5 Best NFL Head Coaches To Never Win A Super Bowl—And The 5 Worst Who Actually Won

In the NFL, there is one measuring stick that ultimately separates the good coaches from the great ones… and that is the Super Bowl.

Win one, and you are a legend. Your bust goes to Canton. Your name gets mentioned with the all-time greats.

But here is the thing… winning a Super Bowl does not always mean you were the best coach in the building. And not winning one does not mean you were not elite.

So today, we are going to separate the deserving from the lucky. Five coaches who never won it all but absolutely should have… and five coaches who got their ring but maybe did not deserve it.

Let us get into it.

Do all these head coaches deserve a Super Bowl win?

BEST WITHOUT A RING: Marty Schottenheimer, Head Coach

200 regular-season wins—the most for any coach in NFL history who never won a championship. And somehow… he is not in the Hall of Fame… which, of course, makes him the only eligible coach with 200-plus wins who is not in Canton.

Schottenheimer coached for 21 seasons across Cleveland, Kansas City, Washington, and San Diego. And look… he knew how to win. At least in the regular season.

His teams won 8 division titles and made 13 playoff appearances. “Martyball,” they called it… conservative, run-heavy, grind-it-out football.

But January… That is where it fell apart.

5 and 13 in the playoffs. Three AFC Championship appearances, three losses. And two of those losses… man, two of those losses were gut-wrenching.

You know the names. “The Drive”… 1986 AFC Championship, Elway goes 98 yards with 37 seconds left to tie the game. Cleveland was right there. 

Then the very next year, Earnest Byner fumbles at the 3-yard line in the championship game with a chance to go to the Super Bowl, and it just… slips away. 

And lest we forget… in 2006, Schottenheimer went 14 and 2 with the Chargers. Best record in football. 

Only to lose in the playoffs to the Patriots, and then get fired. 14 and 2, and they showed him the door. But even when he passed, there was still some controversy that was sparked.

WORST WITH A RING: Barry Switzer, Head Coach, Dallas Cowboys

Now let us flip the script completely…

If you want the perfect example of “right place, right time”… look no further.

Barry Switzer won Super Bowl XXX with the Dallas Cowboys in 1995. And on paper, that looks great. But let us talk about what actually happened.

Jerry Jones fires Jimmy Johnson. You know… the guy who had just won back-to-back Super Bowls with Dallas. The guy who built that roster, despite what Jerry wants you to think… The guy who drafted and developed Troy Aikman, Emmitt Smith, and Michael Irvin.

And who does Jerry bring in? His old college buddy, Barry Switzer.

Switzer walked into one of the most loaded rosters in NFL history. “The Triplets” were in their primes. The dynasty was already rolling. All Switzer had to do was not screw it up.

And look… even Jerry Jones admitted it. He said “any coach” could have won with that roster. Those are his words, not mine.

So Switzer wins the Super Bowl in his second season. Great. What happens next?

1996… 10 and 6, lost in the divisional round. 1997… 6 and 10. First losing season for the Cowboys in a decade. Switzer resigns, never coaches in the NFL again.

Four seasons. One championship that anyone could have won. A .500 coach wearing a ring he inherited.

BEST WITHOUT A RING: Dan Reeves, Head Coach

Four Super Bowl appearances… and four losses.

Three trips with the Broncos in the late 80s, one more with the Falcons in 1998. And here is the brutal part… these were not close games. These were not last-second field goals or fluky plays.

Reeves got blown out. In those four Super Bowls combined, his teams were outscored 163 to 79. Super Bowl XXIV against the 49ers… 55 to 10. That is still the worst loss in Super Bowl history.

The trend was bizarre… because the man could coach—as evidenced by his two-time Coach of the Year honors and the fact that he led three different franchises to the playoffs. 

But that fourth Super Bowl loss… that one had to sting in a different way. 

Reeves brings his Falcons to the big game. And who is waiting for him? The Denver Broncos. 

I mean… losing the Super Bowl is bad enough. Losing it to the franchise you made great? That is cruel.

WORST WITH A RING: Brian Billick, Head Coach, Baltimore Ravens

Oh, this one is rich.

Brian Billick was hired by the Ravens as an “offensive genius.” His Minnesota Vikings offense had just set the NFL scoring record in 1998. This guy was supposed to bring that firepower to Baltimore.

So what happened?

Billick won Super Bowl 35… but with one of the worst offenses in NFL history.

The 2000 Ravens went five games without scoring a single touchdown. 

Their entire game plan was “hand it to Jamal Lewis and let Ray Lewis and the defense handle the rest.”

Luckily, the defense was actually incredible. 

They set the record for fewest points allowed in a 16-game season… 165 points. That unit was historic.

But here is the thing… Billick had nothing to do with that defense. He was an offensive coach who won with defense.

After that championship, Billick continued to cycle through quarterbacks… and never developed a franchise guy. 

Until he finally got fired after a 5 and 11-season run in 2007.

The “offensive genius” who won it all with defense and then never figured out offense again. Go figure.

BEST WITHOUT A RING: Bud Grant, Head Coach, Minnesota Vikings

Bud Grant was another coach with a dubious 0 and 4 mark in Super Bowls…

But here is the difference… Grant had some of the worst luck in terms of opponents. He was not just losing to good teams; he was losing to dynasties.

Super Bowl 4 against the Chiefs, Super Bowl against the near-perfect Dolphins, Super Bowl 9 against those dominant Steelers, and finally Super Bowl 11 against the Raiders. 

