I completely disagree with this assessment of the 1999 season - in fact your reasoning has no merit what so ever.
First the players you named:
Kirkland only played one more season in Pittsburgh, and he was 28 years old.
Gildon was only 27 years old -- and would go to the Pro Bowl the next three consecutive years.
DeWayne Washington was 27 years old -- and didn't miss much time over the next few years he played in Pittsburgh
Chad Scott was only 25 years old and was in his 3rd season (in a way 2nd season as he had missed 199
Steed (30) and Oldham (31) --
1999 was their last year with the team!
Staat --- this is by far the oddest player you added...he was 23 years old in 1999, he was in only his 2nd season, and he was on the team only one more year.
And finally yes - Kordell Stewart, age 27 -- will people ever stop complaining about Kordell Stewart?? They tried to replace him several times -- they couldn't find anyone better (QB's were very hard to find in the late 90's) but he would still manage to go to the Pro Bowl 2 seasons later.
The 1999 team didn't suffer because of age to their "star" players -- and it didn't suffer because Cowher was too "buddy-buddy" with players (obviously as many of these players didn't stay long after 1999) --- or because Dan was too old --- there were a number of reasons.
Key problems were -
The loss of Dirt to injury,
Kevin Gilbride coming in as Offensive Coordinator -- and attempting to make Kordell something he wasn't.
Tom Donohue also was "let go" at the end of 1999 as Dir. of Football Operations.
And finally Troy Edwards was a 1st round bust -- he lasted only two more seasons in Pittsburgh --- and then we let him go.
A lack of cold blooded business was not in shortage at this time --- a lack of a star quality QB or a Coordinator who knew how to use Kordell was.
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