Or just use online rainbow tables much faster.
Also can take a long time just to generate many billions or trillions of passwords and it also needs many terabytes of storage.
Anyway they would be salted and use many layers of encryption so unless you have a spare million years or so and a lot of money for the electricity bill then forget it.
The messages are not encrypted using the password. Each message has it's own unique encryption key. You'd need to crack the encryption key individually for each message and password-cracking rainbow tables won't be any use to you.
(Assuming he had message encryption turned on)