"I think it's imperative that we get one at least," Hendry said Monday. "In a perfect world, I could paint a scenario where it would be good to get two, and two from the group we prefer."
That group includes free agent left-hander Ted Lilly, 30, who was 15-13 with a 4.31 ERA in 32 games for Toronto last season. His agent, Larry O'Brien, had not arrived at the Winter Meetings before Hendry's briefing with reporters Monday night. Hendry said rumors that the Cubs had completed a deal earlier in the day were "erroneous."
O'Brien is expected to meet with at least four teams on Tuesday.
The Cubs' rotation now includes Carlos Zambrano, Rich Hill, possibly Sean Marshall and maybe Mark Prior. But the team doesn't want to be caught short-handed, as it was last year, and one possibility, Hendry said, was to move lefty Neal Cotts into the rotation. Cotts, whom the Cubs acquired in a deal with the Chicago White Sox, started four games in 2003 before he was switched to the bullpen.
O'Brien has said he is looking at a deal similar to what Jarrod Washburn signed, which was four years for $37 million. The Cubs spent more than $200 million on six free agents last month, and the payroll is expected to jump to at least $115 million. There is a limit to Hendry's spending spree.
"Sure, there's a ceiling," Hendry said. "You're not players for everybody -- you pick your spots."
Still, the Cubs have money to spend, and Hendry is a popular guy at the Meetings. He talked to a few teams on Monday regarding possible trades, and also talked to some representatives for free agents. He has yet to renew talks with agent Alan Hendricks, whose client, pitcher Jason Schmidt, is a hot topic this week. Hendry and Hendricks talked last month regarding the right-hander.
It's a waiting game now.
"Starting pitching always goes late, because, as history would show, the last three, four years a lot of guys who got a lot of money go late -- it's supply and demand," Hendry said. "A lot of times when you're buying free agent starting pitching, the percentage of success is not great."
If given a choice, Hendry said general managers would prefer to give pitchers shorter contracts, and definitely not a six-year package, rumored to be on free agent Barry Zito's wish list.
"We feel confident we'll come up with some pitching," Hendry said. "You always hope you get this guy or that guy first. If you don't get 'A' or 'B,' then you look at things a little differently."
The rotation isn't Hendry's only project this week. He's also looking at options for the bench, specifically some left-handed bats. Ryan Theriot could be very valuable in that role because of his versatility.
As for the outfield, Hendry said the only thing he guaranteed newly acquired Alfonso Soriano -- besides $136 million over eight years -- is the leadoff spot. He's not sure which outfield position is Soriano's but will make sure that's set, too.
"A lot of things could happen before I say, 'OK, there's your spot,'" Hendry said.
Outfielder Jacque Jones has gotten some interest from teams, who also are inquiring about the Cubs' relievers.
"People look at us as having a deep bullpen, more big-league caliber bullpen guys than we have spots for," Hendry said. "At the same time, we would really like to have a scenario where we gave our young guys more time to develop. The negative of having a year like last year is that you're putting kids up there who are quality prospects who other people value, and if they don't succeed it looks like, 'Oh, the Cubs overrated them.' People from other clubs say these players are valued very highly."
One thing Hendry isn't in the market for is a closer. He expects Ryan Dempster to rebound from a tough season, in which the right-hander went 1-9 with a 4.80 ERA and 24 saves, well off the pace from his 2005 season, in which he was 5-3 with a 3.13 ERA and 33 saves.
"Character," Hendry said when asked why he felt Dempster would be OK. "I saw a guy come back from Tommy John [elbow reconstruction] surgery before most people would have. I saw a guy save 26 games in a row, that nobody had any idea could save games. I know a guy who won't accept failure. I know a guy who, when he hits the first day of Spring Training, will be totally committed to being the guy we saw the year before. I have a lot of faith that Ryan Dempster will be a quality closer."
Back to starting pitching: Can Hendry acquire another arm before leaving the Meetings?
"I hope to have something for you before the week's over," Hendry said. "Some of it is out of my control."
Carrie Muskat is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.