WORST QUARTERBACK: Steve Pelluer (he once called THREE timeouts in the first quarter of a game) It was too bad that Danny White was so injury prone late in his career. With him, it seemed like the Cowboys were never out of the game. Sounds funny but it's TRUE. And when he went down, everyone saw what we were left with. After a 6-2 start with Danny White in 1986, White went down against the Giants in week 9 with a broken wrist (phil pozderak and that patchwork offensive line didn't block LB Carl Banks) Enter Pelluer, and the Boy's staggered home 2-6 in the second half of the year, missing the playoffs, and snapping the record of TWENTY straight winning seasons, still an NFL record today, not likely to ever be surpassed.
Honorable Mention: Gary Hogeboom. One of the biggest mistakes if not THE biggest mistake by Coach Tom Landry. After the Cowboys lost three straight NFC Championship games in 1980-82, and then lost a disheartening home playoff game to the Rams in '83, many Dallas fans were fed up with Danny White, blaming him for the failure to get them to the Super Bowl. The following spring, (1984) according to Roger Staubach, there was a fan poll being conducted in the Dallas Morning News on the so-called QB controversy between Danny White and Gary Hogeboom. Many frustrated fans wanted to see what Hogeboom could do as the starter, thus the vote for him was higher and Landry actually went along with it. It was a decision that he shouldn't have made, and at the midseason, with the Cowboys at 4-3 and down 27-6 to the Saints, Tom Landry finally put Danny White back in and he led the Cowboys all the way back to a 30-27 win in overtime, and was back as the Cowboys starter the rest of the year. However, the so-called QB controversy had divided the team, as they finish at 9-7 and miss the playoffs for only the second time in twenty years. Hogeboom was traded to Indianapolis in 1986, after backing up White again in 1985 (Landry's final playoff year, and effectively the last hurrah of the Tex Schramm/Gil Brandt/Landry Cowboys)
WORST LUCK IN THE UNIVERSE AT OFFENSIVE LINE: Phil Pozderek. Always called for holding at the most inopportune times.
WORST COACH: Hate to say this, because the guy's a great assistant, just not head coaching material. The nod goes to Dave Campo, who never had a chance really. From 2000-2002, the Cowboys hit the skids after the glory days of the 1990's closed. They went 15-33 (three consecutive 5-11 seasons) He didn't have a chance really because the team was strapped in the Salary Cap department with dead money owed to Michael Irvin and Troy Aikman namely, who both had to retire a few years premature (before their contracts expired) because of a neck injury and concussions respectively. And they were still paying a hunk of change to past his prime Emmitt Smith. There was no cap money available during the Campo era to bring in impact players or make quality trades, forcing the team to hit rock bottom before finally being able to rise again.
Jerry Jones' ego getting in the way of Jimmy Johnson. It's fair to say that Jimmy Johnson had a huge Texas sized ego as well. If Jerry Jones wanted to keep winning, he should have given Jimmy what he wanted and let the man coach. This team could have won seven Super Bowls in the '90's But the clash of the JJ's led to Jimmy's stunning abrupt departure after leading the Cowboys to their second straight Super Bowl
Honorable mention: Jerry Jones firing Chan Gailey after he led the Cowboys to consecutive playoff appearances in 1998-99, winning the division in 1998. Granted, the Cowboys were in decline, but if you don't have someone better in mind to replace Gailey, then why fire the guy after he at least took you to the playoffs both years? They did win more than they lost with Gailey, something that they wouldn't be able to say for awhile after that.
SOME OTHER THINGS THAT WERE NOT COOL:
For a lot of the glory Landry years, Tex Schramm became known around the league as a cheapskate hoser when it came to paying his players. (Schramm wasn't actually the owner of the team, it just seemed like it) Another stupid and embarrassing thing Schramm did was in 1987 during the player's strike when he strong armed many of his stars into playing into the replacement games by inserting clauses in their contracts. If these players didn't cross the line and play with the "scabs" they all stood to lose many million in annuities. Players like Randy White, Too Tall Jones, and Tony Dorsett, and many others. They Cowboys became a marked team around the league because of it causing CB Everson Walls to say "People used to hate us out of respect. Now they hate us out of disrespect"
Also infamous was in the late 1990's when many of the Cowboys from the Glory run of 1992-96 were still on the roster and the team became embarrassingly refered to as the "Crack Wagon". Several players as we know, got involved in activities where they were in the wrong place at the wrong time, namely where there were drugs. An embarrassing and ugly final chapter to the team of the 90's.