Paul Pierce wants to retire a Boston Celtic. The Celtics want Paul Pierce to retire a Boston Celtic. So what's the hitch? As usual, it comes down to money. And in this particular case, it comes down to money and years.
Paul and his agent are looking for financial security. That sounds funny when talking about someone that's earned well over $100 million over his career, but only a special breed of person can leave millions of dollars on the table (yeah, Richard Jefferson is an example). Pierce needs only look as far as his buddy Antoine Walker to see how quickly $100M can disappear when not managed properly.
In the other corner sits Danny Ainge and the ownership group. Nobody is going to be crying poor on their side either, but for them it boils down to cap flexibility in future years. They want to bring the gang back together for another run but not at the expense of the next 3 years of Rondo's prime.
I think both sides can come up with an annual dollar figure that makes sense for both parties, so it really boils down to the years. The Celtics will want to limit the deal to 2 years so it lines up with Kevin Garnett's deal. Pierce will likely want 3 to 4 years. Who will blink?
It seems to me that both sides have limited leverage. Pierce can threaten to go elsewhere but he's already stated time and time again that his legacy is important to him and he'd like to finish up with the team that drafted him. Could he get more money from another team? Maybe. For the most part it would seem that Pierce is more valuable to the Celtics than he would be to any other team, but all it takes is one LeBron-gilted owner to offer the moon. Some are speculating that team could be the Clippers. Los Angeles would be appealing because it is Paul's home town, but still, ...we're talking the Clippers here.
The Celtics could threaten to move on without him, but how are you going to sell that to a coach that just agreed to put his family aside for another year? How are you going to sell that to a fanbase that has tasted greatness and isn't quite ready to return to lotteryland just yet? Besides, what's the plan B? Renounce all the free agents' rights and sign one B-level free agent that you'll have to overpay? You'd also have to fill out the roster with minimum salary guys and undrafted rookies.
So we are back to square one. Paul Pierce and the Celtics need each other, so something is going to get done. It is just a matter of time (and money and years). For point of reference, Manu Ginobili signed a 3 year extension for $39M. When all is said and done, I'd expect Pierce to get something similar.