The Rays had two picks in the first five rounds of the 2000 draft. This after finishing with 69 wins in 1999. With the sixth overall pick, the Rays grabbed Rocco Baldelli and when their next pick came (number 136) they selected Jace Brewer. The second, third, and fourth round picks were given up as compensation. To summarize:
Pick 46 to the Reds for Juan Guzman. They would pick Dane Sardinha. Xavier Nady is the only notable pick that came immediately after, and nobody before is worth discussion.
Pick 76 to the Cubs for Steve Trachsel. Nic Jackson was the pick, Grady Sizemore went at pick 75, and Nook Logan at pick 78. Giant Chris Young went later in the round.
Pick 106 to the Braves for Gerald Williams. Zach Miner was nabbed, the three picks before Miner were Todd Wellemeyer, David DeJesus, and Cliff Lee, meanwhile the three after: Cory Vance, Mark Woodyard, and Mewelde Moore. Yes, the most notable player that followed Miner is known for his football career, not his baseball doings.
How did those three players contribute? Well Guzman pitched one and two-thirds innings for the Rays before his arm exploded, so that's no good. Trachsel hung around for nearly 140 innings and finished his season with a FIP of 4.92. The Rays would package Trachsel for Brent Abernathy, so there is that. Williams once attempted to hit Pedro Martinez and -- like most of his at-bats -- missed wildly.
All together the Rays paid three draft picks and 20 million dollars, in return they received Brent Abernathy and some negative performance value to show for it. The worst part is this is hardly thinking in hindsight. None of those moves were all too intelligent at the time, yet the old Rays management completed them anyways. Giving up the chance to acquire young talent in place of mediocre old talent is just another data point on the record of idiocy.
Making reason of the old Rays mistakes is like trying to understand the Julio-Claudian family. In the end, they're still freaking insane.