Wouldn't it? I should think that would be the number 1 way to get insights into issues plaguing the TTC. Imagine if he had to sit through the slow order north of Bloor-Yonge every day, or had to wait 40 minutes for 5 buses to show up back to pack. You think that that shit wouldn't have gotten looked at real quick? But I doubt very much he was even aware of such problems existing.
Rick Leary was like most CEOs (with all respect to those who are not) - an opportunistic decoration that was quite content to make a whole bunch of money that he didn't deserve and meet with other important people who also make a whole bunch of money that they don't deserve while the organization floundered and both clientele and employees suffered for it. That being said, I shall reserve any judgements about whether the TTC is about to get better until we see who they end up appointing in his stead. For all we know we might end up with someone even worse. Sometimes, it's better the devil you know...