2. Cade McNown
Who could possibly forget Cade McNown? The easy answer is: Bears fans have been trying to forget about this guy for years, now. But, he's too unforgettable. Chicago selected McNown 12th overall back in the 1999 NFL Draft, and his career in Chicago would last two short, hilariously poor years. That's it.
Going from a first-round draft pick out of UCLA to out of the league in just four seasons; yep, that's Cade McNown's story. He never played a regular season game for either the Miami Dolphins or San Francisco 49ers, the two teams he spent time with after the Bears.
The guy didn't even start a full season, or anywhere close to it. In his rookie year, McNown went 2-4 as a starter. In his second season, he went just 1-6. That entire two seasons felt like a lifetime for Bears fans, who had to suffer with injuries, suspensions and downright poor play from a myriad of quarterbacks including McNown, Jim Miller and Shane Matthews.
Looking back, the Bears could have drafted guys like Jevon Kearse, Damien Woody, or even Antoine W/infield in the first round if they hadn't gone with McNown. Heck, there were several other guys just in that first round alone who would have been worth the pick. But instead, the Bears went the classic bust route.