Interesting topic.
My opinion may surprise a few people.
Assuming you DO have access to additional money (in other words, you can raise a stake for next season -- be it football or baseball, or whatever), you should be MORE INCLINED to make a bet of this kind the smaller your bankroll gets in proportio to your initial stake. If indeed, your GOAL was to make 2x of your initial bankroll (over the course of the season), and you have now lost 50 percent of the BR to date, it is not a bad play to shoot the entire BR on a single game. This assumes, of course, that you have done your research and there are VERY compelling reasons for making the play (i.e., a bet on the Dodgers). This also assumes you are a man of your word and will not make a bet again on baseball this season, if you lose. If you continue betting after you lose, this would be absolutely suicidal.
Conversely, the LARGER your BR becomes the LESS LIKELY you should be willing to make sizable wagers, or a wager of this kind. If you start with $10K and three months later you are at $15K, it would be preposterous to bet the entire BR on a single game. However, if you have lost half of the BR and you are at $5K, it is a justifyable action to bet very large on a single game -- assuming your goal is to make $20K. If your BR is only $2K or $3K, it's almost mandatory that you do this (bet it all on one game) -- that is if you still want to meet your goal.
This topic is analogous to the concepts of money management adressed by the world's foremost gambling authority, David Sklansky (who resently read me the riot act for a column I wrote about hourly and annual earning expectation in poker). David suggested that the closer you are to bankruptcy, the MORE RISK you can afford to take. For example, a poker player that has only a $500 BR would be advised to go ahead an sit in a $10-20 game (not a $2-4 game), because that way he can quickly get back to the level of betting that will enable him to reach his initial financial goals.
Similarly, if you are a sports bettor and you started with X dollars, then lose half the money -- assuming you are comfortable with taking a few months off if you lose, it is perfectly defensible to shoot the entire BR on a solid play which, if you win, will put you in a much better position to reach whatever esoteric numbers you had in mind.
HOWEVER, THIS IS TOTALLY PREDICATED ON HAVING A JOB OR OTHER MEANS TO GET MONEY, IF YOU LOSE. IF YOU ARE GAMBLING FOR A LIVING AND HAVE NO FINANCIAL MEANS, YOU CANNOT AFFORD TO MAKE THIS RISK.
-- Nolan Dalla
[This message has been edited by Nolan Dalla (edited 06-11-2001).]