frac{N}{p^2}, $$ so it increases for $p\le \sqrt{N}$ and decreases thereafter. The floor function does not change this behavior. So the best prime to choose is always one of the two closest primes to $\sqrt{N}$ (the one on its left and one its right, unless $N$ is the square of a prime). Your chance of losing with this strategy will be $\sim 2/\sqrt{N}$.
On the other hand, consider choosing a composite $q$ whose prime factors are $$p_1 \le p_2 \le \ldots \le p_k.$$ Then the computer certainly wins if it chooses a prime number less than $q$ (other than any of the $p$'s); there are about $q / \log q$ of these by the prime number theorem. It also wins if it chooses a multiple of $p_1$ larger than $q$; there are about $(N-q)/p_1$ of these. Since $p_1 \le \sqrt{q}$ (because $q$ is composite), the computer's chance of winning here is at least about $$ \frac{q}{N\log q}+\frac{N-q}{N\sqrt{q}}. $$ The first term increases with $q$, and the second term decreases. The second term is larger than $(1/3)/\sqrt{N}$ until $q \ge (19-\sqrt{37})N/18 \approx 0.72 N$, at which point the first is already $0.72 / \log{N}$, which is itself larger than $(5/3)/\sqrt{N}$ as long as $N > 124$. So the sum of these terms will always be larger than $2/\sqrt{N}$ for $N > 124$ or so, meaning that the computer has a better chance of winning than if you'd chosen the best prime.
This rough calculation shows that choosing the prime closest to $\sqrt{N}$ is the best strategy for sufficiently large $N$, where "sufficiently large" means larger than about $100$. (Other answers have listed the exceptions, the largest of which appears to be $N=30$, consistent with this calculation.)