I had a friend that worked in a steak restaurant. He confirmed that anyone that ordered a steak well done didn't get the freshest steak. He also said that someone once ordered a $100+ Kobe/Wagyu (something of that stature) well done. They served him something similar, but not that steak. The chef said that anyone who would order that well done wouldn't know the difference.

It's a pretty well known steak place in SD too.
Well done is usually amateur hour.
Agree.

could've served the guy a horse saddle and he wouldn't have known.
but we are to believe that people who would serve inferior product, or even incorrect product, to a person because they ordered well done would never wipe your steak on their sack if you sent it back ?
At a high end steakhouse (which personally is the only place I eat steak) I have absolutely
ZERO concerns... Here is an example:
I ate at Del Frisco's about 2 months back. I'm almost always a Bone-In NY Strip guy when I order steak, but they had a special which intrigued me. It was 3 4oz filets, all seasoned differently and served with different sauces. When my plate arrived, the waitress asks me to slice into all 3 cuts to make sure they are to my liking, as she did to everyone else at the table. I ordered medium rare, 2 of the filets had a nice pink inside with good juices, the last was clearly overcooked and had basically no pink. Without even saying anything or asking she looks at it and says
"this is overcooked, I'll get you a new one". She left this 3rd filet on my plate and brought me out a new one less than 10 minutes later. I asked her to take the old filet, just to clear room... I feel this is common/best practice and a nice steakhouse.
I usually don't hold the tip against the waiter/waitress either... If they have asked how I want it cooked, which is basically 100% of the time, it isn't their fault. They are always apologetic and sincere so it isn't on them.