1/2/5NL live game 9 handed with a mandatory straddle.

100BB deep vs a player that has a lot of history with me (we're friends)

He is EP and raises to $15 and I make it $45 in the HJ. It folds around back to him and he calls. We have JdTd

Flop: Ad 8d 7x

He checks, pot is $100. We bet $75, he calls.

Turn is a total brick, 3x. He checks, we bet $130 he calls.

River is 7x & we brick our flush draw & gutshot.

He checks, we shove for $250 and he tanks for a solid 3minutes.......

Thoughts on our line? Thoughts on his range? Thoughts on his calling range on the river? Can we make him fold any weak Ax hands? Is our line believable for very strong holdings? Are we putting him in a difficult situation if he has a hand like AJ or AQ?

I think given his line it is very difficult for him to have better than top pair. I don't know for sure how he would play AK pre vs me in a 3bet pot OOP but I'm going to lean towards 4betting.