Chicago Cubs: What will next year’s roster look like?

After another disappointing September finish, the Chicago Cubs again find themselves looking for answers and fixes on their  talented ball club.

One of the more difficult exercises when analyzing the 2019 Chicago Cubs (and trying to ascertain strengths and weaknesses), is looking at the stats and trying to figure out how this team could have struggled this badly at times.

When you look through the hitters, it’s tough to find guys who played significant time who grossly underperformed. When you look at the pitchers, there’s a bit more regression, but certainly the stats do not tell the whole story. Heck, even the run differential doesn’t jive with a team that was mediocre.

That being said, the team as a whole underperformed and lost more games than they should have, more games than the organization wanted to, and certainly more than the fans wanted to see. What does that mean after the “year of reckoning” promised by Theo Epstein after a miserable end to the 2018 season? It means change. Maybe not as much as some think, but it’s coming.

What kind of change is anyone’s guess, quite frankly. However, what we do know is that there will be a new manager with the departure of the best Cubs’ manager in my lifetime, Joe Maddon. There are also a ton of decisions that need to be made with respect to free agents, options, positions, and philosophy. While there won’t be any kind of huge teardown with the pieces the Cubs still have in place, it’s possible (or even likely, depending on who you ask) that a really solid player could be jettisoned in hopes of a better fit coming back in trade.

Still more than five months away from meaningful Cubs baseball, let’s try and sort out what might be on the field in 2020.

Chicago Cubs: What are the chances someone here gets traded?

You could make a case for any of the players pictured above being traded this offseason, and many already have. Former MVP Kris Bryant, who many think won’t sign an extension and won’t be brought back after 2021, has been the subject of numerous trade ideas so far.

Fiery backstop Willson Contreras has also been brought up because of his potential and also his lack of pitch-framing ability as compared to Victor Caratini. Once-beloved defensive specialist Albert Almora has fallen from grace and doesn’t even seem to be a great defender at times anymore after a huge gaffe in a crucial moment down the stretch for the Cubs.

Less likely to be traded are Jason Heyward, who no one probably wants at $23.5 million for next year (and beyond) and Javier Baez, who is probably the most coveted of the Cubs assets because of his offensive, defensive, and intangible potential. While Heyward would be tough to shop without eating a ton of money, Baez could be shopped for a return haul, but it would leave a huge hole in the middle of the infield.

There is also the possibility that Ian Happ might get shopped, although it’s unclear how much other clubs would be willing to send back for a guy who spent most of the season at AAA and then came back and raked in the last month of the season. Happ has a ton of potential and could blossom given a full season of time somewhere, but teams may be hesitant to give up much for a guy who doesn’t have a real position and has been inconsistent so far in the majors.

If the Cubs wanted to go the Gerrit Cole or Stephen Strasburg route, you could also see them shop Jose Quintana after picking up his option. If anyone would be interested in Tyler Chatwood as a starter, he could be traded as well, but it’s doubtful anyone would take that risk without the Cubs eating some of his $13 million salary.

With every player technically available at the right cost, who might be someone the Cubs would target in the offseason in exchange for some of the guys listed above?

Chicago Cubs: Remember this guy?

The Cubs have two major holes on their roster: a legitimate leadoff hitter and a bona fide ace. If I were Theo Epstein, these would be my areas of concentration this offseason. While there aren’t a ton of those prototypical high OBP/runs well leadoff guys in baseball at all, there are some who the Cubs might be able to pry away from their current teams via trade this offseason. Problem is, they’re also some of the best players in baseball and fans will not like how much they cost in return.

Mookie Betts of the Red Sox and Francisco Lindor of the Indians are two players who seem to be in the same boat as Bryant. While they are phenomenal players any team would want on their roster, they also are going to command a ton of money on the free market in short order and their respective teams may not be willing to spend that kind of money.

If the Cubs are serious about getting back to the World Series, they need to go after one of these two guys. Putting a Betts or Lindor at the top of the lineup automatically makes our lineup one of the best and deepest in baseball. The best part is that both guys are also great defenders and just about to hit their prime. The downside: we wouldn’t have them for very long unless we could work out a very expensive extension.

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Gerrit Cole would do the same thing for the Cubs rotation that a Lindor or Betts would do for the lineup it would instantly make everyone better and push everyone down a slot. Instead of going into the season with Kyle Hendricks as your “ace,” he would now be your second-best starter. That would push Yu Darvish to third in the rotation and Jon Lester fourth.

Even taking into account his diminishing returns and age, any rotation with Lester as your fourth best starter is a monster. While he’s not the guy he was five years ago, he’s still capable of spinning a gem any time he goes out there.

Bringing in a guy like Cole might be just the kind of jumpstart the entire staff needs to bring their “A” game every night. Ditto for Strasburg if the Cubs decide to go that way.

If they don’t go for a big splash, contact will be the order of the game on the offensive side, with a veteran presence prefered. Someone like Howie Kendrick might be targeted, although if Ben Zobrist were to want a cheap swan song, I’m sure the Cubs would consider it from a guy who is the ultimate contact/OBP presence.