Updated June 4, 2015 2:32 p.m. ET

On a trip to Las Vegas last month, Charlie Ergen didn’t stay long at the blackjack table. Miffed that a rule in place for the Pacquiao-Mayweather boxing match cut winners’ payouts by 30%, the Dish Network Corp. chairman and CEO walked away after only a few hands.

Mr. Ergen likes to place bets—in Vegas and in business. But he is also known for walking away from the table when he thinks it’s a bad deal.


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