Season 2: Episode 46: Jimmy's Got Balls
While drawing up their will, Greg and Kim have a difference of opinion on who should get custody of Sam in the event of their deaths. Kim wants Jimmy and Christine to have him. Though Greg thinks Jimmy is too irresponsible, he ends up deferring to Kim's wishes. When they tell Jimmy and Christine about it, Jimmy wonders how they expect a mooch to raise three kids. He learns that Greg's life insurance policy will handle that. But since Greg only agreed to trust him with his son and not his money, the funds were entrusted to Greg's sister instead. Jimmy is insulted that Greg feels he's too incompetent to manage his finances. Against Greg's wishes, Kim decides to give Jimmy $1500 of their tax refund to invest to prove his mettle. After a failed attempt at playing the stock market, Jimmy takes the entire $1500, plunks it down on a wet suit and scuba diving lessons, and starts up a golf ball retrieval service, fetching balls that golfers hit into the lake then selling them for profit. Greg bumps into Jimmy, Dominic and Logan on the golf course and is disgusted when he sees what was done with his money. Factoring in all the balls he retrieved on the first day, Jimmy tells him that, at this rate, he'll turn a profit in three months. But on the second day, Jimmy retrieves so little that he realizes his golf ball well ran dry. In desperation, he enlists Dominic to help lure the balls away from the golfers. When that too doesn't turn a profit, and he then finds out that there aren't any more balls in the lake because the golfers who use the course are professionals, Jimmy is forced to take a bath and admit that Greg was right about him. However, when Greg hears that the reason Jimmy chose this particular bad investment was so he could spend time with Dominic and Logan, he sees that even though Jimmy was careless with money, he won't be careless with Sam.