S.P.
I had the same problem with my oldest. I made the mistake of holding him until he went to sleep from the beginning. Also, he never used a binky. When I finally decided to put him down awake, I had the problem of him crying it out. Usually, he'd cry until he sicked up. It was horrible. I then tried a small, safe toy. He'd play with it, in his bed until he went to sleep. He needed the help to self-soothe. It worked for both my kids. I hope this helps. Oh, I used matchbox cars for the toy. It worked for them. My youngest is nine and still takes a toy to bed to play with before he goes to sleep.
One other thing you might whant to try is putting him to bed a little earlier. He may be over tired. I hope this helps. Good luck!!!!