Problem with flipping and cropping images

Hi!

Lately I've tried to 'flip horizontal' two images but they are changing when I flip them or crop them afterwards. Images posted below.

When I flipped the image of the head and shoulders guy after cropping, he lost a shoulder.

With the judge, I cropped him first, then flipped him and the background on one side of his arm would return while clipping off part of his other arm. I tried flipping the whole image first and then cropping him, but it didn't help.

Below are images of the following:

1. Original image

2. Image flipped

3. Image cropped to the edges of their arms and then released (i.e. I click outside of image to see the cropped image). I have full reign of the cropping tool (i.e. I can move it to where I want), but as soon as I release it , this is what it does.

Hope you can help!

Jacinta