Teams that you’d have to play an absolutely perfect game to beat. Those were juggernauts.

It is a shame he never got over the hump, too… Grant was a winner at every other level… he even won four Grey Cup championships with the Winnipeg Blue Bombers up in Canada. 

But no Super Bowl ring. The Vikings patriarch defined that franchise for nearly two decades, and the one thing everyone remembers is 0 and 4 in the big game.

WORST WITH A RING: Don McCafferty, Head Coach, Baltimore Colts

Don McCafferty won Super Bowl 5 in his very first season as a head coach. He’s in the Mount Rushmore of Dallas’ coaches’ history. Impressive, right?

Maybe at a glance, but let’s talk about that Super Bowl.

Super Bowl 5 is known as the “Blunder Bowl.” 

Eleven combined turnovers between the two teams. The Colts alone committed seven turnovers… and still won 16 to 13 on a last-second field goal.

It was the sloppiest Super Bowl ever played. And McCafferty’s team was the sloppier one. They just happened to win anyway.

Also worth noting… McCafferty inherited that Colts roster from Don Shula. You know, the winningest coach in NFL history. Shula left for Miami, handed McCafferty a Super Bowl-caliber team, and McCafferty won with it in his first year.

The very next season? Lost the AFC Championship 21 to 0. To Don Shula’s Dolphins. The guy who built the roster came back and shut them out.

Then, in 1972, McCafferty was fired five games into the season for refusing to bench Johnny Unitas.

When all was said and done, he coached just four years in the NFL.

BEST WITHOUT A RING: Don Coryell, Head Coach

Here is a guy who changed football forever… and never even made it to a Super Bowl.

Don Coryell invented “Air Coryell”… and if you do not know what that means, just know that every modern passing offense you love traces back to this man. His San Diego Chargers led the NFL in passing yards for six straight seasons from 1978 to 1983. That is still an NFL record.

His coaching tree? John Madden. Joe Gibbs. Mike Martz. Norv Turner. Guys who went on to win championships running versions of what Coryell created.

But Coryell himself? Two AFC Championship losses. One to the Raiders in 1980, one to the Bengals in 1981. Never got over the hump.

But here is what really gets me… Coryell did not get into the Hall of Fame until 2023. Thirteen years after he passed away. The godfather of modern offense had to wait over a decade post-mortem for recognition.

Better late than never, I guess. But it would have been nice for him to have been there for it.

WORST WITH A RING: Gary Kubiak, Head Coach, Denver Broncos

Speaking of being in the right place at the right time…

Gary Kubiak spent eight years with the Houston Texans, where they were extraordinarily mediocre.

Then he goes to Denver… and wins a Super Bowl in his first season.

So what happened? Did Kubiak suddenly become a genius?

Not exactly.

Kubiak walked into a situation with one of the best defenses in the NFL. Von Miller, Aqib Talib, Chris Harris Jr… Wade Phillips had that unit playing at an elite level. 

Kubiak’s career record is barely above .500… 82 and 75. He resigned after the 2016 season, citing health concerns.

The ring is real. But the context—he was carried by a defense that he had nothing to do with.

BEST WITHOUT A RING: George Allen, Head Coach

George Allen has the highest winning percentage of any coach without a Super Bowl championship.

In fact, that mark is the third-highest in NFL history, behind only Vince Lombardi and John Madden.

And he never had a losing season. Not once. Twelve seasons in the NFL between the Rams and the Redskins, and every single year his team finished above .500.

Seven division titles. Two-time Coach of the Year. The man flat-out won football games.

So what happened?

Well… he only made it to one Super Bowl. Super Bowl 7 against the 1972 Dolphins. And look, I cannot even really knock him for that loss. That Dolphins team went undefeated. 17 and 0. Only perfect team in NFL history.

Losing to them 14 to 7? No shame in that.

His system worked in the regular season year after year… and it was able to get him to a Super Bowl, but it was never sustainable enough to get him and his squad over the hump.

WORST WITH A RING: Jon Gruden, Head Coach, Tampa Bay Buccaneers

Here is the most ridiculous one for last…

Jon Gruden did not join the Buccaneers. He was traded to the Buccaneers. Tampa gave up two first-round picks, two second-round picks, and 8 million in cash to get him from Oakland.

And what did Gruden do? He walked into a team that Tony Dungy had spent six years building… and he won the Super Bowl by beating his former team.

The “Gruden Bowl.” Super Bowl XXXVII. Buccaneers 48, Raiders 21. And here is the thing everyone forgets… Gruden knew all of Oakland’s plays. All their signals. All their audibles. He had just left that team. He had the ultimate inside information.

Not to mention that he did it as the youngest coach to win a Super Bowl at 39 years old until Sean McVay came along.

At the time, it felt like Gruden was primed to be anointed as one of the best coaches to ever do it… But it as it turns out, he might have just been in the right place at the right time.

But what happened after?

In six years post-Super Bowl with Tampa, Gruden made the playoffs exactly once. Never won another playoff game. 

The team Dungy built aged out, and Gruden could not adjust.

Then he came back to the Raiders in 2018 on a 100 million contract. 22 and 31 records before resigning amid a scandal in 2021.

When all was said and done, his career record was 117 and 112. Barely over .500… Not pretty.

Yes, Gruden has a Super Bowl ring. But he did not build that team… and he had the good fortune of going up against his former staff, who stunningly neglected to change up their signs and verbiage at all. 

No wonder his career numbers look more like a guy who got lucky once than a guy who figured out how to win. But is he coming back again? Who knows.