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You are just too stupid to see the obvious Sopranos references. The Jew friend is obviously Hesh and the debt is the vig that was only paid off after his moolinian goomad had died. OP is some sort of train model master Tony, he takes insurance on all of his major business investments, but circumstances beyond his control break the various systems (or toy trains) that he owns. Vito, Richie Aprille, Ralph Cifferetto, Tony Blundetto, Chris Moltasanti and even his own son end up failing OP toy train tony.
The religious conatations are quite striking, the Catholic representation of Jesus and the stark contrast between his Jesus killing friend's stinginess often relates to how toy train Tony had behaved throughout his life.
OP is just operating on a troll level that is above the average .gs user, only a few enlightened understand the tragedy he is enacting through this humourous train thread. Perhaps you should just imagine an Italian mob version of Thomas the Tank engine and his mates.