Once the postseason rolled around, though, Dempster's spring training prediction that the Cubs would win the World Series fell way short when Chicago was swept in the first round for the second consecutive year.
Dempster had a chance to leave as a free agent, but his desire to get the Cubs to the World Series, help them win it all for the first time since 1908 and play in a city where he and his family are so comfortable were all factors in his decision to return Tuesday.
And a $52 million, four-year contract helped convince him, too.
"I never thought sitting there negotiating over 50-something million dollars would be such a hard thing to do," Dempster said. "Ultimately what it comes to, you have to think: What are our chances to win a world championship? I think given as close as we've gotten the last few, I just thought this is where I want to be."
Dempster struggled in the playoff opener against the Dodgers, throwing 109 pitches in 4 2/3 innings. He gave up four runs and four hits while matching a career high with seven walks. He also allowed a grand slam to James Loney in the Cubs' 7-2 loss.
Now, Dempster will get another chance to help the Cubs end their long drought.
"Maybe we underestimated how prepared you have to be and how ready you have to be, especially in a five-game series. It's like a short heavyweight bout -- ding ding, the bell is ringing and you got to go," Dempster said.
"We were so good at home and I was so good at home, it almost felt like it was just going to be a given that we would win Games 1 and 2 and move on and go from there. You've still got to play the games. ... It felt embarrassing to go out there for a second year in row and to lose three straight games for whatever reason. We have to figure out what it is that is not getting done and have to get better about it," he said.
Dempster said he's not worried that he might have gotten a bigger or better deal elsewhere if he'd spent more time on the market. He said there were no other firm offers immediately, but there were several teams that showed interest, including the Atlanta Braves, New York Mets, New York Yankees, Toronto Blue Jays and Los Angeles Dodgers.
"Was there more money on the open market? I'm sure there probably was. Who knows? Maybe there was five years. You never know," Dempster said.
"That's a question that I'll never be able to answer, but truthfully I don't really even care to know because I'm happy with what I have. It's more money than I could ever dream of getting when I was a kid growing up playing baseball," he said.
Dempster gets a $4 million signing bonus, $8 million next year, $12.5 million in 2010 and $13.5 million in 2011. He has a 2012 option for $14 million.
Dempster can earn an additional $1.85 million a year in award bonuses, a source told ESPN.com's Jayson Stark. His contract also contains escalator clauses worth an additional $9.75 million that would be triggered if he wins one or more Cy Young, MVP, World Series MVP, LCS MVP, Sporting News All Star or Gold Glove awards or places in the top five in Cy Young or MVP voting.
The 31-year-old right-hander was 17-6 with a 2.96 ERA for the Cubs this season.
"It was imperative that we kept him in-house," general manager Jim Hendry said. "No doubt in our minds that Ryan would have exceeded this deal on the streets in three or four weeks from now, the way the market is for starting pitching. Ryan was committed. From day one he told us he wanted to stay. And it was a priority for us to try and get it done before we got too far down the road in the winter."
As the Cubs' closer from 2005-07, Dempster saved 87 games in 102 chances. After earning a spot in the rotation during spring training following rigorous workouts last offseason, he returned to the starter's role he held with the Florida Marlins and Cincinnati Reds from 1998 to 2003.
Dempster went 14-3 at Wrigley Field during the regular season.
"When we were going to give him a chance to make the rotation, there wasn't any doubt in his mind, not only was he going to make it but win at a high level," Hendry said.
"He's still got five or six good years in him," the GM added. "You win a lot of baseball games with this guy on your ballclub."
Hendry said the Cubs couldn't give Wood the long-term deal he deserved because they had more important priorities. And one of those top priorities was re-signing Dempster. Chicago has also explored acquiring San Diego Padres ace Jake Peavy.
"I wouldn't necessarily rule out anything," Hendry said without being specific. He said the Cubs would not hesitate to bring on more pitching if the situation was right, while still hoping to add a left-handed bat.
Hendry, who got a contract extension through 2012 in October, said he expected the team's payroll to increase slightly this season. He said he'd encountered no financial restrictions, even with the team up for sale by Tribune Co.
Information from The Associated Press was used in this report.