Was it ever explained in the film or in a prequel comic? I don't recall seeing anything explaining where Simmons sudden wealth came from. In ROTF, we saw him working with his mother in the family deli. But now in DOTM, he is living the life of luxury in a mansion with his personal bodyguard Dutch, as well as a maid and other workers. He has self portraits of himself painted featuring him in Egypt. Was his wealth simply a result of the book he wrote? To be honest, I feel like the book had nothing to do with his wealth at all, because it seemed Simmons's lifestyle was far to extravagant to be caused by 1 book being on the best-seller list.
Maybe he purchased those teeth that the guy that worked with him in the Deli needed and sold them to someone else for a Rip-Off Price. THEN he must have made the book.
His Books were a best seller and that made him rich, it was confirmed by TheLastPrime (who is not working on the movie, but shared with us alot of reiable info of DOTM, like Optimus trailer would carry Optimus weapons and other stuff) during filming of the movie that Simmons will be rich in the Movie because of writting books of his experiences with the autobots Simmons only appearance on DOTM Tie in Prequels was on covergence, but that one takes place Years Before the first movie happened
Yes it did, a book about "aliens" he shilled it in the spot with Bill O'Riley on camera in the movie.
Govnerment paid him to be quiet...and then he went out and published that book of his. Simmons knows: fear=people willing to spend $30 for a hardcover book that promises answers to their problems.