How I Would Fix the Chicago Cubs

I challenge anyone on Bleacher Report to find me a general manager in Major League Baseball that has done more wrong in one winter than Hendry did in 2008-09 over the last 20 years.

Gone: Bob Howry, Kerry Wood, Mark DeRosa, Jason Marquis.

In: Aaron Heilman, Kevin Gregg, Aaron Miles, Milton Bradley.

DeRosa is putting up All Star numbers and is now with the Cardinals. Howry's been effective in San Francisco. Marquis was an All Star in Colorado. and Wood has been... well, he's not Kevin Gregg.

Heilman was acquired in a trade for Ronny Cedeno and Garrett Olsen. Olsen, a promising left handed starter acquired for Felix Pie in a deal with Baltimore, could have been a lefty the Cubs used when they had one left hander in the bullpen for a few months.

Pie, by the way, is starting to heat up in Baltimore and is chasing Milton Bradley's miserable offensive totals.

He's tried for almost a decade to find a winning formula, and while you can't blame one man for the Cubs not winning (it's been a century, folks), his efforts last winter to "fix" the best regular season team in the National League were biblically bad.

He needs to go. Step one.

Just because...

Aaron Heilman—gone
Kevin Gregg—gone
Reed Johnson—gone

I would also buy out Aaron Miles' contract ($2.9M) and let a kid like Andres Blanco fill his roster spot. At least Blanco would play defense and hit .220; Miles isn't doing either.

And with Rich Harden.....

There are a few realities that the Cubs need to deal with.

1) Carlos Zambrano is a good pitcher, but crazy.
2) Ted Lilly is good, consistently good*
3) Ryan Dempster is a No. 4 or 5 starter, not a No. 3
4) To expect Randy Wells to do in 2010 what he is in 2009 is naive

The asterisk next to Lilly is because I'll be discussing him more later.

John Lackey is my choice as a free agent starting pitcher for a number of reasons.

First, he's having a down year, which lowers his likely asking price.

Second, he's won big games... specifically World Series games.

Thirdly, he's an ace who would come to Chicago and bump a guy like Dempster down the rotation to where he belongs.

Finally, he's a good pitcher. The Cubs need another good starting pitcher.

I would offer Lackey a similar contract to the one Ryan Dempster got last winter (four years, $52 million).

Let's talk about Ted Lilly for a moment.

First, a quick fun fact: there are six active pitchers in baseball who have won at least 10 games in each of the past seven consecutive seasons. Can you name them?

Here's a cheat: Lilly's one of the six.

If you look at good pitchers being dealt, the cost over the last few years has been enormous.

CC Sabathia robbed Milwaukee of a handful of their best prospects, Cliff Lee took a nice crop of prospects out of Philadelphia, and now Scott Kazmir took a really good looking young lefty out of Anaheim among the three prospects the Rays got this week.

If you look at the group of starting pitchers that figure to be on the trade market this winter, Lilly would jump to near the top of the list if he was part of the mix.

And when you consider the cost of trading for Roy Halladay, a team might be more willing to move three good prospects for a pitcher like Lilly than four or five for Halladay.

Lilly, like Halladay, has just one year left on his contract, so moving him would be something that would certainly have a few suitors.

I would target prospects, specifically I would want at least three good Double-A players, in return. A middle infielder and starting pitching would be my focus.

By moving Lilly for a handful of prospects, you would save $12 million towards the bottom line in 2010 as well.

Answer to the quiz: Lilly, Sabathia, Mark Buehrle, Johan Santana, Javier Vazquez and Derek Lowe.

Earlier this week I proposed a deal of Lee for Texas SS/3B Michael Young. That deal would make sense for both teams. The link is below.

Moving Lee would begin a domino effect on the roster that I will continue to develop in the coming slides.

The key to losing Lee would be to replace him with a sound defensive first baseman, as Lee has made Aramis Ramirez and Ryan Theriot better infielders because of his glove.

In my other piece, I suggest Casey Kotchman be signed as a free agent. I would also, in this scenario, move Ryan Theriot to second base.

Lee, like Lilly, has one year left on his contract. Bringing in Young would cost the Cubs an additional $3 million in 2010, and adding Kotchman would likley add another $5 million (three years, $15 million) to the bottom line.

http://bleacherreport.com/articles/243232-cubs-rangers-lets-make-a-deal

There is one specific name I think the Sox might be enticed by...

Jake Fox.

The White Sox have Matt Thornton to potentially move into the closer role, and they aren't terribly tied to the man who got the final out of the 2005 World Series.

