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Dave Littlefield had an opportunity to make an immediate impact after being hired as the Pirates’ general manager last June. He
could have traded Jason Kendall and Brian Giles to contending teams for a bushel of top prospects and started a new
era in Pittsburgh baseball.

He didn’t do that, of course, and now the Bucs enter spring training with the same problems they faced a year ago. The major-league
roster lacks talent. The farm system lacks top prospects, thanks largely to the Pirates’ jones for toolsy players and their
inability to teach plate discipline. The team has posted exactly zero winning seasons since Barry Bonds left town nine years
ago. Rebuilding efforts have failed miserably.

For Littlefield to make a positive impact in his first full season as GM, he’ll have to ask himself a question that should guide
most of his decisions. Namely, "where in the success cycle does my team stand?"

The cycle is a baseball continuum on which every team resides. To measure a team’s place in the cycle, assess its talent in the
majors and minors. Can the players in the organization, mixed with a few trade acquisitions and free agents the team could
reasonably sign, yield a competitive team? More precisely, can the team expect to compete while its current core of major-league
players remain productive and under contract?

Apply this test to the Pirates. Can they reasonably expect to build a strong enough supporting cast around Kendall, Giles and
Aramis Ramirez to compete this year? What about in 2003 or 2004? A weak major-league roster, a barren farm system and a pile
of lousy long-term contracts say the odds are against them.

While asking where your team stands may seem like a simple proposition, how many teams truly take stock of their entire organization
on a regular basis? How many devise a coherent plan for success? How many see that plan through by making consistent, intelligent

The Oakland A’s seem to examine their place in the cycle constantly, laying out a logical plan of attack and sticking to it. GM
Billy Beane runs a team that has made the playoffs in consecutive years, one that can compete in the future thanks to its nucleus of
young players, many of whom are under contract for the next three seasons.

To gain cost certainty, Beane avoided arbitration and signed core players like Mark Mulder and Miguel Tejada to
long-term deals. When he’s seen a need, he’s addressed it the best way he could given his limited budget. The A’s have mixed a
string of productive low-risk free agents like Olmedo Saenz with strategic trades for bigger names like Randy Velarde,
Johnny Damon, and Jermaine Dye. The A’s are at the competing point in the cycle, and Beane’s actions reflect

New Toronto GM J.P. Ricciardi took stock of the Jays’ future almost immediately after taking the helm in November. He cleared out
non-essential players signed to pricey contracts–Alex Gonzalez and Paul Quantrill among them–to free budget space
and clear a path for talented prospects. He filled holes by trading replaceable players for young talent like Luke Prokopec
and Eric Hinske. He held on to the Jays’ nucleus, including Carlos Delgado and Shannon Stewart.

Having a core with which you can win, but arranging the talent around that core, puts the Jays at the building portion of the
cycle. If all goes well, they’ll be competing very soon, maybe by next year.

The A’s and Jays share several common traits. Through years of working side-by-side in Oakland, Beane and Ricciardi both learned to
emphasize in-house player development, to identify inexpensive talent, and to replace non-essential players when needed. Every
decision’s importance is magnified, as both teams lack the larger budgets that their higher-revenue competition possess.

Recognizing a team’s place in the cycle is perhaps the key element in any team’s game plan, because it drives decision-making. If a
GM misreads his team’s place in the cycle, he may get overaggressive and commit too much cash in an effort to win before a core is
in place, and quickly fall back to the rebuilding stage. On the other hand, being too passive with a team ready to win can
cost the franchise a shot at a pennant.

Judging from his actions, you wonder how often Littlefield’s predecessor Cam Bonifay considered his team’s big picture. At the start
of the 1997 season, the Pirates stood at the same point in the cycle where they sit now, with an unproductive farm system and no
recent history of big-league success.

In an effort to upgrade the organization and build a contending major-league team, Bonifay kicked off what he called his five-year
plan. He tied his plan to the opening of PNC Park in 2001.

Bonifay’s plan had precedent on its side. Former Cleveland GM John Hart took control of a flailing Indians’ franchise following a
string of awful years in the late 1980s. Lacking talent at all levels, with fan interest in a rut and little help in sight, Hart
devised a plan to build through the farm system, keep his best players out of arbitration by signing them to long-term contracts.
When the new park opened, he had a winning team on the field and he could funnel a lucrative revenue stream from the new stadium
into filling holes on the Indians’ roster.

Since Jacobs Field opened in 1994, the Indians have posted eight winning seasons in a row, including six division titles and two
American League pennants.

Bonifay’s plan started to take hold in 1998. The Pirates finished 69-93, but Kendall emerged as an elite young player and Ramirez
saw his first major-league action as a 20-year-old. Prospects like Jose Guillen and Lou Collier began seeing regular
playing time. Others like Chad Hermansen started making noise in the minors. The Bucs were clearly moving forward in the
success cycle.

Trying to help his team take the next step, owner Kevin McClatchy green-lighted a huge payroll hike following that season.

