Four years ago, Andy Reid finally crossed off the big one: a Super Bowl ring. After 21 seasons as a head coach, Reid's Kansas City Chiefs defeated the San Francisco 49ers for his first Super Bowl title, cementing his legacy as one of the greatest coaches in NFL history.

Even though Reid and the Chiefs are back to their fourth Super Bowl over the past five seasons, Reid’s career in general is a testament to how tough it is to win the big one. In this iteration of a Chiefs-49ers Super Bowl, Reid is facing off against the same coach he got his first ring against — and whose career is starting to mimic Reid’s in terms of excellence without championship hardware.

Kyle Shanahan is unequivocally one of the great coaches of this era of football, routinely leading his team deep in the postseason, but he doesn’t have the elusive Lombardi Trophy. As most people who follow the sport know, Shanahan has notable history with postseason runs. He was the offensive coordinator for the Atlanta Falcons during their colossal failure in Super Bowl LI, taking some blame for how they blew a 28-3 in the second half of that game to Tom Brady and the New England Patriots.

He also led the 49ers to the Super Bowl as their head coach following the 2019 season where the Niners were a throw away from beating the Chiefs. The 49ers have also reached the NFC title game the past three seasons, losing to the Los Angeles Rams in the 2021 season and the Eagles in the 2022 season before getting over the hump to get back to the Super Bowl this year.

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There are two ways to look at Shanahan’s record in the postseason, where he’s 8-3 as the head coach of the 49ers. On one hand, it has to be frustrating to at least get to the NFC championship game in each of the four times that Shanahan has led the 49ers to the postseason. They’ve had plenty of chances to win or get to a Super Bowl (save for the Eagles game last season when they physically could not throw a pass), so to be this close without crossing the finish line is going to cast doubts among people who evaluate coaching ability through Super Bowl championships. On the flip side, the fact that Shanahan is a consistent figure in these moments means that he’s doing something right. Plenty of franchises never reach a run like this over a five-season span.

At one point, people adamantly believed Reid could never win a Super Bowl, particularly when he was with the Eagles and got close a handful of times with Donovan McNabb and never won one. Reid lost three straight conference championship games from the 2001-03 seasons before losing the Super Bowl to the Patriots in the 2004 season. In total, Reid lost four NFC title games and one Super Bowl with the Eagles before moving onto the Chiefs in 2013. Reid eventually drafted Patrick Mahomes and the rest is history that’s still being written.

Shanahan hasn’t reached that level of heartbreak with the 49ers yet, but there’s something to the idea that consistently being here shouldn’t necessarily be seen as a failure. It’s extremely hard to reach the Super Bowl multiple times without being a rockstar head coach. Reid eventually broke through and Shanahan has that same capability.

Shanahan is once again facing Reid in the Super Bowl. In a certain way, Reid is facing a younger version of himself. Both are offensive minds who define this era of football and both consistently win while putting up gaudy stats and have had success with multiple quarterbacks. Shanahan, however, remains in the position where he’s trying to get that ring that will immortalize him in NFL history. If the history of his next opponent means anything, he can break through that barrier. He knows how tough that last hurdle is going to be.

"I think the quarterback is as hard to beat as anyone who’s ever played the game," Shanahan told reporters on Thursday, referencing Mahomes, a two-time Super Bowl MVP. "The things he can do from a talent standpoint and then you pair that up with his scheme with Andy, how Andy runs a team with Mahomes’ experience now. That’s why no matter what type of game it is, whether it’s low-scoring, high-scoring, whether they’re struggling or not, they always have a chance. If they can keep it close, he is really tough to stop."

This time, Shanahan brings back a lot of the same faces from his initial Super Bowl trip as 49ers head coach. George Kittle, Fred Warner, Deebo Samuel, Nick Bosa, Dre Greenlaw, Arik Armstead and others have been in this scenario before, trying to handle Mahomes and the Chiefs. Brock Purdy, Christian McCaffrey, Brandon Aiyuk and Trent Williams are new entrants into the foray. It’s undoubtedly the most talented team of the Shanahan era in San Francisco. They’re favored in this game for a reason. Mahomes is a monster capable of beating any team, but this opportunity is as good as any for Shanahan to “prove” he can win the big one.