Sentence 1: Jeff needed a big amount of money. 
 Sentence 3: Jeff decided he had to take extreme gamble 
 Sentence 4:  Jeff bet all of his life savings on the basketball game 
 Sentence 5:  Jeff won and covered the spread to win it all 
 Option 1: He had made some bad bets and was down big. 
 Option 2: He had made some bad bets and was out of money completely.