Keep in mind he only had Maero crush Jess with his truck as retribution for the brutal slaying of Carlo.
Dragging a man who had nothing to do with your newfound scar across town in a slow death is not equal to an acid tattoo.
The Boss proved he was not only not a person not to be fucked with, but that any attacks on their underlings WILL be returned tenfold onto yours.
It's psychotically brilliant; it shows your members that as boss you have their backs and will scour the earth to find and annihilate your enemies in revenge, and it shows your enemy that for as crazy and violent as you can be, the Boss is not only adept at playing the same game, but better at it than you.
Maero is so morally defeated he has to go ask Ultor for help. The Punk-Rock outlaw has to go look for the top exec suit to even the odds against the Saints and bring back morale to the Brotherhood.
Not even Gat got to 1-up the Ronin that hard following the death of Aisha. The Boss is the leader for good reason and no one will make a better crime protagonist again in contemporary game development.