By Darin On April 17, 1999, the NFL Draft was held. University of Kentucky quarterback Tim Couch was the first pick by the expansion Cleveland Browns franchise. There were some pretty nice picks made too, as Couch was followed by Syracuse’s Donovan McNabb to the Eagles, Cincy taking Akili Smith of Oregon, Hall of Fame back Edgerrin James went 4th to the Colts, followed by Ricky Williams to New Orleans in the big trade by then coach Mike Ditka, basically giving all of his 1999 picks for the opportunity to draft Williams. NC State Wideout Tory Holt went next to the St. Louis Rams, and Hall of Fame Defensive Back Champ Bailey was picked up by Washington, according to Pro Football Reference.com.
The 1999 NFL Draft, held on April 17th, wasn’t just another weekend of scouting reports and podium handshakes. It remains one of the most fascinating “what if” chapters in football history—a day defined by a historic run on quarterbacks, a legendary trade that defied logic, and a reminder that talent evaluation is anything but a certain science.
The Year of the Quarterback
The headlines heading into the 1999 draft were dominated by a desperate need for franchise signal-callers. For only the second time in the common draft era, the first three picks were all quarterbacks:
- Tim Couch (Browns)
- Donovan McNabb (Eagles)
- Akili Smith (Bengals)
This “Big Three” set the tone for a draft where five quarterbacks were taken in the first 12 picks (including Daunte Culpepper and Cade McNown). While McNabb went on to have a Hall-of-Fame caliber career in Philadelphia, the struggles of Couch and Smith became cautionary tales about the risks of drafting for need over value.
The Ditka Gamble
Perhaps the most enduring memory of April 17, 1999, was Mike Ditka’s unprecedented gamble. The New Orleans Saints head coach was so enamored with Texas running back Ricky Williams that he traded his entire 1999 draft class—plus first and third-rounders in 2000—to move up to the fifth spot.
It was a “win-now” move that ultimately backfired. While Williams was a productive player, the sheer loss of draft capital crippled the Saints’ depth for years, leading to Ditka’s firing shortly after. It remains the gold standard for “overpaying” in draft lore.
Hidden Gems and Lasting Legacies
Beyond the chaos of the first round, 1999 proved that the best value often hides in the shadows. Champ Bailey (7th overall) became one of the greatest cornerbacks to ever play the game, but the real steals happened later. The Green Bay Packers found receiver Donald Driver in the 7th round, and the Indianapolis Colts snagged Edgerrin James 4th overall, choosing him over the more hyped Ricky Williams—a move that eventually helped secure a Super Bowl.
Decades later, the 1999 Draft stands as a masterclass in the NFL’s volatility. It reminds us that whether you’re trading away your entire future or betting the house on a franchise QB, the draft is the league’s ultimate high-stakes poker game.
Selections taken in the 1999 NFL Draft
Special thanks to Pro-Football-Reference.com
