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Bad drafting has led the Chicago Bears to only five playoffs in the last 22 years

Former Chicago Bears first round draft pick Gabe Carimi was released by the Tampa Bay Buccaneers yesterday. His career hasn't lived up to his 1st round status, but was he the biggest flop in Chicago drafting history?

Kim Klement-USA TODAY Sports

We seem to ask this question every year or so. Every time a recent draft pick stinks, we wonder if he was the worst draft pick ever for the Bears.

Some bust out because of an initial overrating of talent, some due to an injury, some because of off field troubles, and some hit the trifecta of craptitude.

Offensive lineman Gabe Carimi is the latest failed Chicago Bears draft pick in the news. He was the 29th overall draft pick by then general manager Jerry Angelo, and most were on board with the selection. If you recall, there was a potential trade scenario between the Bears and the Baltimore Ravens that fell through as Carimi started to fall in the draft.

Hindsight tells us that Angelo should have allowed him to continue his descent.

The very next pick was defensive lineman Muhammad Wilkerson to the New York Jets. He was just named a 2013 All Pro. After that was d-lineman Cameron Heyward to the Pittsburgh Steelers, who just racked up 5 sacks and 7 passes defended in 13 starts. How would either of those two players look in Navy and Orange today?

But the Bears were looking to bolster their offensive line, and the next o-lineman went at #30 to the Green Bay Packers. Derek Sherrod has struggled with his own injuries, and he's yet to start an NFL game.

The NFL Draft is often times a roll of the dice, the Bears pick a bust at 29, followed by an All Pro, then a serviceable starter, sandwiched with another bust.

The Bears did flip Gabe Carimi for a 6th round draft pick in this years draft, so there's still hope to pull some value out of his first round selection.

Carimi wasn't Jerry Angelo's only bad #1 pick. Mark Columbo didn't work out with the Bears after being #29 overall in 2002. In 2003 Michael Haynes proved not to be a very good football player after going 14th overall. Cedirc Benson was 4th overall in 2005 and it seemed like his heart was never in it. Chris Williams washed out of Chicago after being taken 14th overall in 2008.

It wasn't only the first round that Angelo found some turds. Mark Bradley was 39th overall in 2005, Dan Bauzin was the 62nd overall pick in 2007, and Jarron Gilbert was 68 overall in 2009. A slew of busts helped lead to Angelo's firing, but the Bears were making poor decisions in the draft well before Angelo was hired.

Bad drafting is a big reason the Bears have only had five playoff appearances in the last 22 years.

Current GM Phil Emery has his own could-be-bust in defensive end turned linebacker Shea McClellin. If McClellin, the 19th overall pick, can't transition to the strong side linebacker spot, I see no reason why the Bears should keep him around.

Emery's second draft looks to be much better than his first and it's far too early to call his drafting record into question. We'll have early coverage of his third draft class in about three months.

Gabe Carimi could still end up playing somewhere in 2014. When Lovie Smith and the Tampa Bay Buccaneers cut him, it was as much a cost cutting move as it was performance based. But even if he finds a new home, it still doesn't change the fact that his time as a Bear was a failure.

There are plenty of recent flops for Bears fans to pick from, but who do you think is the most disappointing pick in recent memory?