Time and free agency had taken its toll on the team of the decade, and the Cowboys were desperately clinging to hopes that they could put together one more Superbowl run before closing the book on a Dynasty.
Offensively, the "triplets" were all in their thirties, but were still effective. The line still consisted of pro bowlers Larry Allen and Erik Williams, center Mark Stepnoski, and Flozell Adams who was entering his second season.
The Defense still had some big names of its own. The Cowboys defensive backfield of Deion Sanders, Kevin Smith, Darren Woodson, and George Teague was as good as any in football. Dallas also had solid linebackers in Randall Godfrey and Dexter Coakley.
Although they were aging, The Dallas Cowboys were still just a few pieces away from making a push at one last Superbowl before its core group of players' time had come and gone.
Due to free agent losses such as Alvin Harper and Jay Novachek the team's passing game was in dire need of another receiving threat to go along with Michael Irvin.
Unfortunately, the 1999 draft class wasn't exactly boasting the greatest receiving prospects of all time. The Cowboys held the 18th pick of the first round. Beyond Torry Holt, who ended up going sixth overall to the Rams, there wasn't another wideout that was projected to be able to provide the impact that the Cowboys were looking for.
So to address Troy Aikman's need for another legitimate target, Jerry Jones signed free agent "Rocket" Ismail just prior to the 1999 draft.
Rocket was coming off of a 1,000-plus yard, eight touchdown season with the Carolina Panthers. Still one of the fastest players in the entire league, Ismail would be able to stretch the field and provide a much needed deep threat for the Cowboys' offense.
So far so good.
I'd like to say that this is where the Cowboys went on to draft a ton of young talent that not only contributed to another Superbowl run, but also helped to solidify a foundation for the future. I'd love to go on and on about the diamonds in the rough Jones and Lacewell found.
I'd love to say that sound decisions were made that ensured the Cowboys would not return to a dreaded state of mediocrity. But the simple fact of the matter is that nothing could possibly be further from the truth.
With the 18th pick in the 1999 NFL Draft, the Dallas Cowboys select...Ebenezer Ekuban?
Another defensive end from UNC, the "Headless Horseman" started only 34 of his possible 80 games that resulted in 12.5 career sacks as a Cowboy. If Dallas had to go defensive end with this pick, Patrick Kerney, Mike Rucker, and Aaron Smith were three future pro bowlers who were still on the board.
With that first round selection in '99 draft the Dallas Cowboys began a run of the most embarrassing, ill advised, and destructive personnel moves that would hurt the team for years to come. In a three year span Jerry Jones, and Director of Scouting Larry Lacewell, pulled off three of the worst drafts in the history of the franchise.
The rest of the '99 Dallas Cowboy draft went like this...
Round 2: Solomon Page
Solomon was and offensive guard from West Virginia who started for parts of three seasons will the Cowboys. He was out of the league in less than four years.
Round 3: Dat Nguyen
The diminutive inside linebacker from Texas A&M was one of the few bright spots during this period. Nguyen eventually became a starter, but was plagued by injuries most of his career. He did manage to start for three entire seasons, and broke 100 tackles each time.
But now it REALLY gets bad...
Round 4: Wane McGarity
A wide receiver out of Texas, McGarity played in 22 of 35 possible games as a Cowboy with a whopping 39 catches and two touchdowns.
Round 6: Martay Jenkins
The Nebraska-Omaha wideout was cut from training camp. He played from 1999 to 2002 with the Arizona Cardinals. We didn't miss out on anything.
Round 7: Mike Lucky
This tight end out of Arizona was a Cowboy for all of three seasons. He had 19 catches and one touchdown in 46 games. And no, he was not a blocking tight end.
Fast forward a year to the 2000 Draft. This draft was doomed before it started. Following the loss of Michael Irvin to a career ending injury, the Cowboys thought it would be wise to give up two first round picks to sign Joey Galloway. A first rounder in 2000 and another in 2001.
Two first rounders were given up for a wide receiver that was basically a carbon copy of Rocket Ismail. Instead of replacing a possession receiver with a possession receiver, Jerry went and got another small burner.
The 2000 draft featured the following Cowboy greats: Dwayne Goodrich, Kareem Larrimore, Michael Wiley, Mario Edwards, and Orantes Grant.
The highlight of the 2001 NFL Draft came when Jerry Jones shocked the football world and picked Quincy Carter out of Georgia rounds before he was projected to be chosen. Yes, I said rounds, not picks.
With eight total picks in the 2001 draft Jones and Lacewell walked away with Willie Blade, Markus Steele, Matt Lehr, Daleroy Stewart, Colston Weatherington, John Nix, and Cha-Ron Dorsey, and the biggest shock of a quarterback that anyone could have imagined.
Three straight years of terrible drafting and personnel decisions had done their damage. The aging stars moved on without any young talent to replace the loss.
It has now been a decade since the draft of 1999. A draft that unfortunately laid the foundation for years of heartache for Cowboy fans. But only recently has the franchise been able to show signs of life again, teaching us all just how important this draft at the end of the month can be.
And this is one of the reasons that draft day is such a big deal in the NFL.