Previous Team: Cleveland Cavaliers
New Team: Utah Jazz
Contract: 6 years, $70.2 million
Shock Value: 8

Dan Gilbert became the Cavs majority owner a year too late. If there ever was a situation where a Dan Gilbert-type letter would be justified it would be for Carlos Boozer’s departure. The Cavs declined Boozer’s option so they could sign him to a bigger deal that both sides already agreed on. Boozer and the GM at the time, John Paxson, even shook on it. Boozer ultimately broke his promise and signed a bigger contract with the Jazz. Imagine if Twitter were around back then.