A Big Week Ahead for the Cubs?

Will the Cubs land Jake Peavy? Will they resign Ryan Dempster before he hits the open market? What about Kerry Wood? Will Jim Hendry dive right into the free agent pool on Friday and make any additions to his roster? Those are just a few of the questions that could be answered in the coming week.

Jim Hendry has until midnight on Thursday to resign both Ryan Dempster and Kerry Wood…before he loses exclusive negotiating rights with two of his All Stars. At 12:01am (Eastern) on Friday, players are free to negotiate and sign deals with teams other than their previous organization. In between, talking with the agents for Wood and Dempster, the long distance charges on Hendry’s cell phone figure to increase this week as well…..with the ongoing discussions with Kevin Towers over Jake Peavy.

Some reports suggest a deal could be done for Jake Peavy in the coming week, with the Cubs and Braves considered the leaders in the proverbial clubhouse to land the 2007 NL Cy Young Award recipient….other reports have Peavy traded sometime before Thanksgiving. Will Trader Jim be able to land his man?

The first of the BBWAA awards will be announced this week as well. The National League and American League Rookies of the Year announcement will be made on Monday with Geovany Soto the favorite to land the award in the Senior Circuit. The NL Cy Young (Tuesday), the NL and AL Manager of the Year (Wednesday) and the AL Cy Young (Thursday) will also be announced over the next week.

Here is a prediction on landing spots for a couple of the big name free agents and an updated off-season calendar….


John Perrotto made a few predictions Sunday on Baseball Prospectus on where the top 25 free agents will possibly sign this off-season. A majority of the article is by subscription only, but here is a quick look at where he thinks a few of the Cubs’ free agents will land and the one free agent he thinks Jim Hendry will sign.

  • CC Sabathia – The Cubs “will make a play” but in the end, Sabathia will sign with the Yankees.
  • Raul Ibanez – The Cubs “are after him” but Ibanez will sign with the Mets according to Perrotto.
  • Ryan Dempster – Dempster is receiving interest from the Mets and Braves, but according to Perrotto, Dempster will resign with the Cubs for the rumored 4-year, $50 million dollar deal.
  • Milton Bradley – Bradley is North of the Border bound according to Perrotto.
  • Adam Dunn – Despite the fact Dunn is better suited to be a designated hitter in the AL, Perrotto thinks he will sign with the Cubs. Perrotto labeled his prediction as “being out on a limb” and added “playing right field in Wrigley will prove to be quite an adventure.
  • Bobby Abreu – Not on the North Side but back to the Bronx according to Perrotto.
  • Kerry Wood – The last Cub to win the NL Rookie of the Year Award will be back in Lou Piniella’s pen next season….and beyond according to Perrotto.

2008 – 2009 Off-Season Calendar


  • 10 – End of Waiver period
  • 11 – Beginning of New Waiver period
  • 13 – Last Day of Exclusive Negotiating Rights for Potential Free Agents
  • 14 – First Day Major League Free Agents may negotiate and sign with a team other than their former club
  • 20 – Day to file reserve lists for all Major and Minor League levels

BBWAA Awards

  • 10 – NL and AL Rookie of the Year
  • 11 – NL Cy Young Award
  • 12 – NL and AL Manager of the Year
  • 13 – AL Cy Young Award
  • 17 – NL Most Valuable Player
  • 18 – AL Most Valuable Player


  • 1 – Last date for former club to offer salary arbitration to ranked XX(B) free agents in order to be eligible for compensation. Deadline is midnight eastern
  • 1 – 2009 Hall of Fame Ballot Released
  • 4 – Last day to request outright waivers to assign player prior to the Rule 5 Draft
  • 7 – Last date for player who declared free agency under Art. XX (B) to accept arbitration offer from former club. Deadline is midnight eastern.
  • 8 – 5:00pm EST last time to outright a player prior to the Rule 5 Draft
  • 8 – Hall of Fame Veterans Committee Results Announced
  • 8 – 11 – Baseball Winter Meetings in Las Vegas, Nevada
  • 9 – Ford Frick Award Winner Announced
  • 10 – Spink Award Winner Announced
  • 11 – Rule 5 Draft
  • 12 – Last day to tender contracts. Deadline is midnight eastern



  • 1 – Launch of MLB Network
  • 5 – 15 – Salary arbitration filing period
  • 12 – 2009 Hall of Fame results announced
  • 16 – 18 – 24th Annual Cubs Convention
  • 19 – Exchange of salary arbitration figures


  • 1 – 21 – Salary arbitration hearings
  • 14 – First date pitchers and catchers may report to Spring Training
  • 15 – End of Waiver Period
  • 16 – Beginning of New Waiver Period
  • 17 – First date all players may report to Spring Training
  • 22 – Mandatory Spring Training reporting date
  • 25 – Cactus League Season Begins
  • 26 – Cubs versus Brewers at HoHoKam Park in Mesa


  • 5 – Opening of 2009 World Baseball Classic
  • 5 – 23 – 2009 World Baseball Classic


  • 5 – MLB Opening Night
  • 6 – Opening Day for Chicago Cubs in Houston
  • 13 – Cubs Home Opener against the Colorado Rockies

Well, that’s the latest….and I’m sticking to it!

Quote of the Day

"Don’t ever permit the pressure to exceed the pleasure." - Joe Maddon