Event Year: 1999

The relationship between Christopher and Paulie’s falters, while A.J. grows depressed over his break-up with Blanca.

Maria Spatafore requests help from Tony for Vito, Jr.; Tony’s bad luck puts a rift between he and Hesh; A.J. makes a major choice regarding his future

When Tony’s first hit is about to be unearthed, he and Paulie flee to Florida, where Tony contemplates their friendship; Junior organizes a poker game at the institution; the New York power struggle continues

Christopher’s Cleaver premieres, showing Tony how he feels about him; Johnny Sack faces a health crisis; Phil Leotardo resents his family, and himself, for being weak and downtrodden; Silvio gets caught up in New York’s power vacuum

Bobby and Janice host a wild 47th birthday bash for Tony at their Adirondacks vacation home. Tony’s actions following Johnny Sack’s arrest come back to haunt him.

Phil Leotardo seeks to continue a cycle of retaliation between the New York and Jersey families. Christopher wrestles with his addictions. Tony decides keeping Carmela occupied with the spec house is for the best. A.J. gets a new girlfriend.

Tony seeks to find a peace with the Leotardo crew while dealing with rumors a member of his own crew may have flipped. A.J. makes a decision regarding his future and Junior’s slide into dementia continues.

The spectre of disloyalty among the crew hangs over Tony as Phil Leotardo decides how to handle recent issues with the Soprano crime family; a hit gone wrong comes at a huge cost; A.J.’s conquering of his depression is challenged

Tony attempts to repair the rift between New Jersey and New York; A.J.’s depression struggle continues; a New York associate crosses the line with Meadow

The Soprano and Lupertazzi crime families quarrel over asbestos removal; Tony deals with a problematic associate; Paulie suffers a devastating personal loss; A.J. questions his friendship with Jasons Parisi and Gervasi