How should the Cubs address the leadoff hitter issue when there are no clear-cut upgrades available in free agency and few prototypical leadoff hitters in the game at all? Trade?
-- @dennisr04010724 via Twitter

Mookie Betts or Whit Merrifield sure would look good in a Cubs uniform, don't you think?

We obviously can't see the full picture of what Chicago's roster will look like for 2020, and there's a chance the Cubs shake some things up via trade in the coming months. For the top of the order, I do think the most likely path to a solution is through the trade market, but not strictly in a trade-for-a-leadoff-man way.

What I mean is that the Cubs are more likely to target hitters who can help reshape the makeup of the offense. Consistent contact and the ability to hit offspeed pitching would be areas to tighten up, for example. And if some of the current roster is turned over through trades, perhaps the Cubs will home in on a big-ticket free agent or two.

Once the dust settles on the offseason moves, and the Cubs can look at their offense as a whole, then it will probably be time to identify the best options at leadoff. Consider what president of baseball operations Theo Epstein said recently about addressing the No. 1 spot in the lineup:

"If we can acquire a prototypical leadoff hitter, that'd be fantastic and make everybody's life easier going forward. If we can't, the best solution is just get as many players who get on base as possible and have a lot of different options of guys that you can throw up -- based on matchup situations -- into that spot. But, I think we have to do a better job of having more diverse offensive skillsets, including players who specialize in getting on base. If they can be a great baserunner, all the better."

Epstein called the 2019 statistics out of the leadoff spot "unacceptable," and they were. The Cubs cycled through 11 players atop the order (counting starts only) and they hit a collective .212/.294/.383. One year earlier, Chicago used 10 players in the No. 1 slot and they combined for a .302/.366/.454 showing. So, what happened?

Two years ago, the Cubs found a nice one-two combo between Ben Zobrist (vs. righties) and Albert Almora Jr. (vs. lefties). This past season, Zobrist was gone for four months in the middle of the season and Almora's production against southpaws dropped dramatically (.213/.254/.278 in '19 compared to .295/.340/.402 in '18). That set the downward spiral at the top in motion.

This winter, Zobrist is a free agent and retirement is a possible outcome. Almora is under team control and eligible for arbitration, but the center fielder looks like a trade candidate. I'm not sure that the Cubs' main leadoff man in 2020 is currently on the team's roster. Maybe rookie Nico Hoerner will earn that role by the end of the year, but I'd expect Chicago to lengthen out its lineup this winter to find other options.

"If you set out as a goal to lead the league in on-base percentage," Epstein said, "you're usually not going to be wanting in the leadoff spot. So, I'd rather keep that goal of just, one through eight, finding guys who get on base and it should take care of itself."

With a little bit of time and perspective, how would you prioritize personnel needs heading into the winter? It feels like adding another impact starter has shot up the list, given lackluster performances from José Quintana and Jon Lester.
-- Matthew W.

I would agree that adding an impact arm for the rotation tops the to-do list for this winter for the Cubs. Cole Hamels is hitting free agency, Lester is not getting any younger and Quintana -- while I think it makes complete sense to pick up his $10.5 million team option for '20 -- looks like a No. 4 or No. 5 starter right now. Even factoring in Yu Darvish and Kyle Hendricks, the Cubs' starting staff needs a little more length.

Maybe Tyler Chatwood's solid showing as a swing man in 2019 will mean good things for a move back to the rotation in '20, but should the Cubs count on that? Behind him, the top two internal options heading into next year would be Alec Mills and Adbert Alzolay. They might develop into solid starters, but should the Cubs also count on that happening next year, too?

After the rotation, the Cubs need to add at least one experience setup arm in front of closer Craig Kimbrel. Some younger options emerged this season, but Chicago needs insurance in case Kimbrel's rough campaign was more foreshadowing than fluke.

Then, the lineup needs help at the top (as noted above) and solving center field and second base will be critical. After his showing down the stretch, Hoerner looks like the favorite to land the job at second in the spring.

With how Darvish performed in the second half of 2019, should/would he be the 2020 Opening Day starter? Or, should it be Kyle Hendricks? Lester did not have a good season, but would he still be in the running?
-- @RizzoDarkThirty via Twitter

That'll be a fun topic to debate during Spring Training, especially after we know who else might be a part of the Cubs' 2020 rotation. You could make a case for all three of those starters to earn the Opening Day honor. Maybe Darvish is most deserving as the closest thing to an "ace" among the starters. Lester certainly has the stature to warrant the nod in the first game. Hendricks has been a leader by example and a source of consistency, and is signed for the next several years. I might lean towards Hendricks right now.

I can't recall a come-from-behind win this year (probably because the gut-punch losses are quite fresh). What was the Cubs' record in save situations this year vs. the performance of their opponents?
-- @RossIshikawa via Twitter

The Cubs had 28 blown saved in 61 opportunities, equating to a 54.1 save percentage in 2019. On the other side of the coin, teams had 19 blown saves in 65 chances against the Cubs (70.8 save percentage). While the tough losses obviously stick in your memory, the Cubs did have 34 come-from-behind wins this past season, including 14 wins in their last at-bat.

Do you see the Cubs talking to the a team like the Marlins for some of their young pitchers? Someone like Sandy Alcantara?
-- Greg K., Hartford, Wisc.

If you ran a team in the midst of a rebuild, would you easily part with a 24-year-old starting pitcher coming off a building-block season? I like the concept -- targeting young, controllable starting pitching -- but it's hard to envision Miami doing something like that unless there's a good prospect package headed its way. What the Cubs will need to do is find teams who are thin in an area where Chicago has a surplus, or a team that steps up as a big player for one of the Cubs' core guys in trade talks. That will be the likely recipe for addressing some of Chicago's needs.