I would expect the following to happen over the next few weeks:
1. FIRST 15 DAYS AFTER CONCLUSION OF WORLD SERIES: Window during which MLB Article XX free-agents can file for free-agency.
2. 4TH BUSINESS DAY FOLLOWING CONCLUSION OF WORLD SERIES: Deadline for clubs to add their own Rule 55 minor league free-agents (so-called "Six-Year Minor League Free-Agents") to the 40-man roster by selection. (Clubs retain exclusive negotiating rights with their own Rule 55 minor league free-agents through the end of the MLB Free Agency Filing Period).
Probably the only Cubs post-2009 Rule 55 minor league FA who is a candidate for selection to the 40-man roster prior to the deadline 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"). The Cubs claimed Snyder off waivers from Cleveland in September 2008 (he was the Indians #1 draft pick out of Ball State in 2003, and was rated a perennial Cleveland Indians "Top Ten Prospect" by Baseball America 2004-07), and he remained on the Cubs 40-man roster until he was outrighted to AAA Iowa at the end of Spring Training. 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 before 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.
The 27-year old Snyder is presently playing for Mexicali in the Mexican Pacific League (LMP), where he is 11th in the league in SLG and 4th in walks (and tied for 10th in strikeouts). 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 to be a free-agent, I would think he would probably take the opportunity to sign with another organization where he would get a better chance to play in the big leagues next year. My guess is the Cubs let Snyder walk.
3. NOVEMBER 20TH: 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 21-year old RHP Rafael Dolis and/or 25-year old "supersub" 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. (Dolis showed a lot improvement at Instructs, and Camp is presently playing for Mexicali in the LMP where he leads the league in stolen bases, is 6th in the league in hitting, and is tied for 6th in doubles). Adding Dolis and Camp to the MLB Reserve List would bring the Cubs 40-man roster up to 37.
4. DECEMBER 1ST: Deadline for offering salary arbitration to MLB Article XX free-agents.
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 arbitration 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 7TH-10TH: MLB Winter Meetings in Indianapolis.
The Rule 5 Draft will be held Thursday morning 12/10, and is the last order of business at the meetings, While the Cubs have not selected any players in the Major League Phase of the draft for themselves in recent years (the Cubs selected OF Josh Hamilton from Tampa Bay in 2006, but then traded him to Cincinnati for cash), they have had other clubs select players by proxy in each of the last two years, and then acquired the players via trade after selection. In 2007, RHP Tim Lahey was selected by Tampa Bay from Minnesota and then was traded to the Cubs for cash, and last year RHP David Patton was selected by Cincinnati from Colorado, and then was traded to the Cubs for cash. Lahey did not make the Cubs 2008 25-man Opening Day roster and was claimed off waivers by the Phillies (and then was subsequently re-claimed by the Twins later in the season), but Patton remained on the Cubs 25-man roster (or 15-day DL) for the entire 2009 season, and so he is no longer a Rule 5 player, and can be optioned to the minors in 2010 (and he will have three minor league options)
While the Cubs have dabbled in the Major League Phase of the Rule 5 Draft the last couple of years, Cubs minor leaguers have been selected in each of the past seven drafts (ten players total). OF Jason Dubois was selected in 2002 by Toronto, but was re-claimed by the Cubs when Dubois did not make the Jays Opening Day roster in 2003. LHP Andy Sisco was selected by Kansas City and LHP Luke Hagerty was selected by Baltimore and then traded to Florida in December 2003, and while Sisco had an outstanding rookie season working out of the Royals bullpen (he was a contender for A. L. Rookie of the Year) and remained with the Royals for the entire 2004 season, Hagerty (who was still not 100% recovered from 2002 TJS) was re-claimed by the Cubs during Spring Training 2004. RHP Jason Szuminski was selected by Kansas City and then was traded to San Diego in December 2004, and Szuminski did make the Padres 2005 Opening Day 25-man roster, before being re-claimed by the Cubs midway through April when the