Kyle Shanahan has given the 49ers plenty of winning football, but the ring still hasn’t arrived. That’s what makes the debate so brutal: which of his teams came closest to being the one that should have finished the job?
The cleanest answer might be all of them. Shanahan has fielded multiple teams good enough to make a real run, and the 2021 group deserves a nod as an honorable mention after coming within minutes of a Super Bowl trip to face the Cincinnati Bengals. But if you have to pick one, the case gets interesting fast.
Start with 2019, the team that looked like it might be ahead of schedule after two losing seasons under Shanahan. San Francisco surged to a massive lead in the NFC before taking its first loss to Seattle on Monday night at Levi’s Stadium. The roster got a major boost from Nick Bosa, Dre Greenlaw and Deebo Samuel, and each of them mattered at different points.
That team had real bite. Raheem Mostert carved up the Packers in the NFC Championship Game, and the 49ers entered the Super Bowl with a 10-point lead before everything unraveled.
Kansas City finished the comeback and handed Andy Reid and Patrick Mahomes their first championship. It’s the kind of loss that lingers because the game was there to be won and slipped away.
The pass rush of Bosa, DeForest Buckner, Arik Armstead and Dee Ford also feels like a group that may not be duplicated during the Shanahan era, and Joe Staley’s final game as a 49er adds another painful layer.
Then there’s 2022, the strangest ride of the bunch. Trey Lance started the season before breaking his ankle.
Jimmy Garoppolo, described in camp as a “cardio king” while waiting for a trade, stepped in, stabilized things, and then broke his foot. That opened the door for Brock Purdy, the last pick in the draft, who took over against Miami and launched his own legend.
From there, the 49ers handled Seattle in the Wild Card round and got past Dallas in the Divisional round. Philadelphia was next, with a Super Bowl berth and a rematch with the Chiefs hanging in the balance.
Then Purdy got hurt early, Josh Johnson was injured too, and San Francisco ran out of quarterbacks. That game helped create the three-quarterback rule, and it stands as the biggest “what if” season of Shanahan’s tenure.
But the strongest argument belongs to 2023. This is the one that feels like it had everything lined up until the very end.
San Francisco’s injury luck was as good as it had been under Shanahan until the Super Bowl, when Jon Feliciano and Dre Greenlaw went down. The regular season was almost spotless: the 49ers lost three games, and all three came in the same stretch.
Christian McCaffrey was unstoppable, Purdy played some of his best football, a wide receiver wearing number 11 was insanely efficient, and the team answered the old “can’t come back” label with two playoff wins, including the wild NFC Championship comeback against Detroit.
The Super Bowl itself was packed with moments. Jauan Jennings threw a touchdown pass.
McCaffrey fumbled on the opening drive. The defense held up for most of the night.
Ji’Ayir Brown intercepted Mahomes. Jake Moody set the Super Bowl record for the longest field goal.
Ray-Ray McCloud’s special teams mistake hurt badly. And in the end, the 49ers became the first team to score in overtime and lose a Super Bowl.
That’s why 2023 gets the nod here. It felt like the season where everything finally aligned, right up until it didn’t. The others have their cases, but this one had the clearest path and the cruelest ending.
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