The mayor is 'gambling' that the new policies will help rather than hurt the city.
The company is 'gambling' [='betting, risking'] everything 'on' this strategy.
people who lost money 'gambling' in the stock market
(..) Hey, c'mon. He can't lose. I think the pit boss is watching him. Are you okay? I'm such a klutz. I get so nervous when I gamble. I'm so silly. Hold on a bit. Let's just take it easy. This is my wife. It's hurting./ Does it hurt?/ Yeah. (..)2009 The Hangover
(..) Is he all there, like, mentally? I think so, he's just not guy, and he's kind of weird. Should we be worried?/ No. Tracy did mention that we shouldn't let him gamble or drink to much. Jesus, he's like a gremlin. Comes with instructions and shit And one water. I'll go with Melissa?/ Oh, yeah. (..)2009 The Hangover