Padres tried to send him to AAA. RHP Juan Mateo was drafted by St. Louis in 2005, but was re-claimed by the Cubs during Spring Training 2006. In December 2006, INF Jason Smith (who had been signed by the Cubs as a minor league FA just a month prior to the Rule 5 Draft) was selected by Toronto, RHP Lincoln Holdzkom (acquired earlier that year from Florida in the Todd Wellemeyer deal) was selected by Houston, and LHP Edward Campusano was selected by Milwaukee and then traded to Detroit. Holdzkom was re-claimed by the Cubs during Spring Training (but then was released prior to Opening Day 2007), but Smith remained in the big leagues throughout the 2007 season (he was claimed off waivers by Arizona in May, and then was claimed off waivers again by Kansas City in July), and Campusano had a very good Spring Training with Detroit and reportedly had made the Tigers 2007 25-man Opening Day roster, before going down with an elbow injury that required Tommy John Surgery. Campusano spent the entire 2007 season on the Tigers 60-day DL, and then was re-claimed by the Cubs when the Tigers tried to outright him to the minors after the season. RHP Randy Wells was selected by Toronto in December 2007, and he made the Blue Jays 2008 25-man Opening Day roster, before being re-claimed by the Cubs when the Jays tried to outright him to the minors in April. And LHP Donald Veal was drafted by Pittsburgh last year and spent the entire 2009 season on the Pirates 25-man roster (or 15-day DL) and so he is no longer a Rule 5 player. (Veal is presently one of the top 5 starting pitchers in the AFL).
So if history is any predictor of the future, expect one or more Cubs minor leaguers to get selected in the Major League Phase of the 2009 Rule 5 Draft, with about a 70% chance that any Cubs player who is drafted will return to the Cubs. The top ten Cubs minor leaguers most-likely to get selected in the Major League Phase of the Rule 5 Draft this year would probably be (in this order): C Welington Castillo, LHP John Gaub, RHP Blake Parker, RHP Rafael Dolis, IF-OF Matt Camp, C-1B Steve Clevenger, C Chris Robinson, LHP Jeremy Papelbon, OF James Adduci, and RHP Alessandro Maestri, although W. Castillo, Gaub, and Parker are virtual locks to get added to the Cubs 40-man roster by 11/20, while Dolis and Camp are both probably 50/50 at this point (with the final decision on Camp dependent to some extent by how he performs over the next couple of weeks in the Mexican Pacific League)
6. 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 probably 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 contract 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 a roster-slot that could be made available for any FA the Cubs might sign (or re-sign) after 12/12.
It's possible that the Cubs will also non-tender Andres Blanco on 12/12, but only if they know for sure in advance 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 think Neal Cotts will be the only Cubs player eligible for arbitration to get non-tendered, I would not be surprised if Aaron Heilman gets traded before Spring Training (as happened with Michael Wuertz last off-season). Heilman was reportedly claimed by the Giants off Trade Assignment Waivers at the end of August (and then was pulled back by the Cubs), so trading Heilman to San Francisco (possibly as part of a Bradley for Rowand swap?) might be a possibility.
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 (at this point) to have a spot on the Cubs projected 2010 Opening Day 25-man roster. Any American League club looking for a RH platoon DH would be foolish not to have an interest in acquiring Fox.
As for Aaron Miles, because he is guaranteed $2.7M in 2010 and coming off a horrendous 2009 season (185/224/242 in 74 games with the Cubs), he is virtually untradeable, and so I believe he will still be on the Cubs roster come Spring Training. I expect him to be given every opportunity during Spring Training to show he is back to 2008 form (317/368/409 in 134 games with STL), and he will compete with Jeff Baker, Mike Fontenot, and Andres Blanco for a middle-infielder job. But if he continues to suck, Miles will almost certainly get released at the end of Spring Training and the Cubs will just "eat" his contract. So unless the Cubs desperately need his roster slot during the off-season (and that's not very likely), don't expect anything to happen with Aaron Miles until the end of Spring Training.