Ryan Dempster and Kerry Wood, both key contributors to the team's 97-win season, are free agents, and Cubs general manager Jim Hendry's first priority this offseason is to re-sign the pair.
There is a chance the Cubs will reach an agreement with Dempster before Thursday's deadline. Free agents can only sign with their previous team until then, and other teams cannot talk salary with free agents before that date. After that, it's an open market.
Dempster won a career-high 17 games, posted a 2.96 ERA and threw more than 200 innings in his return to the rotation after 2003 Tommy John surgery and three years as the Cubs' closer. One of the most popular players on the team, there were reports that the Cubs had made a four-year offer to the 31-year-old pitcher.
"Ryan knows we want him to stay here, and he's never expressed a desire that he wants to leave," Hendry said.
There are plenty of pitching-hungry teams that will be interested in Dempster as well as Wood, who converted 34 of 40 save opportunities in his first season as a closer. Wood switched roles in hopes of avoiding any more trouble with his shoulder. His only problem in 2008 was a nagging blister in July that kept him from pitching in the All-Star Game.
Wood's agents also will get phone calls as teams look for help at the back end of the rotation.
"Kerry has done a terrific job in the closing role," Hendry said. "But at the same time, there's a lot of conversations that have to happen with his representatives and him as to what his desires are and what type of contract he's looking for."
If the Cubs don't retain Dempster, they may amp up talks with the Padres regarding right-hander Jake Peavy. The Cubs are one of teams in the hunt for Peavy, who was 19-6 with a 2.54 ERA in 2007 and 10-11 with a 2.85 ERA this past season.
Among the Cubs' other free agents, the team declined to pick up Henry Blanco's option for 2009, but the veteran catcher could still return. Pitcher Bob Howry was not expected to be re-signed, and outfielder Jim Edmonds will not be brought back.
After posting the best record in the National League and winning the Central for the second straight year, both Hendry and Cubs chairman Crane Kenney feel they have a good nucleus heading into 2009. However, there are some issues to be resolved besides pitching. Center field is unsettled, and manager Lou Piniella has talked about moving Kosuke Fukudome there. The Japanese outfielder could share playing time with Reed Johnson and that would create a vacancy in right for another left-handed bat.
In the first year of his four-year, $48 million contract, Fukudome had a Jekyll and Hyde-type season, batting .299 in the first two months of the season and .224 the rest of the year.
"I did tell him we have a lot of faith in him, and we think he's going to be the player not only who we scouted but who we saw in the first half," Hendry said of a chat he had with the outfielder after the playoffs ended. "But we would go about our business, and if the opportunity arises to add another outfielder, we will. He knows he'll have to earn his everyday status."
The Cubs do have first baseman/outfielder Micah Hoffpauir in house. He batted .362 with 25 homers and 100 RBIs at Triple-A Iowa and hit .342 with the big league club. But defensively, he's no Fukudome. Felix Pie is better in the field and has the speed that Piniella covets, but the 23-year-old hasn't been able to make the transition to the big leagues at the plate.
Among the free agent outfield options, players like Manny Ramirez and Bobby Abreu will not fit in the team's 2009 budget. There are other left-handed hitters on the market, including Raul Ibanez and Mark Kotsay.
Kenney has said it's business as usual as the team sorts out its ownership issues, which are not expected to be finalized by the end of the year. That said, the Cubs will not go on a spending spree this winter.
"As far as we're concerned, we're coming off a season when our club won a lot of games, and it's not an old club, which is good," Hendry said. "The general nucleus is solid. We'll shuffle the deck in two or three areas and try to get better before we get to camp, but it's not like we need an overhaul."
Carrie Muskat is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.