Picking the Chicago Bears’ biggest draft day regret is like selecting the worst bottom bracket team in the NCAA Basketball Tournament. There are so many possibilities how do you narrow it down to just one?

The Bears certainly regretted finishing 1-13 and tied for the worst record in the NFL with the Pittsburgh Steelers in 1969. In a coin flip to decide who would pick first in the draft the Steelers won and selected quarterback Terry Bradshaw. They went on to dominate football in the 1970’s.

The Bears decided to trade out of the first round. Their first pick in that draft came in the third round, No. 54 overall, wide receiver George Farmer. He played five undistinguished NFL seasons.

In all, from 1966 until 1975 when new general manager Jim Finks selected eventual Hall of Fame running back Walter Payton in the first round the Bears player personnel staff should have snuck out to take in a baseball game. They rarely picked a player that made an impact on the roster.

As bad as those days were, the worst was still ahead of them. Winning "Worst at Show" is the first Salaam runs against the Packersday of the 1995 NFL Draft. On April 22 the Bears selected Heisman Trophy winner Rashaan Salaam No. 22 overall and regretted it for years afterwards.

The Bears had made the playoffs in 1994 with a 9-7 record but were knocked out of the playoffs in the Division Round 44-15 by the 49ers after beating the Vikings in the Wild Card game. Even with a winning record though, the offense finished No. 24 out of 28 NFL teams in points scored. Their running game, led by Lewis Tillman, could only manage a 3.3 yards per carry average, No. 26 in the league.

Salaam had just finished smashing college football rushing records at the University of Colorado in 1994 with 2,055 rushing yards and 24 touchdowns. He dominated the Heisman Trophy voting and was universally projected to be a first round selection in the 1995 draft.

Four running backs came off the board before the Bears made their pick at No. 21. Ki-Jana Carter (second to Salaam in the Heisman voting) was first overall. In picks No. 17 to 19 Ty Wheatley went to the Giants, Napoleon Kaufman to the Raiders and James Stewart to the Jaguar.

After Salaam, in the second round they picked defensive end Pat Riley out of Miami (FL) and selected punter Todd Sauerbrun four picks later.

After holding out and missing most of training camp, Salaam rushed for 1,074 yards in the 1995 season and scored 10 touchdowns. He also, in a sign of troubles to come, fumbled nine times. After that his career flat-lined. He played two more seasons with the Bears and only gained 610 more yards. Two seasons later he ran once for 2 yards with the Browns. In 2001 he played in the XFL for the Memphis Maniax in 2001. In 2003 and 2004 Salaam tried again to mount a comeback but couldn’t make an NFL roster and found himself out of football.

As for the other two players selected on that first day, Pat Riley played one game in the NFL. Sauerbrun turned out to be flakier than a January Blizzard. He was never able to out-kick his on and off field problems and bounced around the NFL after spending four seasons with the Bears.

What drags this draft down to lowest of the low is they drafted three players and still missed highly regarded, though injury plagued at Pitt, running back Curtis Martin, elected to the Pro Football Hall of Fame in 2012. Terrell Davis could also be considered a miss in that draft but the entire league missed on him until the Broncos selected him in the sixth round. The Bears missed again on their fourth pick, washout guard Evan Pilgrim. Four picks later wide receiver Antonio Freeman slipped past them to the Packers.

Salaam’s failure hamstrung the Bears in the 1998 draft when they had the No. 5 pick in the first round. Consensus that year had the top five players set, just not the order of selection. The Bears joined the Chargers (Ryan Leaf) as draft losers when they picked running back Curtis Enis.

Enis was considered “can’t miss” with both power and speed when he came out of Penn State. The Bears received offers in exchange for their pick but they needed a quality running back on the roster and kept the pick.

Being in a position where they had to draft Enis cost them the opportunity to draft defensive end Curtis Enis RunningGrant Wistrom, Tackle Kyle Turley, linebackers Keith Brooking and Takeo Spikes or cornerback Samari Rolle, all long-time Pro Bowl players that were available to them.

In a 2012 interview with Fred Mitchell of the Chicago Tribune Salaam admitted that partying and marijuana use contributed to his failed career. “"I had no discipline. I had all the talent in the world. You know, great body, great genes. But I had no work ethic and I had no discipline.”

Of course, no list of Bears draft day regrets would be complete without mentioning quarterback Cade McNown in 1999. After quarterbacks Tim Couch, Donovan McNabb and Akili Smith went first, second and third the Bears traded picks with the Redskins. They went from No. 7 to 12 and lost out on the chance to select Daunte Culpepper instead of McNown. The Redskins used the Bears pick for cornerback Champ Bailey.

In 2005 they again struck out with a first round running back pick when they selected running back Cedric Benson with the fourth overall pick. The first problem was, they didn’t need him. The Bears already had a quality running back on the roster in Thomas Jones. Second, they passed on DeMarcus Ware, safety Antrel Rolle and a quarterback that the Packers took at No. 24 named Aaron Rodgers. The Bears wouldn’t have reached for Rodgers anyway. They had quarterback of the future Rex Grossman on the roster.

While the last two draft disasters are every bit as bad, Salaam’s failure forced the Bears into another draft dud three years later. That’s enough to make him the worst of a forgettable group.