Boss fights are the best way to test your mafia's strength. These special jobs are multi-round fights against the city's roughest cops and rival criminals. Each round, you can choose to either attack or run away. The fight ends when either side's health reaches zero, or you decide to run away from a fight you don't think you can win.
Enter into these fights with caution, as running away will cause you to lose a portion of the Risk amount and losing to the boss will cost you the entire Risk amount. This increased risk, however, comes with increased reward. Since bosses are much harder than a regular job, they give much more experience per energy as well as dropping an amount of cash that is based on your current total.