I think it might have been when Troy was named to the Hall of fame. Not the day he went in, but the day he was named as having been accepted. Jimmy Johnson was quizzed about Troy and his stats. I am paraphrasing here, but it went something like this.
Troy could have put up Marino numbers if we needed him to. But Troy sacrificed personal stats and didn't complain, because our offense was get ahead with the pass then run the clock out with Emmitt.
The Romo versus Aikman debate rages and will do so for a few decades.
People suggest Emmitt made Troy in this thread. I disagree. Irvin had a hand in the results Troy enjoyed. But to be sure Troy was so dang accurate, he influenced Irvin's career.
One of the aspects of Aikman was his belief in his receivers. You drop a couple of easy passes and you may never see the ball again. If you recall the 1992 NFC Championship game, there was a moment which defined Aikman and his belief in his guys.
Aikman has said in a different interview he saw Harper and thought, "I've just got to trust this guy." So he threw the ball to Harper and history was made and the legend began on that play. But Aikman had to know you would catch the ball, or at least know to play defense if the defenders was making a play. Later in his career, even before Irvin went down he struggled with the second receiver once Harper was gone.
A watershed moment for Jerry was when he brought Rocket Ismael to the team. He had poor boy'ed the second receiver for several years, but understood at one point he needed someone to take the pressure off Irvin. Ismael and Irvin were tearing the league up, but in the Eagle game Irvin went down and that was the season. The next year Jerry went after Galloway. Some suggest that was a mistake, but Jerry had learned the passing game needed two receivers that opened each other up.
So while some say Romo was better, you need to look beyond Romo's highlight reels. Romo was magic, but sometimes what you need is steady. This is why I think Troy was better. Especially when you factor in the 2014 season where Dez was play making and Murray was chewing up the clock and staying in front of the chains. Romo had the team twice. 2007 and 2014.
But to be sure, Romo also had Garrett in 2014, and that gives Aikman a HUGE advantage.
A little more on the 92 game.