Cincinnati Bengals Hall of Shame: Worst breakup and more

After celebrating the Bengals by highlighting their players who someday could be enshrined in the Pro Football Hall of Fame, we flip the script to give you Cincinnati's Hall of Shame.

Worst breakup: QB Carson Palmer

Palmer had a successful NFL career that began as the Bengals' No. 1 overall pick in the 2003 NFL Draft. He was selected to three Pro Bowls and finished his career with a winning record (92-88-1).

In 2005, Palmer signed a lucrative nine-year contract extension with the Bengals. But after Cincinnati went 4-12 in 2010, ESPN reported that Palmer planned to request a trade.

Owner Mike Brown was not pleased, stating, "If he is going to walk away from his commitment, we aren’t going to reward him for doing it."

Palmer did not report to training camp in 2011 following the Bengals' selection of QB Andy Dalton in the 2011 NFL Draft. Cincinnati placed Palmer on the reserve/did not report list and Brown wished him well in retirement. However, after never officially filing for retirement, Palmer was later traded to the Raiders.

Worst draft pick: QB Akili Smith

Smith declared for the 1999 NFL Draft after two semi-successful seasons at Oregon (56.6% completion percentage, 5,148 yards passing.) The Bengals figured he could be a franchise QB and drafted him with the No. 3 overall pick.

Smith, however, got off to a rocky start with the Bengals, holding out in a contract dispute and missing most of training camp. As a rookie, he threw for 2,058 yards, five touchdowns and 12 interceptions, and the team benched him during his second season. After the 2001 season, Smith never again played in the NFL.

To make matters worse for Cincinnati, the next four picks after Smith in the 1999 draft were RB Edgerrin James, RB Ricky Williams, WR Torry Holt and CB Champ Bailey. All became stars.

Worst free agent: WR Antonio Bryant

The Bengals signed Bryant to a four-year, $27 million contract in 2010 after he posted two 1,000-yard receiving seasons in three years. Bryant's best season came in 2008, when he had 83 catches for 1,248 yards and seven touchdowns for Tampa Bay, but Cincinnati should have seen the red flags that started popping up the following season.

In 2009, Bryant was limited by a left knee injury that eventually required surgery. He only practiced once and was released prior to Week 1, never playing a down, but he collected $8 million in guaranteed money from Cincinnati.

Worst loss: Super Bowl XXIII on Jan. 22, 1989

In 1988, Cincinnati was a powerhouse as the No. 1 seed in the AFC, finishing 12-4 in the regular season. The Bengals were just 39 seconds away from their first Super Bowl victory in franchise history. But then QB Joe Montana hit WR John Taylor in the back of the end zone for a touchdown, sealing the game for San Francisco, 20-16.

The 49ers had outplayed Cincinnati for most of the game, totaling 452 yards to the Bengals' 229 yards. 

Cincinnati would not return to the Super Bowl again until the 2021 season.