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The Most Heartbreaking Cincinnati Bengals Moments

Updated June 14, 2019 1.2k votes 222 voters 9.1k views16 items

Over the course of 46 seasons in the NFL, the Cincinnati Bengals seem to have had more than their fair share of heartbreaking moments. We're partnering with the Cincinnati Enquirer to take a nostalgic look back at some of the toughest moments Bengals fans have had to endure through the years, from injuries to fumbles. What's the worst moment the Bengal fans have ever experienced?

We have 16 of the worst moments in Bengal history for you to relive, in no particular order. Take a look through and remember the pain of those days so you can finally let go and move forward to a brighter Bengal future. 

  • 1

    Bill Walsh Gets Passed Over for Head Coaching Job, Goes to San Francisco and Wins Super Bowl Against Bengals

    This is certainly one of those cases where hindsight is 20/20. Walsh served as an assistant under legendary Bengals coach Paul Brown, where he formulated what is now known as the West Coast Offense – an offensive scheme focused on short horizontal passes in hopes of stretching out an opposing defense. Following the 1975 season, Brown retired and named Bill "Tiger" Johnson as his successor. Walsh would later say that Brown, "worked against my candidacy," to be a head coach anywhere in the NFL. In 1979, he was named head coach of the San Francisco 49ers and drafted quarterback Joe Montana from Notre Dame in the third round. Walsh would win two of his three Super Bowls against the Bengals, first in 1981 and later in 1988 and would end up being considered one of the greatest coaches in NFL history.
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  • 2

    Joe Montana to John Taylor in Super Bowl 23

    Up 16-13 with 3:20 left in the fourth quarter, it looked like the Bengals were going to win their first Super Bowl title... but if they had, then this wouldn't be part of the Most Heartbreaking Bengals Moments. Quarterback Joe Montana led the 49ers on an 11-play, 92-yard drive for the winning score – a 10-yard touchdown pass to John Taylor with 36 seconds left in the game. This ended up being 49ers coach Bill Walsh's final game and his second Super Bowl win over the Bengals (the first was in 1981). To rub salt into the wound, in 2006, named this game the best Super Bowl game of all-time, although there have been some close ones since that list came out.
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  • 3

    2006 Series of Arrests

    The 2006 offseason was a memorable one for the Bengals, but not in a good way. Nine players were arrested and/or suspended for their actions off the field. While a few of them were for DUI and drug charges, there was also Frostee Rucker's two counts of spousal abuse, A.J. Nicholson's burglary charge, and Matthias Askew being tased for refusing to move his illegally-parked car. The most prominent infractions, though, came from wide receiver Chris Henry, who was involved in four separate incidents, including speeding and DUI, marijuana charges, providing liquor to minors, and pulling a gun on a group of people in Orlando. The Bengals finished the season 8-8 and missed the postseason, a drop-off from their 11-5 finish the year before.
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  • 4

    Stanley Wilson Pre-Super Bowl Cocaine Relapse

    As a fullback for the Bengals, Wilson was suspended twice for cocaine use and was forced to sit out the entire 1985 and 1987 seasons. His most notorious infraction came two years later in 1989, on the eve of Super Bowl 23. Wilson told several teammates that he needed to get his playbook before their last meeting prior to the game. Twenty minutes later, his position coach, Jim Anderson, found him in the bathroom in the midst of a cocaine high. The Bengals left him off the roster for the game, which the San Francisco 49ers won 20-16. With the incident being his third infraction, he was subsequently banned from the NFL for life.
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