The LoTR2 app displays on my Mac dock but the program will not open and I keep retying the WineSkin and nothing happens. Can someone please give a basic step by step on how the WineSkin Winery needs to be utilized? I have Engines Installed, new blank wrappers, but do not know how get that to play the game I downloaded.

Thank you!
Nico

Did the LOTR2 app use to work for you?

Have you tried searching online for "wineskin"? I found this website which is probably what you are talking about:
http://wineskin.urgesoftware.com/

On the very first page there is a list of "Latest Wineskin News" with the most recently dated item:
How to run in High Sierra (Oct. 23 2017)

Have you read about that yet? Is that the operating system you have? Your post is very abbreviated, you didn't give many details. If you just want a tutorial, then you'll probably find it there at that website.

Have you explored that website?

There's a link on the lefthand side of their page named "Browse Apps". Have you searched for the application you are trying to run? You stated "LOTR2", but there are a lot of Lord of the Rings games, if that's what you meant, and more than one with a sequel. If you find the game listed there, then you might also discover what other people have tried to do for that game.

I'll second thomq's remarks that you've given us precious little information for us to help you. You haven't told us about either your setup, or what Wineskin engines you've been using, or what version of OS X you're running. Simply saying, "my game doesn't work, help!" isn't going to get you very far unless you give us specific information about what exact game you're trying to run, and what you're using to run it.

That being said, in addition to thomq's links, there's a Wineskin tutorial that I wrote for Inside Mac Games here: http://www.insidemacgames.com/features/view.php?ID=595

And another tutorial I wrote a long time ago here: https://www.gog.com/forum/general_archive/gog_games_on_mac_os_x_a_how_to/page1