Thoughts regarding encryption & non-securely deleted files

Let's say you have a USB drive, non encrypted, from which you over the years have deleted a bunch of files - non-securely. Since you realize that the files are sensitive, you now choose to encrypt the drive with the right-click -> Encrypt function. Furthermore, you also set the trash can to always securely delete files from now on.
What worries me about this scenario are the old files that were deleted non-securely, before encryption: If someone would steal the drive and attempt to restore data that hasn't yet been overwritten, would those deleted files be accessible to that person? Or have the encryption effectively scrambled those old files as well?
I know that the best option is to do a 7-pass format and encrypt the drive and then move your files to it, but that isn't always an option (you might not have space to store files temporarily somewhere else, for example).
An other thing about "secure delete" which isn't really clear: Does the secure delete also overwrite previously deleted files or just the ones from the point in time when you turned on the setting?

If someone would steal the drive and attempt to restore data that hasn't yet been overwritten, would those deleted files be accessible to that person?
No. Every block on the drive will be encrypted, including free blocks.

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