Per the OED: Reckless adj
Heedless of or indifferent to the consequences of one's actions; lacking in prudence or caution; willing or liable to take risks; rash, foolhardy; irresponsible.
For your example, you would need to change it slightly as this isn't a noun:
Tom is so reckless! He knows this will cause him trouble as it has in the past, but he just does it anyway.