When Artie loses the 50 g's Tony lends him and Tony pretty much gives him a pass. Losing that amount of money in real life would have at least cost Artie part of his restaurant if not his life. I know they were friends but Tony was also friends with Davey Scatino and that didn't stop him from busting out his sporting goods store. Also this is my first post here on the site but have been following it for years.
Tony didn't lose the $50k though, he got Furio to collect it from the French guy in exchange for Artie clearing his tab at his restaurant which was a about $3-5k.
Plus, Tony was going through a dark time then, dealing with Gloria's suicide. Remember when he says to Janice, "what am I, a toxic person?". He was heavily depressed, doubling down on the prozac and drinking Artie's new line of vodka all day, having weird dreams about Gloria. He was carrying the world on his shoulders and blaming himself for everything. So, Artie couldnt' have picked a better time to do this. The more benevolent Tony is more afraid of being a "toxic person" than he is showing weakness by letting Artie get away with losing 50k of his. Furio probably got most of it back, along with some of Jean-Philippe's belongings for score, but Tony has better things for Furio to do.
When Dave Scatino got in deep with the crew Tony was riding high as a newly minted boss. And, of course, in the same episode, "Bust Out", he's also facing an indictment over Bevelaqua, but that was nothing compared to the rock bottom he'd hit in "Everybody Hurts". Tony was a different person by then. I also think Tony regretted busting out Scatino. Those few updates Meadow gave him through the years on how fractured the Scatino family had become seemed to hit him in the gut. Tony was not boss material. He was a soldier by nature.
