1. Sending Kurt Thomas and taking on RJ's 30M 2 Years contract when he was a MLE player at best. Fortunately, he accepted to out of the second year and was resigned for 39M over 4 years. But the Spurs avoided paying luxury tax. The Spurs then unloaded his contract taking on Jack's contract which was a year shorter and giving up a first rounder.
2. Taking on washed up Steve Smith's 19M / 2 years and giving up Kerr in the same S&T. It was better to let DA walk, keep Kerr.
3. Offering Malik Rose 42M for 7 seasons. To unload the contract after 3 sesons, the Spurs gave up 2 first rounders. Malik was missed vs the Mavs in '06 and one of the first rounders was David Lee.
4. Offering Scola's rights to unload Butler's contract, that wasn't that bad.
5. Taking Mercer in a trade for almost 7M, he was cut after few games in the season.
I hope it wont, but that last Manu's contract could make the list some day.

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