I'm not sure the training tools should necessarily be included in the standard package.
It looks like Homebrew has the option to install the training tools by using a --with-training-tools switch, so I created an enhancement request for the same functionality in MacPorts:
https://trac.macports.org/ticket/51127
For the OP, you'll need to do one of the following:
1.
$ port uninstall tesseract
$ brew install tesseract --with-training-tools
2.
$ git clone g...@github.com:tesseract-ocr/tesseract.git
$ cd tesseract
$ make training
$ make training-install
Tom