So Adobe took it upon themselves to change the way you free transform in Photoshop CC 2019. Before you’d hold shift and drag and it would keep its aspect ratio instead of having your text look too tall or too thin or too wide and out of aspect ratio.
I finally figured out what they did. The aspect ratio lock is on by default now. If you hold shift it’s the reverse of what you would expect in past Photoshop versions. I honestly don’t understand why they would do this as it’s been one way all these past years and versions and I am talking years!