When you first start off, bet on Winner of Game and Leader At Half. Play up until you get to the Dome level. Once you become familiar with the game or already know it, you should have close to $50,000. Easy money winners are, 10 Grand on Winner of Game, Leader At Half, Most FGs, Most 3's, and Most Steals. You have a better chance of stealing and making threes when you become on Fire.
Play a one on one game (controller one vs. controller two). Bet money on the game, keep playing the game over and over, and watch your money grow.
Get at least $30,000 then play a one on one game. Go to bet. Bet on most 3's, winner, and dunks. You will have a better chance at winning. If not, restart the game and it will be as if you never made the bet.
Create a player that is horrible. Start a Lord Of The Courts game and get your team set. Then, go back out and play a Half Court Game, 1 vs. 1. Select your best player and play against the bad player you created. Keep betting on things that you are sure that you can win. The game only allows a $10,000 maximum on each separate thing you can bet on. Keep betting and playing that same person repeatedly. When you are comfortable, go back to your Lord Of The Courts game and you will have the money.
Note: This trick requires two controllers. Go to the game modes screen and set up a game against yourself; player one on one team and player two on the other team. Next, go to Cash Checking/Bookie and play. Bet on the winner, most 2 pointers, etc. You will easily win the game and double your money.
Note: This trick requires two controllers. Go into half court mode and select one-on-one. Bet a lot of money then have player two miss frequently and travel. When it is player one's turn, play well.