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Dick used to call Jason « champ », every time he felt down about something to try and cheer him up, and Jason always found it ridiculous ( he secretly liked it though, it did make him feel better).
Dick stopped using the world champ altogether after Jason died. He never called Tim or Damian champ cause to him that was his thing for Jason.
When Jason came back to life, Dick didn’t really get to call him champ anymore since their relationship was strained and he wouldn’t come to him for comfort or reassurance.
Jason started ironically calling Dick champ every time he did something dumb because he found it funny, and it honestly made Dick feel all warm and fuzzy inside.
During the time when everyone started coming to Jay for advice, he decided that channeling Dick was the best way to handle the situation, because he thought no one truly wanted him to comfort them, plus to him nothing is as comforting as his big brother. Hence the birth of « what’s wrong champ ? »
It pisses Tim and Damian off when Jason calls them champ cause they feel like he’s mocking them (after all he uses it to mock Dick) but he’s actually just trying to be a good brother which only Dick understands.
Once Caleb comes into their lives, he sometimes calls him champ when he’s doing particularly good and he feels he should praise him. Caleb absolutely loves being a champ.
For a while, Lian and Caleb started calling Dick « Uncle Champ » and that really cracked up Roy who made him a mug with « World’s greatest Champ » on it.
Now Tim is jealous to not be the world’s greatest champ. Damian still doesn’t care.