Worst moments in Cincinnati Bengals history

What are the worst moments for each NFL franchise? Yahoo Sports provides our opinion, which you are free to disagree with (and we’re sure you will).

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5. Paul Brown snubs Bill Walsh to be his successor

Pro football might not exist in Cincinnati were it not for Paul Brown, but one of the city’s most interesting parlor games is imagining what would’ve happened had Brown hired Walsh to succeed him in 1975. Walsh, who served as Brown’s offensive coordinator, was famously passed over for Bill “Tiger” Johnson, a snub that caused Walsh to resign. Walsh later claimed that Brown gave him subpar reviews in his search for a head coaching job and boy, did he ever get his revenge, beating the Bengals in not one, but two Super Bowls. The course of NFL history would have obviously been changed had Brown recognized the genius he had in his midst, so what’s different? Well, the “West Coast” offense would have a different name, the 49ers wouldn’t be among the league’s most decorated franchises and there’s a good chance that Jerry Rice might’ve worn tiger stripes, being selected just two picks after the Bengals turn in the 1985 NFL draft. Oh, and the Bengals might have a couple of Lombardi Trophies in their awards case. Small details, really.

4. Jeremy Hill fumbles away a Bengals playoff win

Vontaze Burfict intercepted a Landry Jones pass with 1:36 remaining and there seemed to be no way the Bengals could mess this one up. The team was leading the Steelers by one point in a January 2016 AFC wild card game and looking at ending a seven-game playoff losing streak with its first playoff win since 1990. But these are the Bengals we’re talking about. With the team owning a 95.9 percent win probability, Hill somehow fumbled on the first play from scrimmage and the Steelers recovered. It was then the Bengals really got their Bengal on. With Ben Roethlisberger back in the game, both Burfict and Adam “Pacman” Jones were hit with 15-yard penalties, allowing the Steelers to get into range for a game-winning field goal. The kick was good and the Bengals found themselves in a familiar position, knocked out of the wild card round for the fifth straight season.

3. Stanley Wilson’s cocaine binge

The Brown family has a reputation for giving multiple chances to players with character questions. That approach has come back to bite them many times, but never on a bigger stage than the night before Super Bowl XXIII in Miami. That’s when fullback Stanley Wilson, who had already missed two entire seasons for violating the league’s substance abuse policies, suffered a relapse and went on a cocaine binge in his hotel room. “Sam [Wyche] sent Jim Anderson and I think Bill Connelly, the trainer at that time, up to Stanley’s room and they found him in the bathtub naked, coked out of his mind,” Bengals offensive coordinator Bruce Coslet told the Cincinnati Enquirer. “So they got him dressed, called the paramedics, we’re taking him to the hospital, and he ran away. He literally ran down the steps of the hotel and gone before he got in the ambulance. I never saw him again. They didn’t find him for three or four days, I guess.” With Joe Robbie Stadium a muddy mess, there are many Bengals who believe Wilson’s presence would’ve made a huge difference in the team’s 20-16 loss to the 49ers.

2. Carson Palmer shreds knee in playoff game

After a decade-and-a-half filled with largely unwatchable football, the 2005 Bengals were a revelation. Carson Palmer had a breakout season, as the Bengals went 11-5 to earn their first playoff berth since 1990. The city was delirious over a possible playoff run if they could get by the rival Steelers, but it didn’t take long for disaster to strike. In fact, it’s possible no playoff team has ever taken a quicker nosedive, and Bengals fans knew right away what they were seeing. After dropping back for his first pass of the game, Palmer was hit in the knee by a rolling Kimo von Oelhoffen, a former Bengal turned Steelers lineman. Though unintentional, von Oelhoffen effectively destroyed the Bengals’ season. Palmer tore both his ACL and MCL on the play, which turned out to be a 66-yard completion to Chris Henry. Making matters worse, Henry also suffered a season-ending injury on the same play. Though the Bengals would take an early lead, both losses were too much to overcome. Pittsburgh won the game 31-17 en route to a Super Bowl championship, while the Bengals saw another year added to a playoff winless streak that is currently at 27 years and counting.

1. Lewis Billups drops an interception from Joe Montana in Super Bowl XXIII

You thought this was going to be Montana-to-Taylor, didn’t you? There’s no doubt that play is the No. 1 heartbreaker, but Bengals fans contend the ultimate what-might-have-been moment came earlier in the fourth quarter. To set the scene: The Bengals led 13-6 after Stanford Jennings’ 93-yard kickoff return touchdown, but Joe Montana and the 49ers were on the move. The drive might’ve ended when Billups stepped in front of a Montana pass to the end zone that was intended for John Taylor. Though Billups couldn’t have been in better position – he should’ve been able to corral the ball easily – he muffed the play and the ball fell incomplete. Unshaken, Montana found Jerry Rice for a touchdown on the very next play and the 49ers comeback was on. San Francisco would win the game 20-16, while Billups’ name would forever be associated with missing out on an opportunity to put the Bengals firmly in control of a possible Super Bowl victory.