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The impossible has happened.  The Cubs won the World Series.  Millions of Cubs fans are now contemplating something their parents and grandparents never could: a potential dynasty.  While Theo Epstein, Jed Hoyer, and the rest of the Cubs’ front office have a free pass for life in Chicago, they’re already plotting an encore.  What’s next for the Cubs?

Guaranteed Contracts

• Jon Lester, SP: $90MM through 2020.  Includes $25MM mutual option for 2021 with a $10MM buyout.  2021 option becomes guaranteed with 200 innings in 2020 or 400 innings in 2019-20.
• Jason Heyward, RF: $149MM through 2023.  Heyward can opt out of contract after 2018 season or after 2019 season with 550 plate appearances in 2019.
• John Lackey, SP: $12.5MM through 2017.
• Miguel Montero, C: $14MM through 2017.
• Ben Zobrist, OF/2B: $44MM through 2019.
• Anthony Rizzo, 1B: $27MM through 2019.  Includes $14.5MM club option with a $2MM buyout for 2020 and an identical club option for 2021.  2019 salaries can increase based on MVP finishes.  Rizzo can void 2021 option with top two finish in 2017-19 MVP voting and subsequent trade.
• Jorge Soler, OF: $15MM through 2020.  Can opt into arbitration after 2017 season.

Contract Options

• Jason Hammel, SP: Cubs chose $2MM buyout over $12MM club option.
• Dexter Fowler, CF: Fowler declined his part of $9MM mutual option, triggering $5MM buyout.

Arbitration Eligible Players (service time in parentheses; link to MLBTR projections)

• Pedro Strop (5.156) – $5.5MM
• Jake Arrieta (5.145) – $16.8MM
• Hector Rondon (4.000) – $5.7MM
• Justin Grimm (3.170) – $1.8MM
• Munenori Kawasaki (3.002) – $800K
• Non-tender candidate: Kawasaki

Free Agents

• Jason Hammel, Dexter Fowler, David Ross, Chris Coghlan, Trevor Cahill, Travis Wood, Aroldis Chapman, Joe Smith

The 2016 Cubs had the best starting rotation in baseball by a long shot, and they had the rare ability to bring back the exact same group for 2017: Jon Lester, Jake Arrieta, Kyle Hendricks, John Lackey, and Jason Hammel.  Instead, Epstein kicked off the offseason with a surprising move that won’t go unnoticed by future free agents.  The Cubs declined their option on Hammel, who posted a 3.79 ERA over two seasons for the club.  The 34-year-old might have profiled as the best fifth starter in baseball.  The Cubs feel they can do better, and didn’t feel the need to exercise the option and trade Hammel, which could have brought a low-level prospect in return.  Epstein said in a statement, “Our hope is that by giving a starting opportunity to some younger pitchers under multiple years of club control, we can unearth a starter who will help us not only in 2017 but also in 2018 and beyond.”

One internal possibility is Mike Montgomery, the 27-year-old lefty the Cubs acquired from the Mariners in a July trade.  Montgomery pitched well in his five starts for the Cubs, though his control remains an issue.  Montgomery also made the short list of Joe Maddon’s trusted relievers as the team continued through the playoffs.  Moving him to the rotation is a viable option, though it would open up a hole in the bullpen.  Southpaw Rob Zastryzny, the Cubs’ second round draft pick in 2013, is another rotation option.  However, with a 4.31 ERA across 23 starts at Double and Triple-A this year, Zastryzny would seem a clear downgrade from Hammel.

The free agent market for starting pitching is historically weak.  The only pitcher clearly better than Hammel is former Cub Rich Hill, a brittle lefty who turns 37 in March and would hardly fit Epstein’s search for a younger starter.  That brings us to the trade market.  Possible candidates include Chris Archer, Jake Odorizzi, Drew Smyly, Chris Sale, Jose Quintana, Sonny Gray, and Shelby Miller, all of whom are controllable for multiple years.  The potential prizes of the market are Sale and Quintana, but the White Sox could be reluctant to send one of their aces across town. The Cubs have plenty of position players they might consider trading, including Jorge Soler on the Major League side and prospects such as Ian Happ, Eloy Jimenez, Jeimer Candelario, and Mark Zagunis.  The Cubs already spent a few pieces from their stash this summer, trading Gleyber Torres to get Aroldis Chapman and Dan Vogelbach to get Montgomery.

