"It wouldve been me crying the blues"

Rewatching season two at the moment and had a question pertaining to the episode "Bust out." When Tony finds Davey in a tent in his store that night they have a brief conversation about the executive game. Scattino is pretty depressed and asks Tony, "Why'd you let me play?" Tony says something like, "Well I knew if you couldnt pay, you had this store here." The Scattino starts crying or something and Tony says, "Hey, you couldve won. Then it wouldve been me crying the blues."

I'm not sure about this comment. If Scattino wouldve won, he wouldve just paid Tony back the money he borrowed right away from his winnings. Tony wouldnt have gained anything, but he wouldnt have lost anything either. He wouldnt have gotten to bust out the store, but I dont think he really ever wanted it to come to that in the first place. Plus, even though they got a lot of of the store, he was still out 45K. He knew that was the last resort if Scattino became massively indebted to him. He told him twice that this wasnt the game for him and he shouldnt play.

So why would Tony have been "crying the blues"if Davey had won big that night?

Perhaps Tony was trying to (patronisingly) cheer Davy up; or even rub salt in the wounds by having Scatino feel he was somewhere close to winning.

Mick

If he had won big that night then Tony would be out a lot of money.

DS

I dont understand why Tony would have been out any money. Scatino wouldve paid him back the money he initially borrowed right away if he'd won.

It was an all-night game, Scatino had endless scope to win back what he borrowed, and lots more. Remember, he was playing against gangsters with loads of cash.