Sopranos "Chasing It" 6.16

A major point in this episode was the unwillingness of Tony's circle to tell him to stop the excessive gambling. Sil thinks every bet is a great idea. Christopher chastises Bobby for not being enthusiastic about Tony's horse bet. Adding to Tony's growing isolation is his falling out with Hesh, fight with Carmela, the ultimatum from Melphi, following in previous episodes the fight with Bobby, the estrangement of Christopher, and the near murder of Paulie. He also insults Carlo in a portentous way, since Carlo immediately murdered the last mob guy who told him he "sucks cock"

The sudden enthusiasm for gambling could be the need for a thrill of winning, an escape from a troubled business situation, or the assurance that his luck was still holding out.

Tony explains "chasing it" as about to win something and just as it gets within his grasp "it all falls apart" Perhaps "chasing it" also refers to Tony's attempts to escape his life, or at AJ's apparent failure at going legit.

The whole episode contained things that are broken and showed that you just can't put them back together. There's Sil, trying to repair a vase -- and then later Tony comes in and breaks up the whole room (though not the vase) ... There's Carmela smashing a vase against a wall when her marriage that she tried to patch up is falling apart anyway ... there's Vito, Jr. trying to destroy a tombstone, kicking against the father's name on it, then knocking over the angel on top...