Hendry, who received a four-year contract extension through the 2012 season on Monday, said he expected to talk with Dempster and his agent in the next few weeks. The Cubs pitcher, who won a career-high 17 games in his first year back in the rotation since 2003, was expected to file for free agency after the World Series ends.
"Ryan knows we want him to stay here, and he's never expressed a desire that he wants to leave," Hendry said Monday. "Certainly, the year he had and type of clubhouse presence he is and total team guy, we certainly have every intention of trying to keep Ryan."
Another free agent to whom Hendry wants to talk is Kerry Wood, who saved 34 games in his first season as the Cubs' closer. A potential hangup could be length of contract.
"We're going to get our plan together, and we'll try to move forward with what we think is best for the organization," Hendry said. "Kerry has done a terrific job in the closing role. 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."
Cubs chairman Crane Kenney did not want to speculate on what the 2009 payroll would be until Hendry and his staff put together a game plan during the organizational meetings, which began Monday in Arizona.
The Cubs did win a National League-best 97 games this year, and Kenney said "the nucleus of the team is pretty [darn] good." He did not anticipate any major offseason moves that would require significant increases in the payroll.
"I'll leave that for Jim and Randy [Bush, assistant general manager] and the guys to work through, and we'll see where we are in a couple weeks," Kenney said.
As for the coaching staff, Hendry said he told them they were welcome back, but had yet to agree to contract terms with any of manager Lou Piniella's staff.
Hendry also met with Kosuke Fukudome before the outfielder left Wrigley Field for Japan.
"Basically, we told him we saw what kind of player he was and could be in the first half of the season, and then we saw the negative part of his game, which was quite poor the last couple months," Hendry said of Fukudome, who batted .279 in the first half and .217 after the All-Star break. "It's hard to put somebody in our memory bank who was a veteran player who had that kind of turnaround in the same season."
Hendry and Bush met with Fukudome and were convinced the outfielder is not lacking bat speed, not out of shape and not too old, but possibly had to go through a learning process in his first season in the U.S. Major Leagues.
"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. "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 want a better balance for their lineup and possibly add some left-handed hitters to the mix.
"It's easy to say that," Hendry said. "Everybody wants more left-handed hitting. Obviously, Fukudome's failures the second half of the year made that situation imperative.
"You don't win 97 games because you're lacking a lot in certain areas. You always want to try to get better, and we will look for extra left-handed-hitting help."
Could Jim Edmonds be considered? Hendry wasn't sure if the veteran outfielder will play in 2009 or retire. One player the Cubs would like to see develop is Felix Pie, who was to play for Licey in the Dominican Republic this offseason. Pie was the Opening Day center fielder, but he spent most of the season at Triple-A Iowa. He batted .241 in 43 games with the Cubs.
"We feel Felix is going to be a good player," Hendry said. "You're talking about a 23-year-old kid. He'll be an out-of-options player. Without any kind of injury or significant change, he'll have a very good chance to make the ballclub out of Spring Training."
Carrie Muskat is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.