Summary: Based on a scene in S03E09.
The truth is: Connor once dreamed of running his father's company.
When he was little, it was just assumed that he would take over one day. It was never discussed, just spoken about like it was gospel fact. Then his mother was incarcerated and Connor was sent away, and the next time he saw his father Connor was an awkward teenager and Logan was getting married again. Then Kendall was born and it was just assumed that he would take over eventually, like Connor had never been in the running.
Then Connor's mom died, and by the time Connor crawled out of his pit of despair (he did crawl out, enough to function on a daily basis at least) he was so rich that he never had to work anyway.
Over the years he has occasionally expressed a desire to do something important for the company, and been given some bullshit like organising the catering for the RECNY ball or writing a music column.
You were never interested, his father says, and they both know it's not true, but Logan Roy's word is law and if he says it then it must be true.
He's happy for Kendall. He loves his little brother, and even if Kendall fails it will be Roman or Shiv who takes over, not Connor.
But then Kendall says Do you know what it's like, as the eldest son, to be promised something and then just (snaps fingers). And even though he loves his brother, who just nearly died in a pool accident (it was an accident, whatever Roman and Shiv may say), Connor still feels a surge of anger towards all three of his entitled, bratty siblings. Yeah Kenny, I do fucking know.
