Itunes not syncing one song?

I have one song that will not sync to my iphone. It is a 43min long Nike running track which itunes gave away for free last year. I would love to listen to it as I run but I can't find it on my iphone. It is checked in itunes and I have it set to sync my entire music library so it should be on there. Any ideas?


If it matters I have changed my email address that I use for my itunes account since then but to my knowledge all of the older music I bought with that account still syncs perfectly fine.


Also it shows up that it is on my iphone when I look at it in itunes but not on the iphone when it is not connected. I watched it sync saying updating that track on the phone too. Nothing.

 

Yes there is a check mark.