Suppose you are out on bail facing felony charges that could earn you a long prison sentence, but you also think you would have a decent chance of getting acquitted or at least getting a much lighter sentence if a few specific witnesses for the prosecution were not cooperating with the prosecution.

Intimidating those witnesses might then be worth it even if getting caught at that means spending the time between now and the end of your trial in jail.

From another comment it appears that he is someone who would take a bet if it is slightly in his favor, even if the reward is only a little more valuable than the risk.