Dempster, 31, went 17-6 with a 2.96 ERA for the Cubs last season after returning to the rotation on a full-time basis for the first time since 2002, and after saving 85 games for the club from 2005-07. He finished in the top seven in the National League in wins, ERA and strikeouts and made the All-Star team for the first time since 2000.
Dempster filed for free agency and spent four days on the market for anybody to pitch offers, but it was always thought that he would likely re-sign with the Cubs. He also received interest from several teams, including the Yankees, Mets, Braves, Dodgers and Blue Jays, but no firm offers.
"I just thought this is where I wanted to be," Dempster said. "Was more money out in the open market? I'm sure there probably was. Who knows, maybe there were five-year [offers potentially], you never know. That's a question that I will never be able to answer. Truthfully, I don't really even care to know. I'm happy with what I have, more money than I can ever dream of getting."
Barring any more moves, the Cubs go into 2009 with the same strong rotation they finished 2008 with: Carlos Zambrano, Dempster, Rich Harden, Ted Lilly and Jason Marquis. The Cubs received a discount to keep that staff intact.
"It was imperative that we kept [Dempster] in house," general manager Jim Hendry said. "He made no secret that he really wanted to be here. There was no doubt in any of our minds that Ryan would have exceeded this deal on the streets three or four weeks from now given the market with starting pitching."
Skeptics can argue that Dempster earned a long-term deal by performing well for just one season as a starter, and a contract year at that. Don't forget, some called for his removal from the closer's role before his successful conversion back to the rotation. Is it worth the gamble?
"He's still got five or six good years in him, no doubt in our mind," Hendry said. "You win a lot of baseball games with this guy on your ballclub. He's had a tremendous influence on a lot of guys in that clubhouse."
The pain of recent playoff losses also played a role in Dempster's decision. Like several of his teammates, he finished the 2008 season with a disappointing performance in the National League Division Series against Los Angeles.
"Maybe we underestimated how prepared you have to be," he said. "In a way we were so good at home, I was so good at home (10-0 to start the year), it almost felt like it was going to be a given that we would win Games 1 and 2."
"Ultimately, it comes down to what our chances are to win a world championship. Getting to the postseason the last two years, I thought this is where I wanted to be."
-- Ryan Dempster
Getting the nod in the opener, Dempster tied a career high by issuing seven walks in 4 2/3 innings. He gave up a crowd-silencing grand slam to James Loney, which propelled the Dodgers to a 7-2 victory, the first step to a series sweep. Despite winning a league-best 97 games, the Cubs went three and out of the playoffs for the second straight year.
"We've got unfinished business," said Dempster, who memorably predicted on the first day of Spring Training that the club would win the World Series for the first time since 1908. "I want to go back out there and have a better year than I had this past season."
Dempster is 76-81 with 87 saves and a 4.55 ERA in parts of 11 Major League seasons. Since joining Chicago prior to the 2004 season, he is 26-26 with 87 saves and a 3.59 ERA. He was an NL All-Star while with the Marlins in 2000.
The Cubs have addressed their two biggest offseason needs -- re-signing Dempster and solidifying the back end of the bullpen by trading for Kevin Gregg. Offensively, the club is still looking for a left-handed bat, perhaps a right fielder.
What does this mean for the interest in Jake Peavy and Randy Johnson? Well, Hendry isn't ruling anything out. He and other Cubs brass will meet Wednesday to map out their interests.
"We're not opposed to continuing to get better," Hendry said. "If it does mean more pitching, then at the right time, if we have a chance to do that, we will."