Is there a way to create a rule for Apple Mail that when a certain person is a recipient, make the email plain text?

My boss has a blackberry and when I send pdf attachments and copy him, he cannot see the attachments.  I forget to make the email plain text before sending it to him.  I can use Thunderbird as my client and it works fine but it is not linked to the other apps on my mac like Apple Mail.  Can I make a rule or something for Mail so that when his email address is a recipient of the email, it will send as plain text to him?

I don't think so. Not without setting up an AppleScript and I am not proficient with those.
You can, however, set the follolwing in Mail > Preferences > Composing
Responding: Use the same message format as the original message.
But that would only be for responding to messages sent from his Blackberry.

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