I felt bad for Jake...
I mean, he was a good boyfriend (as far as we could tell) to Jessie - he fed her drugs for a while (a friendly hookup!) then got her clean. She threw him away - for what? For $50K and a vacation to Cozumel? So what if he could be a possessive controlling criminal? He was a good BOYFRIEND!
Also, toward the end, we see he's just a pawn in the larger game - though, perhaps a slightly evil one. But still - she didn't know that!
After his conversation with her on the beach, i saw the real devotion Jake had for Jessie - perhaps a possessive jealousy, but that was Terry's problem too - everyone wanted Jessie a little TOO much.
And frankly, who can blame them - 1984 Rachel Ward was a the BOMB.