I think this is about 2 things: 1) Risk-Reward and 2) 'The NBA Economy'
1) Risk-Reward. Danny must consider the present day risk of investing a large percentage of his available capital in an excellent, but flawed player. Danny only gets a 'bargain' if he can find the right price (high enough to get him) that also fits within his big picture (but not too high). Danny's ability to speculate as to whether Rondo can become a 'climb on my back' superstar will determine just how much and how long he'll be willing to go. From Rondo's perspective, signing a contract that begins at 8 to 10 million 'risks' that he advances his game this year, stays injury-free and becomes a max player sooner rather than later. Not signing a reasonable, but lower than hoped for deal, leaves Rondo risking injury or a less than stellar year -- thus, lowering his value.
Bottom line: We need to hope that Danny's ceiling (what he is willing to pay/years) enters into the range of Rondo's agent's floor (what they are willing to accept). If these numbers are far apart -- no deal.
2) The NBA Economy. This aspect has less to do with the economy at-large, that is, the nation's economy, but rather to do with the current NBA economic reality as teams enter the FA market at the end of this year. I think this hurts Ainge's bargaining power significantly. This will be the first year in recent memory when many team will be able dole out huge bucks for FAs as many teams have been planning for the coming off-season for years. We all know this, but none of us know how it will play out. Imagine if Bosh, James, Wade... all sign with their home teams. That leaves many under the cap teams jockeying for the next best available FA. Under this scenario, guys like Rondo stand to do quite well.
Bottom line: If I am Rondo's agent, my 'floor' rises based on the anticipated NBA 'economy' of the summer of 2010. Ainge either raises his ceiling (banking on the reward), or takes the risk (risk of losign Rondo) that he'll be able to play his Bird rights into a deal for Rondo after the season. I am glad I am not Ainge.