Andre Pichette, Associated Press Matt Guerrier: From unprotected Pirates prospect to a spot on the staff of the American League Central Division champions. Click photo for larger image.

It was late fall of 2003 and Pirates general manager Dave Littlefield and his staff were tinkering with the team's 40-man roster for the upcoming Rule 5 draft and for the season to come. It's a rite of November that teams sit down to determine the 40 players they will protect. Those left off, if they have enough minor-league experience, are eligible to be selected by other teams in the Rule 5 draft.

The decisions that came out of those meetings seemed peculiar at the time. About 18 months later those same moves look to be outrageous miscalculations that cast doubt on Littlefield and his staff at least as talent evaluators and possibly as stewards of the franchise.

Errors in judgment occur from time to time in any major-league organization. Talent evaluation is not an exact science. But what transpired in November and December 2003 could impact the franchise for years. In those dark days the Pirates unaccountably left five players unprotected that other teams selected. Two seasons later all of those players are prospering. Two are in the majors, three will be there, if not this year, then next. Several have considerable upside.

Of most significance, all could be used by the Pirates.

In November 2003, the Pirates removed from their 40-man roster three players -- first baseman Walter Young, who had been the organization's minor-league player of the year in 2002, and pitchers Duaner Sanchez and Matt Guerrier. A player taken off the 40-man roster must be put on waivers. All were plucked by other teams.

At the same time the Pirates left unprotected enough good players that five of their prospects were taken in the Rule 5 draft the next month. Included among them were first baseman/catcher Chris Shelton and pitcher Jeff Bennett. Shelton was left unprotected despite the fact Brian Graham, the team's director of player development, called him the organization's best hitting prospect.

All of these players, who the Pirates believed not good enough to be on their lowly 40-man roster in 2004, are good enough to be on the 40-man rosters of better teams in 2005.

Young is a giant of a man at 6 feet 5 and close to 300 pounds. Many baseball people believe he's too big to succeed in the majors. He is, however, making believers in Baltimore. He hit 33 home runs for Class AA Bowie last year, a team record. He's with Class AAA Ottawa this season. Going into the weekend, he was batting .500 (24 for 48) and leading the International League. Young has his shortcomings. He's so big he might only be able to make it as a designated hitter. But at 25, he's just five months older than heralded prospect Brad Eldred, who's still in Class AA. What's more, he'd look a far sight better at first base for Indianapolis, the Pirates' Class AAA affiliate, than Graham Koonce, who will be 30 next month.

Sanchez, who was reported to throw in the high 90s, was another guy the Pirates inexplicably had no use for. The Los Angeles Dodgers did. He was 3-1 with a 3.38 ERA in 67 games last season. This year, he is 1-1 with a 2.46 ERA and an important member of the bullpen for the team that was the winningest in baseball going into the weekend.

Guerrier, a journeyman at best, was claimed by the Minnesota Twins. He pitched most of last season in the minors. This season he's pitching in relief for the Twins, a team some are picking for the World Series.

All three of these players, two of whom could be in the Pirates' bullpen today and a third who would be one of the best power-hitters in their minor-league system, were given away for nothing.

The Pirates received $50,000 for each of the players lost in the Rule 5 draft. Shelton and Bennett are doing well and look to have major-league careers in front of them. Shelton spent most of last season with the Detroit Tigers where he played sparingly. But in a minor-league rehab stint at Class AAA, he batted .339. After the season, he led the prestigious Arizona Fall League in batting, RBIs, slugging percentage and on-base percentage. He was fifth in home runs. He had more homers than Philadelphia's touted power prospect Ryan Howard.

Bennett played all of last season with Milwaukee and had minimal success. But the Brewers thought enough of him that he's in Class AAA as their designated closer of the future. Thus far with Nashville, he's 0-0 with a 1.23 ERA and three saves.

If the Pirates had protected better prospects than these five, Littlefield's decision might be understandable. But they chose, for reasons that are impossible to fathom, to protect borderline players who had little or no chance at major-league success.

Kept on the 40-man roster in 2004 -- while Young, Sanchez and Guerrier were dropped and Shelton and Bennett were not included -- were the following:

Carlos Rivera: He did not make the Pirates last season out of spring training. He batted .292 with 17 home runs at Nashville. He became a minor-league free agent after the season and signed with the Houston Astros. He is batting .241 with one home run with Round Rock in the Pacific Coast League.

Tony Alvarez: He did not make the Pirates out of spring training. He joined the team briefly and hit .211 in 38 at-bats. He batted .290 with 14 home runs at Nashville. He became a minor-league free agent and signed with the Chicago White Sox. He is batting .211 with no homers for Charlotte in the International League.

Jason Boyd: He was 1-0 with a 5.54 ERA with the Pirates. He was 1-3 with a 3.86 ERA at Nashville. He appears to be out of baseball this year.

Mark Corey: He was 1-2 with a 4.54 ERA with the Pirates and 1-4 with a 4.42 ERA at Nashville. This season he is 0-0 with a 3.18 ERA at Nashville.

None of the four has anything but a slim chance of playing in the majors, let alone excelling. Yet all four were kept ahead of Young, Sanchez, Guerrier, Shelton and Bennett.

The Pirates' evaluation of these players was baffling in 2003. It defies belief today.