MESA, Ariz. -- Jon Lester has been through this before.
He knows all about a desperate fans base going through a difficult drought. He's seen an organization go through a sharp cultural change. He knows what it's like to lose -- a lot.
Lester is also a World Series champion.
OK, so Chicago's North Siders don't know much about the latter, but it's a big reason why the Cubs went out and signed the 31 year-old left-hander to a 6-year, $155-million deal in the offseason.
Not only is he 116-67 with a 3.58 ERA in nine seasons, but Lester brings a know-how and familiarity that falls in line with what the Cubs are trying to accomplish.
"Boston has prepared me for those ups and downs here in Chicago," he said. "I lucked out. I got a lot of things good things going in my direction. I became a free agent at the right time. I'm happy to be here and ready to win."
Lester helped lead the Red Sox to the 2007 World Series title and was in the organization when Boston broke through for its first championship in 2004.
And now he is not tip-toeing around the idea that the Cubs can contend -- and finally put an end to the struggles within the organization.
"It starts with attitude," Lester said after reporting to camp last week." You can work as hard as you want, but if you don't have the right attitude, it's not going to get you anywhere."
"The goals you set have to be high, to the point where you almost can't reach them," he said. "If you set goals that you can consistently reach every year, what's the point of setting goals? You're not making yourself better."?
He picked that credo up as a young starter while working with the Red Sox's Curt Schilling, Tim Wakefield and Josh Beckett during their time during spring training in Fort Myers, Fla., and with the big league club throughout the season.
The hope is he can instill that work ethic in Jake Arrieta, Travis Wood, Felix Doubront, Jason Hammels, Kyle Kendricks, Jacob Turner and others as Chicago looks to make the leap from fifth-place to consistent contenders.
"I put my head down," he said." I do my work. If that makes guys want to follow me then great. If that program doesn't work for them, that's no big deal. It doesn't hurt my feelings."
Cubs President Theo Epstein has already seen evidence of Lester taking a leadership position on the staff.
"He's very serious about connecting with his teammates and the people around him," Epstein said. "He's already leading by example. He's got a smile on his face the rest of the day. He's authentic. He cares about winning, working hard and bonding with his teammates. "He seems even more comfortable than I anticipated he would be."?
Lester, who finished last season with Oakland after a July 31st trade from Boston, is comfortable with his catcher David Ross, who spent some time with Lester in Boston before both signed with the Cubs.
"He has success for a lot of different reasons," Ross said of Lester Monday. "He is definitely deceiving, he throws hard and he as a good angle on his ball. He has good depth to his pitches. He works off his fastball, which he locates well with good movement to both sides of the plate."?
Lester, who is 6-4 with a 2.57 ERA in 14 playoff games, is off to a good start with his first spring training in Arizona: he got his first hole-in-one at Estancia Golf Club in Gilbert soon after arriving in the Valley of the Sun.
"I knew it went in, but I missed it by probably 20 yards and it kicked just dead left and rolled in,"? he said.
Just the kind of help the Cubs hope they get in trying to win their first World Series title since 1908.