Now the veteran right-hander -- probably the most coveted starting pitcher remaining on the free-agent market -- is facing an uncertain picture as agent Scott Boras attempts to navigate his remaining options.
The Phillies and Yankees had been reported to be Lowe's most interested pursuers during the Winter Meetings, but both clubs have moved to thicken their respective rotations without approaching the four-year deal worth between $60 million and $64 million that Lowe is seeking.
Philadelphia on Monday signed 46-year-old Jamie Moyer to a two-year guaranteed contract and Chan Ho Park to a one-year, $2.5 million deal, contingent upon a physical.
Though Park is viewed as organizational depth by general manager Ruben Amaro Jr., the defending World Series champions will begin the 2009 season with Moyer, Cole Hamels, Brett Myers and Joe Blanton in their rotation, reducing their need for further help.
In Philadelphia circles, Lowe was largely viewed as a fallback option if they were unable to retain Moyer, who went 16-7 with a 3.71 ERA in 33 starts last year.
This follows a week in which New York acted swiftly to spend a combined $243.5 million on CC Sabathia and A.J. Burnett, signing both in blockbuster free-agent moves. That leaves the Yankees with just one more slot to fill in their rotation behind Chien-Ming Wang and Joba Chamberlain.
The organization would like that spot to go to Andy Pettitte, who is mulling a one-year, $10 million offer. Pettitte wants to pitch for the Yankees, but he does not want to accept a pay cut from the $16 million he earned in 2007 and 2008.
If the two sides are able to agree on an acceptable number, that will all but remove all chance of Lowe pitching for the Yankees in 2009.
With a resume of postseason success and a durable reputation, Lowe is one of the better options available this winter. But he also comes armed with the forces of the Boras agency, which ensures two things -- the process will take some time, and Lowe's bank account will be quite healthy by the end of it.
That has left the remaining suitors with some concern. One baseball source said that teams were wary because Lowe was thought to be looking for "Barry Zito money," a reference to the left-hander's deal with the Giants that pays him $18.5 million in each of the next three seasons before increasing additionally for the remaining two years.
Lowe is not looking for a seven-year commitment like Zito's, but the high price tag has left clubs considering other routes. Sources close to Lowe have mentioned that the idea of rejoining the Red Sox appeals to him, though Boston's interest has been muted while general manager Theo Epstein focuses on Mark Teixeira.
The Red Sox may take a closer look, however, if the price tag comes down to the arena of four years and $52 million. Those figures may also interest the Mets, with their bullpen much improved and the starting rotation needing a replacement for the innings that both Oliver Perez and Pedro Martinez provided.
One place Lowe will not wind up is Atlanta, even though the Braves struck out on wooing Burnett. Braves GM Frank Wren has made it known that he will not pursue Lowe.
Last week, Lowe spoke about the opportunity to add to his list of postseason experiences as a major factor in deciding on a destination.
"With me, it's all about winning," Lowe said. "The team with the best chance of winning, year in and year out, is where I want to go. Scott understands that. I've already had clubs contact us that are interested, but they're not ready to win.
"Scott knows that's my No. 1 priority, and he's looking out for my best interest. He's done exactly what I've been talking about."
Also appearing certain is that Lowe will not be back in Los Angeles come April. Dodgers GM Ned Colletti said that he is prepared to move on without Lowe in the fold, saying, "I don't believe Derek Lowe will pitch for the Dodgers next year."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.