I know his play wasnt great, but was mine even close to good?

[Toro]

I liked everything you did except that it was the wrong time to try it. Because he had such a big chip lead to the table and you in particular it's hard to make moves with a hand such as yours JQo. He can afford to gamble and you cannot.

[willie24]

NOTE: now that you know that he may call your preflop raise with a poor hand, your bluff here becomes much less profitable, although you should be more likely value raise hands like A9 and KJ should you ever get in this exact same situation against this opponent again.