The best chance the Cowboys had to win a Super Bowl was the 2007-2008 season. The Cowboys went 13-3, had the first round bye and then lost to the wild card Giants in the divisional round of the playoffs. I think had they not choked to the Giants, they would have won that Super Bowl. Romo choked, and others choked as well,
I thought they had a good chance in 2016-2017 but lost a tough game to Aaron Rodgers and the Packers. It was a game they could have and should have won. The defense let them down at the end of the game but they were in that game for 60 minutes. Dak did not choke that day. He actually led them back from a 28-13 deficit to tie the game with 58 seconds on the clock until the Packers kicked the game winning FG with 3 seconds on the clock. Rodgers threw a miracle to the sideline for a huge 1st down on that game winning drive.
Since then, they really haven't had what I would call a SB worthy team. In 2023 they were close except they had issues on defense that were evident the entire year. GB exploited their inability to stop the run. Aaron Jones, who always seemed to give the Cowboys fits, did so again. But in the off-season rather than fix the 2 holes in the Cowboys lineup, they actually made things worse.
And here we are. If the defense did not choke in 2016-2017 to give the Packers the win, I wonder what we would be saying about Dak now.