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derrick favors trade speculation

You seem to be assuming there was a deal offered to trade Milsap & Jefferson for picks. How would that work under CBA? Jazz would have to take back salary and teams would be very unlikely to trade expiring contracts. Therefore the Warriors deal would not have happened. So your hypothetical scenario is very very unlikely to have ever been on the table. It is a nice dream, however.

It wouldn't have been one deal for both. There are always opportunities to dump borderline all-stars for picks and bad contracts. Millsap was on a fantastic contract, so there's absolutely no question he could have been cashed in for rebuilding pieces. Al's contract was more iffy, but once he was a FA, he had no problem getting paid again. Realistically, I think we could have dumped them both for rebuilding pieces without much trouble, but even if you don't believe anybody would have traded for Al, there's no doubt that teams would have been climbing over each other to acquire Sap for a pick.
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The NBA is full of teams who are just waiting for opportunities to add talent without giving up talent. I've never understood the argument that we might not have been able to dump Alsap for rebuilding pieces. There really is no doubt that those opportunities not only exist, but are fairly easy to come by, enough so that taking back long term salary really wouldn't have been necessary.
 
It wouldn't have been one deal for both. There are always opportunities to dump borderline all-stars for picks and bad contracts. Millsap was on a fantastic contract, so there's absolutely no question he could have been cashed in for rebuilding pieces. Al's contract was more iffy, but once he was a FA, he had no problem getting paid again. Realistically, I think we could have dumped them both for rebuilding pieces without much trouble, but even if you don't believe anybody would have traded for Al, there's no doubt that teams would have been climbing over each other to acquire Sap for a pick.
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The NBA is full of teams who are just waiting for opportunities to add talent without giving up talent. I've never understood the argument that we might not have been able to dump Alsap for rebuilding pieces. There really is no doubt that those opportunities not only exist, but are fairly easy to come by, enough so that taking back long term salary really wouldn't have been necessary.
It's harder to dump guys making >$8M than you think. Contenders aren't going to give up decent players and most are significantly over the cap. So they need to match whatever contracts are coming in with players they don't want. Bad contracts are less prevalent than they were. And there's an opportunity cost: if you take on a bad contract, you can't use that money for other moves. What was the BEST the Jazz could do? Take on $30M in bad contracts (i.e. players with an additional year left) and get a couple of firsts and a couple of seconds? Ummm...guess what? Jazz didn't do that at the trading deadline, but they did EXACTLY the same thing by NOT tying their hands with long-term contracts and taking on Biedrins, Rush and RJ in exchange for picks.

Sure it would have been nice to 'double-dip' and get expirings + additional picks at the deadline and then turn around and use the cap space to swing the GS deal. But there was ZERO market for Big Al. I know; I did the analysis. Contracts like Prince, Amare, etc. were available. Jazz didn't want to limit what they could do in free agency by having bad contracts on the books. As for Paul, supposedly Phoenix or Utah floated a deal involving Bledsoe for Millsap (and Burks?). Internally, I think there was still a power struggle going on between DL and KOC/Millers over the direction a rebuild would take. Maybe trading Paul was never an option...until the GS deal came about. In any case, what were the Jazz going to get - best case - for players who would be UFA's. I know, I know...Bird rights. They have value, right? I'll bet expirings and 2nd rounders from non-playoff teams (no way would anyone give up a 2014 lottery pick) or late firsts from contenders. Late firsts can always be bought...DL did that to get Gobert.

And as I mentioned, DL took the cap space he had by NOT taking on players for Millsap and/or Jefferson and trading that for picks, one of which has already been used to take Hood.
 
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