Apple - Wine won't open any programs

The real problem was that I had removed the Z: drive which pointed to my root directory. After adding the Z: drive back using winecfg, I was able to run Windows programs from any location again.

I finally got it fixed. I just deleted the .wine folder, ran winecfg again, and everything started working.

rm -rf ~/.wine
winecfg

Sometimes after trying this solution, I still have this problem. I have found that moving the program to inside the ~/.wine/drive_c folder fixes this.

You can consider installing Wine.app via brew-cask, e.g.

brew cask install wine-stable

By using the macOS app, it can handle executable and file locations in a better way.

There is also the WineBottler app which comes with Wine.app as well.