As you might expect, New York and California have the highest number of total Cartoon Caption Contest wins with 87 and 76, respectively. But they also have the most losing entries.
This map shows that Alaska is actually the most successful state in terms of wins per ten thousand submissions! Though Alaska has only won the contest twice, the fact that it had a mere 2,102 documented contest entries renders its rate of approximately 9.5 wins per ten thousand submissions the highest in the country. Mississippi, another state not commonly associated with the New Yorker crowd, comes in at a close second, with 8.14 wins per ten thousand submissions.