100% agree. I will reiterate what I said in another thread - you either have the nuanced big bad with a purpose, or the cruel big bad that just wants to inflict suffering. The Jailer tried to be both and in the end he was neither, being a Gul'dan until the end, then turning into an Illidan on his deathbed.
At this point I wouldn't be surprised if getting beaten was also part of the Jailer's plan. Maybe even the Dragon Isles were part of his plan. Would fit his amazing personality all based on appropriating everything ever in the lore!