Tony's biggest problem was his ego. In fairness, I feel nearly every beef could have been settled in Jersey's favor for the sake of the show, however, rarely was for the sake of Tony's inability to reign people in or reach realistic common ground.

I've never quite agreed with the idea that Tony was a pragmatist. Johnny Sac as indicated was always a pragmatic strategist before he became Boss. Tony is labelled similarly by the show, yet I've never felt the same about his decisions. Some were very smooth, but many were marred by too much emotional judgment.

*He chiseled Junior's pockets until the day he died. Had he continued to placate his uncle, the murder attempts would not have escalated.

*He allowed emotion to cloud judgement with Ralph. He turned the North Jersey mafia into a popularity contest and killed his best earner for being generally creepy and off putting. Surely there are dozens if not hundreds of much less reputable types in real life that are left to earn, and Ralph was the literal TOP earner. There's no plausible justification for that, point blank.

*He emasculated Richie. I'm admittedly not a fan of Richie as a character, however I feel he could have served much more of a purpose then single season guest antagonist. In reality, Tony made no legitimate attempt to reign Richie in, and did little to make him feel welcomed back into the fold. Richie didn't deserve much IMO, yet I still feel he deserved more than he camp back to and had he been met with more acceptance upon arrival I feel he would not have challenged for authority. However, Richie was an asshole, yet Tony still mishandled it.

*Not killing Phil after the botched attempt spiraled out of control. That mistake can't happen. In real life, you have shooters, back up shooters. This was so poorly mismanaged in an attempt to keep everyone away from it, they completely fumbled the hit that helped ignite the war.

*Killing Rusty was a HUGE mistake. Tony did so little to curry favor with NY because he never felt he needed to. Had he appeased or appealed to Senior Lupertazzi members earlier, Phil would never have had the opportunity to amass a power base.

*Waiting so long to bring Bobby into the mix was a grave mistake as well. While they lacked for depth in their crew for no reason other than weight Bobby was made to be lesser than. He was continued to be tormented and under-appreciated while dating Janice. We all observe during the series how capable Bobby is in most situations, waiting until the series was nearly over to have fully placed him in a leadership role was a mistake on Tony's part. Especially since they lacked for leadership and vocal leadership at that.

*Killing Christopher was likely his biggest mistake of them all. Say what you will about the drug issue but Christopher is the only one left at the end of the show had Tony not killed him. One would imagine he would have been active during the war with NY. It's hard to thing Carlo could have indicated Chrissy in the information he has informed considering the separation between Tony and Chris in business ventures to maximize total net gain while keeping each other's exposure minimal as possible. If Chris doesn't die in the war w/ NY, (IMO he's the most important guy to protect on the Jersey faction in that war due to youth/earning capability) he is likely running the show not long after the war. Bobby dead, Sil a vegetable, Carlo informing, Tony dead or indicted, Patsy either jumped ship NY or indicted. Who is left in that scenario to lead but a few key guys. Chrissy, Paulie, Benny. Food for thought...