As a premise, I am strongly of the opinion that I feel Marcus Smart fits very solidly in a backcourt rotation with Rondo and Avery Bradley. There are probably 20 threads that have been created in the last week where this is debated -- I'd like this not to be one of them.
If July 12th comes and goes with the Celtics having let the Pierce TPE expire, and Bogans hasn't been used to acquire anything from teams clearing salary making runs at superstars, it is likely that the window will have closed on making a significant improvement to this year's team. Assuming Bradley is still a restricted free agent, he will have a cap hold of $6,278,500. If the C's renounce Humphries and Bayless (or they've already signed elsewhere), release Bogans, Johnson, and Babb, and renounce the Lee trade exception ($2M), the MLE, and the BAE, there would be about $3.5 million in cap room, assuming that they haven't yet signed Smart and Young to rookie deals for more than their slotted values.
With this $3.5 million, they would have the ability to offer Rondo a larger extension than they currently do, as they could raise his salary for next year, and base his future salaries off the newly raised 2014-2015 salary. Currently, if they offer Rondo the largest extension they can, it would be for three additional years and $44.5 million total. However, suppose they raise his salary to $16 million for 2014 (a $3.1 million raise) and give him $16 million per year after that. This would be essentially an extension for $51 million over three years, once you factor in the extra $3 million given to him in 2014, or $17 million per year.
If Rondo would agree to such an extension, would it be worth punting on some of the other offseason moves that we as Celtics fans were hoping for? Some have already set sail (Asik and Afflalo). It wouldn't rule out the possibility of Love, if he were still on the market, but it would rule out most other options. If on July 13th, the Celtics announced such an extension, would you be okay if that's the biggest thing that happens in the offseason? It would mean that the rebuild is a little slower, but it would also mean that our best player is on board with the process.