Those were high times for the franchise. Holding firm to the belief that Major League Baseball wouldn't move the Montreal Expos just down the road to Washington, the Orioles made a big push on the free-agent market.
They landed Tejada, even drawing mild criticism within the industry for overpaying. And they had the richest offer on the table for Guerrero when he signed for less with the Anaheim Angels.
Still, the Orioles came away with one of their biggest offseason hauls in franchise history, spending $121.5 million to net Tejada, Javy Lopez, Rafael Palmeiro and Sidney Ponson.
Only one year later, the story has changed. With little more than a month until spring training, the Orioles have yet to make their first significant addition of the offseason. A perception has built that Flanagan and fellow Orioles vice president Jim Beattie are moving too slowly.
They fell short in their efforts to sign free agents Carl Pavano and Richie Sexson. And even with Carlos Delgado sitting in the market, practically begging them to make a push, they haven't moved on an offer they made in mid-December.
So how has it come to this? Is the new team in Washington making life that difficult? Or have Beattie and Flanagan suddenly forgotten how to do their jobs? When pressed last week, Flanagan acknowledged that the Orioles haven't been as aggressive with free agents as they were last year. But they have their reasons.
"It's a combination of a high market [for players' salaries], and not having an idea what our future looks like," he said.
Until last Sunday, the Orioles were careful not to speak about the difficulties they've been facing as owner Peter Angelos negotiates a settlement with Major League Baseball over the Expos' move to Washington.
But last week, Flanagan didn't hold back.
"I think it's had a considerable effect this offseason," he said. "If you owned a McDonald's franchise, no one else could put a McDonald's within a certain radius, two or three miles. You could put a Burger King right next door, but not a McDonald's."
The negotiations have been a roller-coaster ride. At one point, it seemed MLB was ready to hand them a generous commitment. Then, there was the long stretch when it looked as though the D.C. council had ended the Expos' move altogether. And now there's a very real sense the Orioles might have to sue MLB to protect their long-range investment.
"It seems," Flanagan said, "like we're always hanging on our next meeting [with MLB]."
A year ago, the Washington scenario loomed, but based on his conversations with commissioner Bud Selig, Angelos was confident baseball wasn't coming to the nation's capital.
The future seemed bright. The Orioles had plans to start their own regional cable network to help them keep up with the New York Yankees and Boston Red Sox. Stretching from Lancaster, Pa., to North Carolina, the Orioles could envision a bigger cable network than the New England Sports Network is for the Red Sox. It would be second only to the Yankees' YES network.
That was then
With a slew of bad contracts coming off their books, the Orioles took advantage of their financial position in a buyers' market. Making Tejada their primary target, they pushed the envelope and eventually out-muscled the Seattle Mariners and Detroit Tigers with a six-year, $72 million offer.
The Orioles swung and missed for Guerrero, even with a $78 million bid, as the Angels landed him with a contract that guaranteed him $70 million. But there's no doubt the Orioles tried.
Now, with the Washington Nationals set to open business this year, their financial picture looks ominous. Last week, Orioles president Joe Foss cited estimates from the accounting firm of Deloitte Touche that say the club will lose between $20 million and $30 million annually.
Beattie and Flanagan have targeted a few free agents they like, but this time they've proceeded with caution.
"What frustrates a lot of agents is they're the nicest people in baseball, but they're slow to react to the market," one agent said last week. "If you're prepared as a front office, you should know when an agent is misrepresenting the market or not.
"I'm not saying they're not knowledgeable, but there seems to be an inability to gauge the marketplace. Jim and Mike have been making offers to players that are significantly lower than other teams, and by the time they respond, it's too late."
This is how it's done
Flanagan said any initial offer the Orioles make is meant to be a starting point for negotiations. Often, he said, the agents counter with a number that looks equally off to them.
This appears to be the case with Delgado.
In mid-December, the Orioles started him with an offer for three years and about $30 million. This month, Delgado countered with a request for four or five years at about $60 million to $75 million.
Those negotiations have gone nowhere, and the Orioles haven't blinked, even with Delgado meeting with New York Mets and Florida Marlins officials in recent days. While the rest of baseball waited for them to move, Beattie and Flanagan refused to push Delgado's market forward.
Trying not to put all their eggs into one basket, the Orioles also continue to monitor the trade front. Industry sources say they have talked to the Tampa Bay Devil Rays about Aubrey Huff and to the New York Mets about Mike Cameron, though neither deal appears imminent.
Ultimately, there's only so much the Orioles can do. When the Yankees signed Pavano, and the Mariners signed Sexson, Flanagan called it a "geographic bias." Pavano wanted to pitch closer to his parents' Connecticut home, and Sexson makes his offseason home in Vancouver, Wash.
A pitch for the future
In December, the Orioles gave Pavano a grand tour of Camden Yards - complete with a video tribute on the scoreboard - and then made him a three-year, $25 million offer with escalator clauses that could have brought the value to $30 million.
Shortly before Pavano made his decision, his agent, Scott Shapiro, called Angelos and nudged him forward, telling him most of the offers were in the four-year, $40 million range. That night, the Orioles came through with that exact offer, but Pavano wound up signing with the Yankees for slightly less guaranteed money.
"At the end of the day, it was an emotional decision for Carl, and there wasn't anything else the Orioles could have done," Shapiro said last week. "[The Orioles] were right there with us. It was not the actions of the Orioles' front office. That had nothing to do with Carl's decision."
NOTE: Delgado met with the Marlins yesterday, and the team made a favorable impression in its bid to sign the first baseman.
Florida earlier offered him a three-year, $35 million deal. His agent, David Sloane, and Marlins general manager Larry Beinfest agreed that the meeting went well.
"The meeting we had was a very good one," said Sloane, who told The New York Times that he made a contract proposal to the Marlins during the 5 1/2 -hour session.
"If someone had told me a month ago we would be involved in discussions with the Florida Marlins, I would have thought that's a long shot. After the meeting we had today, I consider them significantly less of a long shot."
Delgado met Thursday with Mets executives in his native Puerto Rico. He's also being wooed by the Texas Rangers and Red Sox, in addition to the Orioles.
The Associated Press contributed to this article.