The Chicago bullpen will require serious work this winter.  Though Hector Rondon and Pedro Strop handled the late innings ably for much of the season for the Cubs, Joe Maddon seemed to lose faith in them as the playoffs wore on.  With combined arbitration salaries over $11MM, I can see the Cubs trading one of them.  Justin Grimm is more affordable, and despite some issues with free passes, he’s worth keeping around.  Carl Edwards Jr. is locked in as one of the Cubs’ more trusted relievers.  Montgomery will certainly have a spot if he doesn’t land in the rotation.  Travis Wood may leave for greener pastures (and a rotation job) as a free agent, while Trevor Cahill and Joe Smith did not make the playoff roster and will likely be allowed to sign elsewhere.

It is difficult to picture a team as stacked with talent and flush with money as the Cubs, coming off a World Championship, not striving for a relief ace.  The free agent market happens to offer two of them, Aroldis Chapman and Kenley Jansen.  However, as Ken Rosenthal of FOX Sports pointed out recently, signing Chapman or Jansen to a five-year deal in the $80-90MM range doesn’t fit with Epstein’s history.  And Cubs GM Jed Hoyer recently expounded on “trying to be creative in finding bullpen pieces,” perhaps discovering the next Andrew Miller or Wade Davis.  Andrew Cashner, anyone?

While the Cubs could turn to the trade market for a dominant reliever, options are limited.  The Orioles’ Zach Britton or the Royals’ Kelvin Herrera would be excellent two-year additions, but they are not known to be available.  Davis, a potential one-year pickup from Kansas City, battled a flexor strain in his elbow this summer.  Barring availability of the Indians’ Andrew Miller, I don’t see any other established top relievers the Cubs could pursue.  Rather than bring in a lesser closer, they could just try to get Rondon back on track, as he had an excellent season before an August triceps injury.  We also must consider Epstein’s ability to think outside the box, as he did in trading for Montgomery.  If the Cubs’ front office is big on a Tyler Thornburg, Nate Jones, or Alex Colome, they could use their position player depth to pry one of them loose.   Regardless of the closer situation, the Cubs may do well to add another lefty reliever to the mix, with free agent options such as Brett Cecil, Boone Logan, Jerry Blevins, and Mike Dunn.

On the position player side, the Cubs have an embarrassment of riches.  Behind the plate, 24-year-old Willson Contreras will be the starter after a strong rookie debut.  Given his salary, the Cubs will likely go with Miguel Montero as the backup catcher replacement for the retiring David Ross.  However, Maddon and Montero will have to clear the air after the catcher expressed discontent with the manager’s communication about his usage in the playoffs.  It’s also not clear whether Montero can fill Ross’ role, particularly in regard to countering the large leadoffs baserunners are able to take on Jon Lester due to the lefty’s inability to make pickoff throws.  Since Contreras is only 24, it may be possible for the Cubs to lean on him for 130-140 games while reducing the role of the backup and ending the idea of Lester having a personal catcher.

The infield corners are locked down with one of the best duos in baseball, Anthony Rizzo and Kris Bryant.  Bryant, a third baseman by trade, also logged innings at the outfield corners and first base this year.  If the playoffs are any indication, Javier Baez has taken over the Cubs’ regular second base job from Ben Zobrist.  Addison Russell is locked in at shortstop.

