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Counting down 2014’s biggest Chicago sports stories: No. 7

The Sun-Times is counting down the 10 biggest Chicago sports stories of the 2014 calendar year one day at a time.

No. 7: Jon Lester signs with Cubs

The eighth item on our list, White Sox phenom Jose Abreu, was a portrait of the future on the South Side.

So it’s only natural that No. 7 offer a glimpse of the future on the North Side.

The Cubs’ signing of Jon Lester – for six years and $155 million — signaled the official transition from a rebuilding process to win-now mode.

“This definitely propels us into Plan A, which is kind of neat. It’s a big day for us moving forward,” Cubs manager Joe Maddon said at the Winter Meetings when the deal was struck. “It’s not often you get to win the lottery. We won the baseball lottery so far this year. It’s up to us now to put it in effect.

“It’s all theory right now. We’ve got to make it real. But you need pieces like this to make it real.”

Lester is a three-time All-Star with two World Series rings. He needs only to win one more to become a Cubs legend.

He went 16-11 with a career-best 2.46 ERA and 220 strikeouts last season with the Red Sox and A’s. Lester is 116-67 with a 3.58 ERA in nine big-league seasons.

Lester, now the second-highest paid pitcher in baseball, was the centerpiece of a busy Cubs offseason that included the additions of Jason Hammel, Miguel Montero and infielder Tommy LaStella. Coupled with the infusion of minor-league talent from the best farm system in baseball, Cubs fans have reason to be excited.

It’s hard not to draw comparisons to the Cubs’ 2006 offseason, which is nothing but a cautionary tale at this point. The Cubs signed Alfonso Soriano to an eight-year, $136 million blockbuster deal that similarly signaled a seismic shift.

The Cubs, as they are now, were coming off a last place finish in the National League Central. In addition to signing Soriano, general manager Jim Hendry re-signed Aramis Ramirez, Kerry Wood, Wade Miller and Henry Blanco. He also added Mark DeRosa and traded for reliever Neal Cotts.

The comparisons end right there, for now.

The Cubs won division titles in 2007 and 2008. Will they do the same in 2015 now that Lester is on board?

Las Vegas seems to think so. The Cubs’ World Series odds have gone from 50-to-1 all the way to 10-to-1 this offseason.

That alone deemed Lester worthy of a spot in our top 10.

The countdown continues with No. 6 on Wednesday. Could the Chicago Bears make their debut in the countdown?

The list so far:

1. Revealed Dec. 31

2. Revealed Dec. 30

3. Revealed Dec. 29

4. Revealed Dec. 26

5. Revealed Dec. 25

6. Revealed Dec. 24

7. Jon Lester signs with Cubs

8. Jose Abreu takes Major League Baseball by storm, wins AL Rookie of the Year

9. Blackhawks’ playoff run reaches Western Conference Finals; Kane, Toews sign 8-year extensions

10. National Labor Relations Board says Northwestern football players are employees, orders union election