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Note: I know this is an old thread, and am just posting to help anyone else who stumbles upon this thread.
First of all: Wine (just plain wine) is NOT available for Mac, so that leave you with Wineskin, WineBottler, PlayOnMac, or CrossOver.
Wineskin and WineBottler are intended for creating wrappers, which is basically converting it to a Mac application.
Wineskin gives you more customization over your wrapper.
WineBottler also comes with a system that lets you just run any exe on mac just like that.
PlayOnMac lets you download and run supported apps easily, but isn't good for just any exe.
Winebottler Mac Os Catalina
CrossOver is paid software.
Updating Winebottler Environment
If all you want to do is run exes with right-click>Open With, than install WineBottler.
With 32-bit program support going away on the Mac with Catalina we need to start seriously figuring out how to have WINE run on these newer systems so that reasonable instructions can be provided.