With 2009 Season Looming, Chicago Cubs Face Questions Crucial to Their Success

With Spring Training just around the corner and the sting of another early exit from the playoffs fresh in the minds of Cubs fans, GM Jim Hendry has been busy, having set out to bolster the team’s roster with more pitchers and what Hendry believes was the cause of the October collapse suffered by the Boys in Blue—the lack of left-handed hitting.

Fans can expect 2009 to taste a bit different than its predecessor did.

Utility player extraordinaire Mark DeRosa, starting pitcher Jason Marquis, and fan-favorite closer Kerry Wood are out, as are a host of reserve players such as Henry Blanco, Ronny Cedeno, and Felix Pie, who just a couple of years back was thought to be the franchise’s top prospect.

In return, the Cubbies have received a slew of minor league prospects and pitchers, including former Marlin Kevin Gregg and Aaron Heilman, previously with the Mets, along with utility man Aaron Miles and outfielder Milton Bradley, both of whom are switch hitters and were brought aboard in an effort to balance the team’s predominately right-handed lineup.

As for Jake Peavy, the Padres pitcher that has been at the center of a firestorm of rumors that he's going to be traded to Chicago, it’s worth noting that while a trade hasn’t been announced, many of the prospects that Hendry has traded for are rumored to have been of interest to Padres GM Kevin Towers when he was shopping Peavy around during Winter Meetings.

Now, with that out of the way, let’s look at the top five questions facing the Cubbies this season.

1) Who is going to fill the fifth spot in the rotation vacated by Jason Marquis?

Marquis was the Cubs’ most inconsistent starter, and picking the right replacement could solidify the rotation as the best in baseball. Aaron Heilman and Sean Marshall are expected to duel for the spot, but a better option would be trading for Peavy, who at 27 has already won a Cy Young and is an outstanding young talent.

With Carlos Zambrano, Rich Harden, Ryan Dempster, Ted Lilly, and Peavy, the rotation would have no equal and would give the Cubbies the edge needed in the playoffs.

2) Can Milton Bradley stay healthy?

When healthy, Bradley is an outstanding player. Last year as a DH with the Rangers he averaged .321 with 22 homers, 77 RBI, and a .436 OBP, and when he’s in the outfield he’s a sound defender. He is also a fiery competitor and should do wonders to help rally the clubhouse when in a slump.

However, he has a history of being injured and the Cubs took a risk by signing him with the expectations that he will be the team’s everyday right fielder. If he stays healthy, though, he’ll be more than worth it.

3) Can the Cubs avoid a letdown in the NL Central?

After going back-to-back as champions of the division, the Cubs have to stay focused and avoid a letdown.

The teams in the Central haven’t improved, and the Brewers, last year’s NL Wild Card, have actually taken a step back, having lost close to a dozen players to free agency, including their two best pitchers, Ben Sheets and CC Sabathia.

As long as they take it one game at a time, the Cubs should three-peat as division champs.

4) Can Carlos Marmol or Kevin Gregg become the shutdown closer the Cubs need to replace Kerry Wood?

It wasn’t the wisest of choices, but Hendry let Wood, who had 34 saves last season, slip into free agency. It’s now up to Marmol, who struck-out 114 with a 2.68 ERA last season, or Gregg, who had 29 saves but blew nine, to step up and take his place.

Gregg has plenty of experience, having been in the league since 2003, but Marmol will provide a stiff challenge and has an excellent chance at winning the job. Regardless of who gets it, they’ve got to be able to win the close games.

5) Will the Cubs overcome the psychological pitfall that has doomed them during the playoffs?

No matter how much the roster changes, it won’t matter who is playing if they hit like a little-leaguer once October rolls around. In the sweeps by both Arizona and Los Angeles, the Cubs hit poorly, pitched poorly, and left runners stranded when they made it on base.

That’s uncharacteristic of such a dominant regular season club, and if the Cubs want to make it the Fall Classic and end their championship drought, they must figure out how to play as well in October as they do from April to September.