A little clearity on the AN vs JIC debate. AN and all JIC fittings are 37°. SAE fittings are the only ones that are 45°. That said, I work with hydraulic systems daily with JIC fittings with working pressures of 3000-5000 psi. I think they would be plenty fine for a transmission cooler.
I has hose clamps.
I think he will survive.
BTW, the Derale coolers with the fans on them kick ass.

Especially if your boots are wet.