While Kyle Shanahan has proven himself to be a very good head coach and offensive mind, he has constantly crumbled in the big games. Shanahan might end his head coaching career as one of the winningest coaches of all time. He has four double-digit winning seasons over his last five years, and he also boasts a winning record in the postseason.
In total, Kyle Shanahan is a respectable 72-55 across his seven seasons as a head coach with the San Francisco 49ers. Over his seven-year tenure, he's made the postseason four times, and in each postseason, he's got 2-1. He's lost two Super Bowls and two NFC Championship Games, clearly failing to get over the hump.
Whether it's losing in the conference championship game or the SB, Shanahan just has not been able to coach his team to the finish line. Shanahan seems to be too smart for his own good, as the 49ers' second-half collapse yet again was almost expected. For the Denver Broncos, they could have been in the same spot as the 49ers have been over the last half-decade or so.
However, it's clear that Mike Shanahan's son has reached his ceiling as the head coach, and there isn't any other goal that a team wants to accomplish besides winning Super Bowls. While the Denver Broncos have been a bad team since 2017, they and the 49ers have won the same amount of Super Bowls since that time.
And now, Sean Payton is leading the Broncos, a coach that has won a Super Bowl before and a coach who is better than Shanahan. While the potential pairing of Kyle Shanahan and the Denver Broncos would have made a ton of sense, the team might just be better off without him ever becoming the HC.
I do think at some point, it'll be time to have a tough conversation about Kyle Shanahan. Will his team ever get over the hump and win a Super Bowl? If not, none of the other regular season success or even the winning playoff record matters.