We may never know exactly what Bonifay was thinking in the months and years that followed. Maybe he saw the Pirates, a team still in
the building phase, as a veteran or two away from a string of division titles like the one Barry Bonds, Bobby Bonilla
and company had racked up in the early ’90s. Maybe he lost sight of his plan. Whatever the reason, Bonifay went on a binge, signing
replaceable players such as Pat Meares, Mike Benjamin, and Pete Schourek to multi-year contracts. When those
moves failed, he chased them with more bad signings: Derek Bell,and Terry Mulholland. He overpaid Kevin Young.
He traded Jon Lieber for Brant Brown.

Beyond those mistakes, Bonifay oversaw a string of spotty drafts. Emphasizing tools over performance, he watched prospect after
prospect flame out in the minors. Most of the few that made the majors, including Guillen and Collier, eventually flopped. When
Bonifay got his walking papers last June, the team stood at the same point in the cycle where it had been four years earlier.

So how is Bonifay’s successor doing? Has he made moves that would suggest he understands the success cycle and his team’s place in
it? Thus far, Littlefield looks like he’s built a plan and started to carry it out. He traded a raft of players who were nearing
free agency and a huge pay raise or who wouldn’t offer much to the next winning Pirates team.

He flipped Terry Mulholland to L.A. for pitching prospect Adrian Burnside. He nabbed Ryan Vogelsong and Armando
from San Francisco for Jason Schmidt and John Vander Wal. Spotting the difference between a shrewd low-cost
pickup and a rotation anchor, he shipped Todd Ritchie to the White Sox for Kip Wells, Josh Fogg, and Sean
. He grabbed Tony McKnight from Houston for a two-month rental on Mike Williams, then got Williams back cheap
in the off-season.

You could even make a case for the signing of OBP-sieve Pokey Reese, given the Pirates’ organizational lack of middle-infield
depth and Reese’s relatively low price. As a shortstop, and as a #8 hitter, Reese can contribute to a winning team. It remains to be
seen whether he’ll play either of those roles.

Littlefield is acting as the caretaker of a team in the rebuilding part of the success cycle. So far, he has mostly proved that he
can reach low-hanging fruit. Sure, the Pirates did better getting promising prospects for players like Schmidt, Williams, and
Mulholland than letting them go for, at most, draft-pick compensation. But those moves don’t fully tell us if Littlefield holds a
firm grip on his team’s future.

Brian Giles relayed some candid words to Pittsburgh Post-Gazette writer Robert Dvorchak:

"There’s no more excuses for this organization. We had a five-year plan. We’ve been in the new ballpark for a year. If we don’t
win, this whole thing is kind of a failure."

The problem for Giles and the Pirates is that The old plan has already failed. The influx of new talent last year can’t mask the
team’s holes at first base, second base, shortstop, center field, and right field, its patchwork pitching staff or its lack of
promising talent on the farm.

The Pirates locked Giles up through 2005 and Kendall through 2006, but seem unlikely to contend in the small window before those two
exit their prime. Keeping Pittsburgh’s two popular stars around to appease the fans, then watching the team go nowhere for four or
five more years, won’t help. A team rebuilding has to go all the way with the process; failing to commit is a recipe for disaster.

While Billy Beane has built his reputation on identifying talent, one of Oakland’s keys to success has been knowing when to let
players go. In the midst of a playoff run in 1999, he traded de facto ace Kenny Rogers and closer Billy Taylor to the
Mets, then had Tim Hudson and Jason Isringhausen fill those roles. After the 2000 season he dealt Ben Grieve
and filled his spot with Johnny Damon. This offseason he let Damon go and traded for David Justice.

Beane’s biggest test of all was Jason Giambi. After his 2000 MVP season, Giambi told A’s management he’d likely play out the
2001 season, then test the free-agent market. Beane had to decide where his team stood in the cycle. With three young aces in
Hudson, Mark Mulder, and Barry Zito, and a strong offensive core in Miguel Tejada and Eric Chavez, Beane
saw a chance to win the World Series and kept Giambi in Oakland for the season, rather than trade him for future value.

The team started terribly, falling out of the AL West race by June. Though they still had a shot at the wild card, Beane knew he
could land a king’s ransom in prospects for Giambi. He also knew his young core would remain the key to the team’s long-term
success, and that the chances of signing his superstar were slim.

He rolled the dice anyway. The A’s kept Giambi, and traded second-base prospect Jose Ortiz for Jermaine Dye. Fueled by a huge
second half, they rolled into the playoffs. The A’s lost to the Yankees, but Beane felt secure, knowing he’d taken his shot and
still had a strong team behind him. Beane’s recognition that the A’s had passed from building to contending was a key factor in
every move he made.

Giles and Kendall are Littlefield’s Giambi. The Pirates need a talented young core to rival Oakland’s if they hope to compete on a
regular basis. With most of his other chits gone and little minor-league help on the way, trading his stars is Littlefield’s best

It’s easy to want to sign all your stars to long-term deals. Knowing when to let go is much tougher. The sooner Littlefield lets go,
the sooner the Pirates can start their long climb back.

Jonah Keri has covered sports business for Street & Smith’s Sports Business Journal and other publications. You can contact
him at

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