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
(..) Lannisters made you one of the great lords of Westeros. Yet, here you are in the North, undermining them. Why gamble with your position? Every ambitious move is a gamble. You gambled when you drove a dagger into Robb Stark's heart. It appears that your gamble paid off. You're Warden of the North. (..)2015 TvShow: Game of Thrones Title: High Sparrow Season: 5 Episode 3