Here's where my Fox—Jenks deal becomes intriguing. Fox's best defensive position is third base, where the Sox currently have super-rookie Gordon Beckham. But Beckham is a natural shortstop.

Currently playing shortstop is Alexei Ramirez, who was all over Web Gems last year while playing second base. Ramirez could either move to center field or back to second base.

If the Sox brought in Fox, who looks every bit of a legit .300-30-90 guy, the Sox could shift their infield over one slot and have a huge upgrade over Chris Getz, who could become trade bait for the Sox during the winter, or Ramirez could play center field between Alex Rios and Carlos Quentin.

This would also free up money for the Sox. Fox is on his rookie contract still, while Jenks is arbitration eligible again this winter and could make as much as $7 million.

Jenks would then become the Cubs closer.

Why not Carlos Marmol? It's very simple in my mind. When you go to your closer, it should be your best guy. The way Marmol has thrown this year, I don't feel comfortable having him be the guy at the end of the bullpen bench; I would want to have someone available to come in and save Marmol's tail if/when he loads the bases.

By replacing Gregg with Jenks, the Cubs would improve the end of the bullpen. The cost of Jenks would likely be similar to Gregg.

Again, lots of this piece is a reality check.

This reality is that the Cubs are stuck with Milton Bradley, at least to begin 2010. He's going to make $9 million next year, and is due another $12 million in 2011.

Nobody wanted him for more than one year last winter, and nobody is going to pay that salary.

But not everything has been bad with Bradley this year. OK, everything that's come out of his mouth has been, but his performance on the diamond has improved.

After the All Star Break, Bradley is batting .310 with a fantastic .429 on-base percentage. That's the Bradley the Cubs paid for in the winter.

What made the change for Bradley after his miserable first half? Quite simply, it's the move of Bradley to second in the batting order. It's where he belongs.

Since moving up to second in the Cubs' lineup, Bradley is batting .352 with a .452 OBP. Those are ideal numbers for a guy hitting in front of the middle of the lineup.

If the Cubs are going to have to play Bradley, put him where he performs best. The numbers indicate that second is where he's best in the lineup, so put him there from the get-go next year.

If Bradley hits to start 2010 like he has in July and August this year, there might be more trade partners willing to take him out of Chicago next year.

* This is ONLY needed if the Cubs move Lilly, as I suggest earlier.

There are a few starters that have good stuff but who, because of various issues, might come cheaper than Lackey, Rich Harden or Lilly's contracts.

Brett Myers, Carl Pavano, and Jarrod Washburn are three pitchers I would be in contact with early in free agency.

As I said earlier, assuming Randy Wells duplicates his success from this year is naive.

Adding a veteran under value like Myers would give the Cubs a pitcher that, when he's right, is good enough to be a first, second, or third starter. And if he's off, it gives the Cubs a chance to pitch Wells or Jeff Samardzija again.

I would offer Brett Myers three years and $18 million with incentives based on performance.

Gone:

Derrek Lee—$13 million
Ted Lilly—$12 million
Rich Harden—$7 million
Kevin Gregg—$4.2 million
Aaron Heilman—$1.7 million
Reed Johnson—$3 million
TOTAL: $40.9 million GONE

In:

Michael Young—$16 million
John Lackey—$13 million
Bobby Jenks—$7 million
Brett Myers—$6 million
Casey Kotchman—$5 million
TOTAL: $47 million IN

What would these changes make the team look like?

Batting order:
1. Kosuke Fukudome, CF
2. Milton Bradley, RF
3. Michael Young, SS
4. Aramis Ramirez, 3B
5. Casey Kotchman, 1B
6. Alfonso Soriano, LF
7. Geovany Soto, C
8. Ryan Theriot, 2B

Bench:
Andres Blanco, Sam Fuld, Koyie Hill, Mike Fontenot, Micah Hoffpauir

Pitching Staff:

Rotation:
Carlos Zambrano
John Lackey
Ryan Dempster
Brett Myers
Tom Gorzelanny/Randy Wells

Bullpen:
Bobby Jenks, Carlos Marmol, Angel Guzman, Sean Marshall, Jeff Samardzija, Jeff Stevens, Wells/Gorzelanny

The bottom line on the team would increase by roughly $6 million under my proposed changes, but would hopefully provide for not only more opportunity for young blood from within the organization to get a chance to play, but would put players into the best position to produce well.

By the end of next season, there could be a move to get Bradley's salary out of town, which would lower the salary number as well.

These are fairly drastic changes, but could turn the roster over enough to get this team back into the playoffs and in position to actually win a series... or two... or three....