SAN FRANCISCO The Toronto Blue Jays had won the World Series a few months earlier, and were on their way to winning another when they drafted Chris Carpenter with the 15th overall pick in the 1993 draft.
Two years later, the Blue Jays held the No. 17 pick and went with a tireless and disciplined high school kid who had been one of Colorados best cross-country runners at Arvada West outside Denver: Roy Halladay.
Tim Wilken, the Cubs amateur scouting director, was involved in both of those selections, part of the 25 seasons he spent in the Toronto organization, which became a model for player development under Hall of Fame executive Pat Gillick.
If Carpenter hadnt signed with the Blue Jays, he was already committed to Creighton University to play for Jim Hendry, Wilkens childhood friend growing up in Florida and the future Cubs general manager.
This was a recruiter so aggressive and charming that they had a saying in Omaha, Neb., around the baseball offices: Jim Hendry could sell ice to the Eskimos and make them think they were getting a good deal.
Theyre all good baseball people, Carpenter said. They know what theyre doing.
Theo Epstein, Jed Hoyer and Jason McLeod are the new executives in charge at Clark and Addison, but the draft that begins Monday night will also be shaped by the scouts loyal to Wilken and Hendry, and they absolutely have to get it right.
Whether they wind up being frontline starters or late-inning relievers, the Cubs know they need more power arms.
Cubs fans and sometimes the people who draft them fall in love with prospects. But remember how long it took Halladay and Carpenter and even Jeff Samardzija to become difference-makers.
At the start of spring training, Samardzija turned around a question from a Boston reporter about what he knew of Epsteins Red Sox by saying: They have big shoes to fill after Jim left.
Samardzija still has the guts and the personality that made him a football star at the University of Notre Dame. At the age of 27, hes showing that the 10 million investment was worth it, pitching like a potential All-Star.
Samardzija (5-3, 3.09 ERA) laughed when a reporter mentioned that it seems like his perception has gone from being a total bust to the only untouchable player on the Cubs roster.
Its probably somewhere in the middle, Samardzija said. Thats the way it goes, especially with the media and things like that. Everything seems to have to be on the poles. Nothings ever really in the middle. Everything seems like its got to be a definitive: Hes terrible. Or a definitive: Hes gonna be great.
If you look at most cases, its somewhere in between that. A lot of it just has to do with development. Certain guys develop differently. Some guys want to develop. Some guys want to just stay the same.
I just knew that four or five years ago, I had a lot that I needed to improve on and I didnt really care what people were writing or what was being said. I just knew what I needed to (do).
Epstein, Hoyer and McLeod believe that keeping pitchers healthy is the next frontier, and that power arms show up more in the postseason. So they will pore over medical records and analyze video, to see which mechanics are cleaner and more likely to avoid a breakdown.
But Cubs scouts have also been challenged to get more information than the other area guy, to talk to more people around the school and establish a better relationship with the family, to find out what makes the player tick.
Carpenter graduated from Trinity High School in New Hampshire and made his big-league debut less than a month after his 22nd birthday.
But Carpenter didnt really start to put it all together until he was almost 30, while pitching for the St. Louis Cardinals. In 2005, he won the Cy Young Award and the first of his two World Series rings.
I dont know what separates you, Carpenter said. My goal was to try to make it to the major leagues. I did everything I could to make sure that when I was done, if I didnt make it, I knew I tried as hard as I could.
Halladay made his big-league debut at the age of 21, near the end of the 1998 season. But by 2001, he was busted back to Class-A Dunedin, restarting the climb that would help him win the Cy Young in both leagues.
Halladay didnt have his real breakthrough until the age of 25, winning 19 games and accounting for 239 13 innings, foreshadowing the Philadelphia Phillies ace that would become known as the best pitcher on the planet.
The Cubs will say the right things and feel great about their choices across the next three days. The challenge will be staying the course.
Thats just part of the game, Carpenter said. You always have to have patience, of course. Unfortunately, at some point in time, if theyre not doing what you think or what you projected, you have to move on.