ESPN MLB Playoffs 2008

ST. PETERSBURG, Fla. -- In June 1999, the Tampa Bay Devil Rays selected outfielder Carl Crawford in the second round of the Major League Baseball draft. That same summer, a young Tulane University graduate named Andrew Friedman went to work as an analyst for the investment banking firm Bear Stearns in New York.

Nine years later, the principals are trending upward. The Rays, minus the "Devil," are preparing for their World Series debut. Crawford, a two-time All-Star, is the starting left fielder and longest-tenured player on the roster. And Friedman, a boyish-looking 31, is the front-runner for baseball's Executive of the Year award.

The only loser in this story is Bear Stearns, which was sold to JPMorgan Chase for a bargain price in March as a casualty of the subprime mortgage crisis.

"It's a little surreal," Friedman said from the home clubhouse at Tropicana Field on Monday. "I think it will be after our last game before I can gain full perspective and take a moment to reflect on this season. Being mired in the middle of it, it's very difficult right now."

In an age of instant gratification, the Rays stand as a paragon of long-range thinking and making do with limited means. They won 97 games this year and captured the American League East title despite baseball's 29th highest payroll. Tampa Bay sported a $43 million payroll on Opening Day, while New York, Boston, Toronto and Baltimore invested about $508 million combined in player salaries.

The Rays' home park, Tropicana Field, is generally regarded as substandard. They have the second smallest season-ticket base in the game, and nobody knows if they'll eventually land in the new ballpark they so greatly desire. As principal owner Stuart Sternberg likes to say, "We're in the baseball business, not the stadium-building business."

But say this for the Rays: They've made the most of a decade worth of suffering.

Like their World Series counterparts, the Phillies, the Rays have mined a mother lode of talent through the draft. Of the 25 players on Tampa Bay's American League Championship Series roster, only eight were signed and developed from within. But they were all significant contributors.

The list includes former first-round picks B.J. Upton, Rocco Baldelli, Evan Longoria and David Price, all of whom were chosen among the first six picks because the Rays had finished so low in the standings. But Tampa's draft hauls also included such hidden gems as pitchers James Shields (16th round) and Andy Sonnanstine (13th round).

Crawford, Baldelli, Upton and Shields were all selected by Dan Jennings, Tampa Bay's former scouting director, who has since moved on to a position as assistant general manager in Florida. And they all fit Jennings' core philosophy, which was to disdain "safe" picks for players with higher ceilings.

"The organization gave us a clean canvas and a chance to paint, and we poured everything we had into it," Jennings said in a phone interview. "We always looked for athletic players who were more high-risk, high-reward. We always tried to stay away from what they call 'cute little players' and go for impact guys."

Or as Tampa Bay's current scouting director, R.J. Harrison, once said of Jennings, he "swings for the fences every round."

Crawford was so athletic, he was offered a football scholarship from Nebraska and could have played basketball at UCLA if he hadn't opted for baseball. Baldelli displayed all the requisite skills as a high schooler in Rhode Island, but he tore an oblique muscle and played in only a handful of games his senior year before the Rays waded in with a $2.25 million bonus.

Upton, a wondrous mix of power and speed, fell into Tampa Bay's lap when Pittsburgh spent the first pick on Ball State pitcher Bryan Bullington, a quintessential "signability" choice who is still looking for his first big league win.

"Every night during the spring of 2002, I went to bed praying to the baseball gods that Pittsburgh would take someone else and let B.J. come to us," Jennings said.

And just think: The Rays used the top overall pick in 1999 on outfielder Josh Hamilton, whose time in Tampa Bay finally ran out after a harrowing ordeal filled with drug and alcohol abuse. Just imagine how he'd look in manager Joe Maddon's lineup. The Rays also gave serious thought to drafting Mark Teixeira in 2001 before signability concerns prompted them to go with pitcher Dewon Brazelton.

From the moment Tampa Bay was awarded an expansion franchise, this was the route the Rays planned to take. Chuck LaMar, Tampa Bay's first general manager, vowed to stress scouting, player development and patience over knee-jerk thinking. But when Tampa Bay's expansion cousins, the Arizona Diamondbacks, achieved some success with Jay Bell, Matt Williams and other veteran players, Rays ownership pushed for a more aggressive approach to rekindle that old honeymoon feeling with fans.

The result: The Jose Canseco-Greg Vaughn-Fred McGriff-Vinny Castilla "Hit Show" fiasco, and some disastrous free agent signings by LaMar. They don't come much worse than pitcher Juan Guzman, who gave the organization 1 2/3 innings after signing a two-year, $12 million deal.

Friedman, in contrast, has shown a flair for free agent steals and productive, under-the-radar trades. Consider first baseman Carlos Pena, who signed with Tampa Bay as a minor league free agent in January 2007. Pena hit 46 home runs in his first year with the club, and parlayed it into a three-year, $24 million extension.

"As a small-revenue team, we don't have the luxury of one-dimensional players," Friedman said. "We always liked Carlos as a hitter and what he brings defensively, so we felt like he was worth a shot. That's one of the benefits of not being very good at the time: You're able to give chances to players when you like their profile."

On the trade market, Friedman acquired reliever J.P. Howell from Kansas City for Joey Gathright, picked up Willy Aybar from Atlanta for pitcher Jeff Ridgway, added reliever Dan Wheeler from Houston for Ty Wigginton, and brought in Edwin Jackson from the Dodgers in a deal for Danys Baez and Lance Carter.

Friedman's big impact deal came last winter, when he sent outfielder Delmon Young to the Twins for pitcher Matt Garza and shortstop Jason Bartlett. The Rays had a surplus of position players, the Twins were in position to move some pitching, and the move was right in line with Friedman's desire to upgrade the defense and the rotation.

Mission accomplished. Bartlett gave the Rays' some needed infield glue, and Garza went 11-9 before winning the ALCS Most Valuable Player award.

Garza, truth be told, wasn't thrilled when he received word that he'd been dealt from Minnesota to Tampa Bay. But it didn't take him long to come around.

"I was disappointed for about three to five minutes until I got on the phone with Andrew Friedman," Garza said. "He was so energetic and excited to get me and bring me in, and that made me feel right at home."

Friedman's biggest strengths, according to those who've worked closely with him, are his ability to listen and incorporate the opinions of others. Former Houston general manager Gerry Hunsicker, for example, has played an important role as an adviser and experienced sounding board in Tampa. Friedman is also progressive enough to have a healthy respect for statistical analysis and the opinions of the scouts.

"Andrew is an opportunist," said Rays president Matt Silverman. "He's always looking to make improvements within the club. Some are major leaps and require risk, and others are things on the margin. Oftentimes, it's those decisions that make the difference in the end."

The Rays haven't quite reached the end, but the run up to it sure has been fun. They've outlasted the American League East, the White Sox and the Red Sox, and now they've officially emerged as ready-for-prime-time players. It's the beginning of a bull market for baseball in Tampa Bay.

Jerry Crasnick covers baseball for ESPN.com. His book "License To Deal" was published by Rodale. Click here to order a copy. Jerry can be reached via e-mail.