The 1990's

Year Coach W L T PCT
 
Totals  
75 85 0 .469
1990 Mike Ditka 11 5 0 .688
1991 Mike Ditka 11 5 0 .688
1992 Mike Ditka 5 11 0 .313
1993 Dave Wannstedt 7 9 0 .438
1994 Dave Wannstedt 9 7 0 .563
1995 Dave Wannstedt 9 7 0 .563
1996 Dave Wannstedt 9 7 0 .563
1997 Dave Wannstedt 4 12 0 .250
1998 Dave Wannstedt 4 12 0 .250
1999 Dick Jauron 6 10 0 .375

The 1990s marked the official end of the George Halas era in Chicago. The Bears made the playoffs three times. Twice under Ditka's direction (90 and 91) and once under Michael McCaskey's hand picked coach Dave Wannstedt (94). Michael McCaskey refreshed from a ski-trip vacation, fired Mike Ditka after Da Coach twisted in the proverbial wind while McCaskey rode the ski-lift. The All McCaskey era began officially in 1993 when former Dallas Cowboys Defensive Coordinator was hired as Head Coach/GM.

Wannstedt led the Bears to the post-season once in his 6-year tenure. With many of the 80s players leaving via free angency or retirement, the McCaskey/Wannstedt re-stocked plan was a miserable failure. The Bears once regarded as fielding some of the best players did not have one player tagged as a Pro-Bowler for five consecutive season (1994-1998). Terrible drafts and bad free agent acquisitions, spiraled the Bears into unprecedented lows. The Monsters of the Midway existed in name only because the Wannstedt teams hardly represented anything fierce.

Also significant in the 1990s was the public display of ineptitude by Bears President Michael McCaskey. Besides his non-existent football sense in drafting, player evaluations, and the new salary cap economic knowledge, Mr. McCaskey further alienated fans and the city of Chicago's government with hollow threat to move the team out of the city. The tactic was to secure a new stadium for the Bears. Comically, the threat of the Gary Bears or Arlington Heights Bears did nothing to promote talks or phase Chicago officials. However, that failure coupled with Mr. McCaskey's horribly botched coaching hire in 1999 (Dave McGinnis for Dick Jauron) forced his mother Virginia Halas-McCaskey to fire her oldest son as team president.

Michael was replaced by long-time family friend and employee Ted Phillips whom promptly got a stadium deal done with the city of Chicago to refurbish Solider Field. To be fair, Michael McCaskey wasn't technically fired, but rather "promoted" to team chairman: A ceremonial role at best.

The All McCaskey 1990s (more specifically 1993-present) is a case study in organizational collapse.

Playoff Appearances/Championships

Year Record Summary
1990 11-5-0 The Bear final division crown until 2001 offered some promise as the Bears beat the re-built New Orleans Saints 16-6. A Saints team that ironically was turned around by former Bears GM Jim Finks. The win over the Saints send the Bears to New York to face the Giants who ended the Bears season with a 31-3 beat down.
1991 11-5-0 Mike Ditka's last playoff appearance was with this wildcard team who finished second in the division to the Detroit Lions. The Bears had hosted the wildcard game against the Dallas Cowboys. Dallas came into Chicago and handed "Iron" Mike a heart-breaking 17-13 loss. The following season would be Ditka's last on the Chicago sideline and be replaced by the Cowboys Defensive Coordinator Dave Wannstedt.
1994 9-7-0 Dave Wannstedt's second year proved to be his best as he led the Bears to the playoffs in the competitive NFC Central and securing a wild-card spot. The opening playoff tilt was against the division champs: Minnesota Vikings. The Bears went up the the Metrodome and beat the Vikings 35-18. The win earned them the right to face the San Francisco 49ers who easily soundly beat the Bears 44-15. This game was the last playoff appearance the Chicago Bears would have in the 90s.

All-Pros for the decade

Bears Pro-Bowler Pos Year
Neal Anderson RB 1990, 1991
Mark Bortz OL 1990
Mark Carrier DB 1990, 1991, 1993
Richard Dent DL 1990, 1993
Shaun Gayle DB 1991
Glyn Milburn KR 1999
Jay Hilgenberg OL 1990, 1991
Mike Singletary LB 1990, 1991, 1992
Donnell Woolford DB 1993