I would expect the following to happen over the next few weeks:

 

1. NO LATER THAN THE 4TH BUSINESS DAY FOLLOWING CONCLUSION OF WORLD SERIES: Clubs must decide whether to add any of their Rule 55 minor league free-agents to the 40-man roster.

Probably the only Cubs candidate is RF Brad Snyder, who could be another Garrett Jones or Casey McGehee (an apparent "4-A guy" who gets written off but is in reality just a "late bloomer"). Along with Kyler Burke and Nelson Perez, Snyder has one of the top three OF arms in the Cubs organization, has plus-power (he was on a pace to hit 50 HR for Iowa when he broke his wrist in May), runs well for a big guy (he looks like he could play TE in the NFL), and is a decent defender who can play all three OF positions (although RF is best position). His only negative (and it's a big one) is an inability to make consistent contact.

Snyder is presently playing for Mexicali in the Mexican Pacific League (LMP). He is out of minor league options, so adding him to the 40 would mean he would be exposed to waivers again at the end of Spring Training if he doesn't make the Cubs Opening Day 25-man roster. If the Cubs don't add him to the 40, they could try and re-sign him to a minor league contract with an NRI to Spring Training, but if given the chance, he will probably sign with another club where he would get a better chance to play in the big leagues next year. My guess is the Cubs let Snyder walk.

2. FIRST 15 DAYS AFTER CONCLUSION OF WORLD SERIES: Window during which MLB Article XX free-agents can file for free-agency.

Cubs free-agents Chad Fox, John Grabow, Kevin Gregg, Rich Harden, and Reed Johnson will file for free-agency, bringing the Cubs Reserve List (40-man roster) down to 33 players.

3. NO LATER THAN 11/20: Deadline for adding minor league players who are eligible for selection in next month's Rule 5 Draft to the MLB 40-man roster.

I believe the Cubs will add C Welington Castillo, LHP John Gaub, and RHP Blake Parker to the 40-man roster, and they will also outright RHP Marcos Mateo to the minors (presuming he isn't claimed off waivers). This will bring the Cubs 40-man roster up to 35 players.

It's possible that the Cubs will also add RHP Rafael Dolis and/or IF-OF Matt Camp to the 40-man roster on 11/20, too, because if they don't, Dolis and Camp are good candidates to get selected in the Rule 5 Draft. Adding Dolis and Camp to the MLB Reserve List would bring the Cubs roster up to 37.

4. DECEMBER 1ST: Deadline for offering arbitration to MLB Article XX FAs.

I believe the Cubs will offer salary arbitration to Type "A" FA John Grabow, but not to any of the other four. Because Grabow is a Type "A" FA, the Cubs would get a 1st or 2nd round draft pick plus a "sandwich" pick between the 1st and 2nd round if Grabow signs with another club, which would mean most clubs wouldn't be interested in signing him because signing him isn't worth losing a 1st or 2nd round pick. That should drop Grabow's value down and the Cubs should be able to sign him for below market-value. (I say the Cubs should be able to sign him for below market-value, not that they will). But one way or another, I believe Grabow will re-sign with the Cubs. This will bring the Cubs roster up to 38 players.

Reed Johnson might get re-signed eventually, too, but I doubt that he will be offered salary arbitration on 12/1. Before they re-sign Johnson (or offer him arbitration), the Cubs need to know whether they will be exchanging Milton Bradley for a CF or another RF (presuming Bradley even gets traded during the off-season). Because if the Cubs trade Bradley for a CF (like Aaron Rowand, for instance), I doubt that the Cubs would re-sign Reed Johnson to platoon with Kosuke in RF. In fact even if Fukudome plays CF again in 2010, the Cubs might opt to try and make a trade for a cheaper RH hitting OF like Rajai Davis (A's), who is eligible for salary arbitrationn as a "Super Two," but still won't be getting "Reed Johnson money" ($3M per year). I suspect the A's would take Sam Fuld back for Davis.

5. DECEMBER 12TH: Deadline for clubs to tender 2010 Major League contracts to unsigned players on their 40-man roster (auto-renewal guys and arbitration-eligibles).

I believe the Cubs will non-tender only one player, and that is LHP Neal Cotts (who is at Fitch Park rehabbing from July 2009 TJS). They then will try and re-sign him to a 2010 minor league ontract with an MLB split ($150K while he rehabs, then a prorated $900K if and when he is ready to pitch in the big leagues in 2010 and gets added to the 40-man roster). And I believe Cotts would probably take such a deal, too, partly because he isn't likely to get a better offer elsewhere, and partly because I doubt that he would want to uproot his family and change trainers and facilities in the middle of his off-season rehab.

Non-tendering Cotts on 12/12 would bring the 40-man roster down to 37, and would clear another slot to be used for any FA who might get signed (or re-signed, if it's Reed Johnson) after 12/12.

It's also possible that the Cubs will non-tender Andres Blanco on 12/12, but only if they know for sure that they can sign him to a 2010 minor league contract. To do this, the Cubs would probably have to offer Blanco at least $250K plus an NRI to ST. That way, if he makes the Cubs 25-man Opening Day roster, he can be added back to the 40 at the end of Spring Training. And if he doesn't, he can be sent to Iowa (and be available to get called up if needed later in the season) without having to clear waivers at the end of Spring Training (Blanco is out of minor league options).

While I don't think any of the other Cubs arbitration-eligibles will get non-tendered, I would not be surprised if Aaron Heilman gets traded before Spring Training (as happened with Michael Wuertz last off-season).

I also expect Jake Fox to get traded sometime prior to Opening Day, since he is out of minor league options and does not appear to have a spot for 2010.