The Cubs’ outfield machinations will be interesting to watch.  Fowler did an excellent job as the Cubs’ center fielder and sparkplug leadoff man over the last two seasons, and the team could easily afford to sign him long-term.  But doing so would only exacerbate the outfield logjam, so they may have to let him go.  In that case, the Cubs have two options to fill center field.  One is Albert Almora, a 22-year-old who was the Cubs’ first-round draft pick in 2012.  As a contact hitter who rarely walks and only has a touch of power, Almora would be an offensive downgrade compared to Fowler.  On the other hand, he can make up some of that gap with superior glovework.  The other center field option is Jason Heyward, who has seven years remaining on his contract.  Heyward was slated for center field when the Cubs originally signed him, so it’s a possibility despite his limited exposure at the position.  He did just win a Gold Glove as a right fielder.  However, after a disastrous year at the plate, Heyward will spent the winter working on his swing, and the Cubs may not want to ask him to change positions as well.

Will Heyward’s massive contract lock him into a starting job for most of 2017, as it did this year?  I expect the 27-year-old to break camp as a lineup regular, but Maddon did show a willingness to bench Heyward in the playoffs.  Look for a shorter leash in Heyward’s second Cubs season.  Zobrist, also signed as a free agent in the 2015-16 offseason, remains slated for regular playing time.  He began 2016 as the Cubs’ regular second baseman, but the emergence of Baez has pushed him to left field.

So a Zobrist-Almora-Heyward alignment seems pretty good, right?  The “problem” is that the Cubs also have one of the game’s best young hitters, Kyle Schwarber.  Schwarber, 24 in March, made a surprisingly fast recovery from his early-season torn ACL and LCL, serving as the Cubs’ designated hitter in the World Series.  Can Schwarber catch again, alleviating some of the outfield logjam?  Even Hoyer doesn’t seem to have the answer yet, plus there’s just not a big need for him behind the dish.  Save for 10 interleague games in American League parks, Schwarber will need to get most of his playing time as the Cubs’ left fielder.  The need to get Schwarber into the lineup creates urgency for Heyward to bounce back offensively, as Zobrist could wind up in right field when Schwarber plays.

If the Cubs will have to do some juggling to get Schwarber, Heyward, and Zobrist enough at-bats, they’ll really have a problem finding room for Jorge Soler.  Soler, 25 in February, is the Cubs’ most obvious piece of trade bait.  The Cubs control Soler for the next four seasons.  In 765 career plate-appearances, he’s hitting .258/.328/.434.  In 86 games this year, Soler showed increased power and patience at the plate, but he’s still only a slightly above average hitter.  He’s also pretty clearly a below-average defender and has been injury-prone in his career.  Nonetheless, Soler’s ceiling may still tantalize some teams, as the former top prospect’s bat still has All-Star potential.  In potential trades with the Rays, White Sox, Phillies, and others, the Cubs could attempt to acquire a controllable starting pitcher and/or reliever for a package centered around Soler.

Once free agency starts to die down in the new year, the Cubs may want to look into a few contract extension opportunities.  Hendricks and Schwarber could be candidates.  Bryant and Russell would certainly be of interest, though they’re represented by Scott Boras.  There’s also the looming free agency of Arrieta, who turns 31 in March.  The 2015 Cy Young winner picked up where he left off in 2016, posting a 1.74 ERA through his first 14 starts.  Even in that period, however, his command had begun to falter, and in the 126 2/3 innings that followed (including the playoffs), Arrieta posted a 4.19 ERA, 8.1 K/9, 3.7 BB/9, and 1.14 HR/9.  That performance is more in line with a Matt Moore, Ian Kennedy, or Trevor Bauer.  Good, but not $30MM per year good.  With a potential $105MM owed to Lester through 2021, a mega-deal for Arrieta looks a lot less appealing than it did a year ago.  After 2017, Arrieta may be joined in free agency by Yu Darvish, Johnny Cueto, Danny Duffy, Masahiro Tanaka, and others, so it’s quite possible the Cubs explore alternatives.

The Cubs had baseball’s best group of position players in 2016.  Even if they subtract Fowler and Soler, full seasons from Schwarber, Baez, and Contreras, plus some level of bounceback from Heyward, might result in an even stronger group in 2017.  Likewise, the Cubs are looking to improve upon an already-strong starting rotation.  While the bullpen needs significant retooling, the Cubs project to have a good $25MM+ in the war chest to spend on new player salaries for 2017.  The team is in an incredible position for years to come, suggesting 2016 was just the beginning.