When Matthew Dellavedova entered restricted free agency during the summer of 2015, he was seeking a three-year, $10 million deal to remain in Cleveland. Instead, the Cavs forced him to take their qualifying offer of $1.1 million in a miscalculation that has haunted them since.



At the time, the Cavs were rightfully concerned about the luxury tax. Dellavedova earning $3 million in 2015-16 instead of his actual salary would’ve added another $7.5 million to their already league-high $54 million tax bill. Instead, Dan Gilbert saved nearly $8 million in taxes during the championship season while unknowingly creating a long-term void on the roster they have been unable to fill the last two years.



Dellavedova’s departure, coupled with Mo Williams’ unexpected retirement, left the Cavs without a backup point guard for most of last season until they picked up Deron Williams in March. While the signing looked like a shrewd financial move at the time, Williams was such a disaster that he played himself out of the league. Adamant they wouldn’t make the same mistake twice, the Cavs quickly snatched up Jose Calderon at the start of free agency this season for the league minimum.



Yet, history has somehow repeated itself. Derrick Rose, the oft-injured point guard the Cavs also picked up for the league minimum, injured his ankle in the second game and hasn’t been the same since. It’s clear now that Rose tried to rush back too soon. He was shut down again after five ineffective games, and the team announced Friday he will now be out for another two to three weeks and have his left foot immobilized in a boot because the ankle just isn’t healing.



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