It’s a question that still stings for folks in Southern California, usually asked over a beer or during a nostalgic look back at the 2000s era of the NFL. Did the San Diego Chargers win it all? The short answer—the one that hurts—is no. Not a Super Bowl, anyway.
They came close. They had the talent. They had the lightning bolts on the helmets and some of the greatest players to ever lace up cleats. But the trophy case in San Diego remained frustratingly empty of Lombardi Trophies until the moving vans arrived in 2017 to take the franchise up the I-5 to Los Angeles.
People often forget how dominant those teams were. We’re talking about a franchise that defined high-flying offense for decades, yet somehow, the timing was always just a little bit off. If you’re looking for the championship glory, you have to go way back, before the NFL was even the NFL as we know it today.
The 1963 AFL Championship: The forgotten peak
Basically, if you want to say the Chargers won a "world" title, you have to look at 1963. This was the American Football League (AFL) era. Before the merger. Before the Super Bowl was a "thing."
Led by the legendary coach Sid Gillman—the guy who basically invented the modern passing game—the Chargers absolutely dismantled the Boston Patriots 51-10. It was a masterpiece. Keith Lincoln went nuclear in that game, racking up 329 yards of total offense. Honestly, it’s one of the most dominant performances in professional football history. But because it happened in the AFL three years before the first Super Bowl, it doesn't count in the eyes of many modern fans.
That 1963 squad was revolutionary. Gillman was using motion, downfield passing, and sophisticated schemes that looked like they were from the future. They were the Kings of the AFL. But then the merger happened, the Super Bowl era began, and the luck started to turn.
The 1994 miracle and the Super Bowl XXIX disaster
The closest the city ever got to that elusive Super Bowl ring was the 1994 season. It was a weird, magical run. This wasn't a team of superstars like the later squads. It was a blue-collar group led by Stan Humphries at quarterback and the late, great Junior Seau on defense.
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They weren't even supposed to be there.
The AFC Championship game against the Pittsburgh Steelers is still the stuff of legend in San Diego. The Chargers were heavy underdogs. They went into Three Rivers Stadium, stood their ground, and won 17-13. Dennis Gibson knocking down that last-second pass in the end zone is probably the single greatest moment in franchise history.
Then came Super Bowl XXIX.
It was a nightmare. They ran into the San Francisco 49ers buzzsaw. Steve Young threw six touchdowns. The Chargers were down before the seats were even warm. The final score was 49-26, and it wasn't even that close. It felt like the air had been sucked out of the entire city. You had a whole generation of fans who thought, okay, we finally made it, this is our time, only to realize they were playing against one of the greatest teams ever assembled.
Why the 2006 team is the ultimate "what if"
Ask any Chargers fan about 2006. Watch their eyes glaze over. It’s a traumatic topic.
That 2006 roster was, on paper, arguably the best team of the 21st century to not win a ring. Look at the names. LaDainian Tomlinson (LT) in his prime, setting the single-season touchdown record with 31. Antonio Gates at tight end. A young Philip Rivers. A defense featuring Shawne Merriman and Jamal Williams. They went 14-2. They had home-field advantage.
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Then the New England Patriots came to town for the Divisional Round.
The Chargers should have won. They were better. But a series of bizarre mistakes—including a fumbled interception by Marlon McCree that would have sealed the game—led to a heartbreaking 24-21 loss. It cost head coach Marty Schottenheimer his job despite a 14-2 record. People still argue about that firing today. It felt like the window slammed shut right then and there, even though they remained competitive for years afterward.
The Rivers, Gates, and Tomlinson era
It’s genuinely wild to think that Philip Rivers, LaDainian Tomlinson, and Antonio Gates played together for years and never even made it back to a Super Bowl.
- LaDainian Tomlinson: 13,684 rushing yards, 145 rushing touchdowns. A first-ballot Hall of Famer.
- Antonio Gates: 116 career touchdowns, the most ever for a tight end.
- Philip Rivers: Over 63,000 passing yards.
They were consistently a top-five offense. They won the AFC West four times in a row from 2006 to 2009. But every time January rolled around, something went sideways. Bad injuries (Rivers playing the 2007 AFC Championship on a torn ACL), missed field goals (Nate Kaeding), or running into the Tom Brady/Peyton Manning gauntlet.
The narrative that "the Chargers always find a way to lose" started to cement itself during these years. It wasn't that they weren't winning—they were winning a lot—they just weren't winning the last one.
The move to Los Angeles and the end of an era
By the time the team moved to Los Angeles in 2017, the question of whether the San Diego Chargers would ever win a title became a moot point. They weren't the San Diego Chargers anymore.
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The move was messy. It broke the hearts of a loyal fanbase that had endured decades of "almosts." Since moving to LA, the team has had flashes of brilliance with Justin Herbert, but that specific identity—the San Diego identity—is gone.
When people ask if the San Diego Chargers won, they are often searching for a sense of validation for a city that loved its team. San Diego is a "sports-cursed" city in many ways, with the Padres also chasing that elusive first title. The Chargers' departure without a trophy felt like a final insult to a city that had given them so much.
Real talk: Why didn't they win?
There isn't one single reason. It’s a cocktail of bad luck, coaching changes, and running into legendary dynasties. In the 80s, the "Air Coryell" Chargers were stopped by the Raiders and the Dolphins. In the 2000s, it was the Patriots.
Some point to ownership. The Spanos family has always been a polarizing topic in San Diego. Critics argue they didn't spend enough on the right pieces or made poor front-office hires at critical moments. Others say it was simply the "Chargers Curse."
Whatever you call it, the record books show a 1963 AFL title and zero Super Bowl rings.
How to track the Chargers' legacy today
If you want to dive deeper into what happened to this franchise and why they never quite got over the hump, there are a few things you should check out:
- Watch "The Missing Rings" documentary series: There is a great episode specifically on the 2006 Chargers. It breaks down the New England loss in agonizing detail.
- Look up the 1963 AFL Championship film: It’s available in bits and pieces on YouTube. It shows just how ahead of his time Sid Gillman was.
- Study the 2000s draft classes: The Chargers under AJ Smith were incredible at drafting. Understanding how that talent was assembled—and then dissipated—is a masterclass in NFL team building.
- Visit the Pro Football Hall of Fame: See the busts of Seau, Tomlinson, Fouts, and Alworth. It’s a reminder that while the team didn't win a Super Bowl, the individuals were some of the best to ever play the game.
The San Diego Chargers didn't win the big one. They gave the city 56 years of excitement, some of the most iconic jerseys in sports history, and a lot of "what if" stories to tell at the bar. For many, that legacy of being the "greatest team to never win" is its own kind of fame, even if it doesn't come with a ring.