The Chicago Cubs have not won a World Series since 1908, a painful 102 years ago.

Their fans have thought “this will be the year” year after year and their front office has been aggressive enough through free agency and trades in recent offseasons to keep expectations high.

But while they have failed to measure up to those expectations, a division that was once between them and the St. Louis Cardinals is now a four-horse race.

Cincinnati emerged this past season as a contender, winning 91 games to take the division over St. Louis by a comfortable spread. They will continue to give opponents fits this upcoming season, as will the Milwaukee Brewers, who made an aggressive trade for ace Zack Greinke, to show how serious they are about 2011.

The Cardinals, with their pitching staff, won’t be chopped liver either and the middle of their lineup is as dangerous as any in baseball.

Where do the Cubs stand? They are coming off a fifth-place finish behind the aforementioned three and the Houston Astros, which have since regressed.

Seventy-five wins were all they mustered. One would think this would propel Hendry to go after the prime free agents, of which there were many.

This was not so, surprisingly enough.

They needed a bat, but they did not target the likes of Adam Dunn, Victor Martinez, Jayson Werth or Adrian Beltre. Instead, they focused on the free-agents a few levels down, ultimately signing slugger Carlos Pena.

Pena, 32, was signed to a one-year deal worth $10.2 million early this offseason. Surely, a solid line at the plate would warrant such an annual salary, right? Hitting .196, no matter that he smacked 24 homers and drove in 84, does not qualify; well below the Mendoza-Line, a putrid average that illustrates his inability to make contact, let alone take advantage of heavy shifts to the right side.

It’s a tremendous amount of money for him, but despite his awful 2010, the signing is a smart one. He walks, strikes out and hits homers—that’s him in a nutshell.

Given this, if he can hit .250, I’m sure the Cubs would be thrilled. First, that average would mean he reaching base at a solid clip, since his walk-rate has been consistently solid; his on-base percentage was .325 last season, which would equate to .414 if he manages the aforementioned batting average.

Second, the increase in average would mean an increase in home runs, of which he hit 116 from 2007-2009.

Hoping he snaps out of his funk and reverses his career trend, Chicago moved onto equally important business. Hendry’s team needed a reliever and they looked no further than Kerry Wood.

As when Ken Griffey Jr. reunited with the Seattle Mariners, Wood’s return to Chicago has a sentimental factor. He was a promising fireballer in the late 1990′s and early 2000′s, and infamously struck out 20 Astros in 1998—a rookie season, during which he whiffed an astonishing 233 batters in only 166 2/3 innings—before suffering a string of elbow injuries that ultimately plagued his career.

Wood, remarkably still only 33, hasn’t made a start since 2006 but has made something of his career nonetheless, saving 62 games since then. Thirty-four of those came in 2008, his final season with Chicago, and knowing his velocity still sits in the mid-90′s, the team intelligently thought a second stint would energize the team.

Matched up with closer Carlos Marmol, the young strike-throwing machine Wood once was, the Cubs have a formidable if not potentially dangerous back end of their bullpen.

But do the Cubs have enough starting pitching to get these two leads to work with? That is up for debate, even with the acquisition of 27-year-old 15-game winner Matt Garza from the Tampa Bay Rays.

Ryan Dempster is steady; Carlos Silva can eat innings if healthy; Randy Wells is fairly durable; but who knows which Carlos Zambrano will show up.

They need the quiet, business-like one who finished last season strong, not the crazy clubhouse cancer who has periodically tried to earn a one-way ticket out of the The North Side. Garza also has let a temper get the best of him, but he they can keep their emotions in check and pitch as they are capable of, Chicago’s pitching staff can match up well against the Reds, Cardinals and Brewers.

They have plenty of competition in their division, let alone the rest of the National League, but with good mixture of youth and veterans in their lineup, a solid bullpen, and a rotation with high upside, Chicago may have reason to dream big yet again.

One of these years has to be their year, right?

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