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The best place to start this is with a tale of two cities. Last summer, both Toronto and Cleveland had decisions to make as their marquee players were to become free agents at the end of the season. The Cavaliers believed reasonably that LeBron James could (would?) return to them, so they focused on making the team better with him as the focal point.
On the other hand, while absolutely affected somewhat by hindsight, it still looked intensely unlikely that Chris Bosh was staying in Toronto beyond 09-10.
Moving forward, both teams held firm on their player. While both ended up leaving their old homes, Cleveland appeared to have a fighting chance with James, while Toronto did not even get a phone call from Bosh after the season ended.
Cleveland's decisions (in terms of this narrow point) made sense, as they knew James was an atypical commodity for them and they reasonably believed they had a chance to keep him.
In comparison, Toronto did not maximize on their investment as they did not even make the playoffs in the year they kept Bosh and got the same pittance as the Cavaliers, partially thanks to Miami’s cap situation and all three max guys taking a little less money.
What Denver can learn from this summer is the same lesson we learned from Kenny Rodgers- you have to know when to hold ‘em, know when to fold ‘em.
Once Carmelo Anthony shifts from the LBJ situation where you feel you have a fighting chance in free agency to a Bosh situation where that chance is illusory or non-existent, it is time to sell. That is a decision only they can make, but the timing is extremely important here.
The Carmelo situation is particularly interesting because there are three distinct time periods where he could change addresses, each of which has its own advantages and disadvantages for all involved parties.
The easiest time period is the one after this coming season. If Melo decides to leave, the best guess is that the price would be similar to Bosh and James, with Denver having additional leverage (and assets back) if the new team has less financial flexibility than Miami did.
The second circumstance is trading Carmelo before this season starts. One major change here is that Carmelo would be able to sign an extension with the trading team right now, which both decreases the long-term risk for him and his future team and increases what he can yield in a trade as it comes to Denver. Beyond that, the third option is to trade Carmelo to a team with an extension, much like the Kevin Garnett deal in the summer of 2007. Here, Denver has to cater to Melo’s whims to a degree since he can put the kibosh on any deal by refusing to sign an extension with that team. That said, they could have some leverage if the team would not have the ability to sign Carmelo outright in 2011 as well as a risk premium since they would have a franchise player locked in for at least the next four seasons.
The final option is to trade Anthony during the season without an extension, yet that is awkward because it is unlikely to achieve the goals of any party involved, though it is possible that Denver could end up getting more cutting bait at the trade deadline than they would get in the summer.
http://www.realgm.com/src_feature_pieces/963/20100827/the_gambler/
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