Dean- You were on a hunt and broke your arm. Hurt like hell.
Sam- Your wrist. This is why Sam gets things in high places.
Castiel- Collarbone. A demon attacked you on a hunt and snapped your collarbone. Cas, of course, fixed it.
Adam- Your femur. It hurt like hell and you were in a wheelchair for a long time, then crutches a long time. This is why you don't play sports with the boys.
Gabriel- Pinky. You just grabbed a splint and some tape knowing the hospital wouldn't do anything. They never do anything for this stuff.
Lucifer- Big toe. He's just so competitive and he wouldn't give you the chance to do anything. Therefore, you broke your toe trying to get the soccer ball away from him.
Crowley- You broke your knee. Four months on crutches plus six months of physical therapy was worse than it sounds.
Michael- Your nose. Someone made you mad so you got in a fight and they punched you in the face causing the broken nose. Michael was not happy.
Sammandriel- You broke your tibula. Not exactly sure how.
Kevin- You dislocated your shoulder because you were wrestling with him. That boy plays smart,
Chuck- Ankle. You fell down the stairs. It's an embarrassing story you'd rather not share.
Ash- Forearm. Again, not a story you prefer to share with the world.
Gadreel- Middle finger. Now you can't flick Dean off.