Watch Now: 2020 Cubs Preview: Last Hurrah For Cubs Big Three (1:31)

The golden age of Cubs baseball started in 2015 with 97 wins, a trip to the NLCS and all kinds of promise. It continued in 2016 with the franchise's first World Series title since 1908. There was a third-straight trip to the NLCS in 2017 (they had previously never been in even two straight) and then 95 wins and a wild card loss in 2018. But did that golden age end with the horrendous finish last season that saw them comfortably in playoff position on Sept. 5 before going 8-15 the rest of the way?

Well, 2020 will go a long way in providing us our answer. 

Ben Zobrist is gone. 

Jon Lester and Anthony Rizzo have club options for 2021 and if they aren't picked up.

Kris Bryant, Javier Baez and Kyle Schwarber are only controlled through 2021, Willson Contreras through 2022. 

Oh, and Joe Maddon is now in Anaheim. David Ross is now the Cubs' manager.

With some exceptions (like Kyle Hendricks and Jason Heyward), that's basically the entire core of the 2015-18 playoff teams. 

If 2020 goes well, one could envision extensions to some of the players listed above and the window of contention staying open for a little longer on the North Side. If it doesn't, a re-tooling is in order that could include letting Lester and Rizzo walk in addition to trading Bryant, Contreras and Schwarber (I don't think Baez ever plays elsewhere, however). 

All this said, yes, 2020 is a big year. How will new manager Ross handle it? Let's dive in. 

Win total projection, odds

  • 2020 Sportsline projection: 33-27
  • World Series odds (via William Hill Sportsbook): 20/1
  • 2019 record: 84-78

Projected lineup

  1. Kris Bryant, 3B
  2. Anthony Rizzo, 1B
  3. Javier Baez, SS
  4. Kyle Schwarber, LF
  5. Willson Contreras, C
  6. Ian Happ, CF
  7. David Bote, 2B
  8. Victor Caratini, DH
  9. Jason Heyward, RF

Bench: IF Nico Hoerner, IF Daniel Descalso, IF Jason Kipnis, OF Steven Souza, OF Albert Almora

We can really only be sure about the top five and Heyward here. There will be lots of rotating in and out, especially with the DH spot. Schwarber, Contreras and Souza figure to get looks there. Almora will get starts in center with Happ in left when Schwarber takes the DH. Bryant could also be kicked out to left with Bote at third and Kipnis at second. There are a ton of ways Ross can employ this lineup and several players have great defensive flexibility to help. 

Projected rotation

  1. Yu Darvish, RHP
  2. Kyle Hendricks, RHP
  3. Jon Lester, LHP
  4. Tyler Chatwood, RHP
  5. Alec Mills, RHP

Jose Quintana was slotted in the four spot, but he sliced his thumb open while doing the dishes. He'll miss the start of the season. 

Projected bullpen

They could sure use a good version of Kimbrel to settle things down here, no? 

From Grandpa to Boss

David Ross went out with a bang in 2016 as a player. He hit a home run in Game 7 of the World Series, helping the Cubs win a title and getting carried off the field. "Grandpa Rossy" became such a huge deal that he was on Dancing with the Stars. 

Now he's the boss. We've constantly heard refrains about "how can he manage his friends." We've also heard from actual Cubs players that, as a leader in the clubhouse, Ross was kind of a disciplinarian. Several players in spring training discussed how they got complacent under Maddon's hands-off approach in the clubhouse last season and that was their undoing in September. If that's the case, a change of voice was needed and Ross is a lot more hands-on in the clubhouse than Maddon was, at least from what I witnessed in Mesa in the spring. 

We can't be sure how well Ross manages games, but that's a question for all 30 teams in a 60-game season. 

A potentially loaded offense

There is a huge upside to the offense that was fifth in the NL in runs, fourth in OBP and fourth in slugging last year. Bryant, Baez and, to a lesser extent, Rizzo and Contreras have MVP upside with the bat, especially in short stretches. Oh, so does Schwarber. Yes, for real. In his last 56 games last season, he hit .304/.395/.663 with 16 homers and 45 RBI. 

That's potentially the most potent top five in a batting order in all of baseball. 

Happ ran a 126 OPS+ after returning from the minors and was killing the ball this spring while Caratini and Bote figure to be slightly above-average sticks as well. 

Finally, Heyward was hitting .290/.407/.480 in 31 games before Maddon moved him to the leadoff spot. Heyward hit .301/.363/.481 in 61 games after getting dropped in the lineup again. Is it possible it's as simple as just not leading Heyward off? 

There is some downside here, but not a lot. Expect the Cubs to be a prolific offense. 

Now, about that pitching ... 

Short season helps rotation?

At age 36, it appears the Hall of Very Good career of Jon Lester is on life support. He's definitely not an ace anymore and at times he's more like a fifth starter. It happens. Father Time is undefeated. The good news here is Lester doesn't have to be more than a No. 3 starter and also that the shortened season might be good news. He can unload the tank more and not worry about fatigue crushing him in the dog days of August. 

Darvish's first two years with the Cubs have been a mixed bag of injury and control issues. Well, until the second half of last season. After the All-Star break, Darvish had a 2.76 ERA with a ridiculous 118 strikeouts against just seven walks in 81 2/3 innings. With a shorter season, once Darvish is stretched out, expect him to go all out, velocity wise, and hammer opposing hitters with his full arsenal of 10 pitches. Still, there has to be some concern of regression to what he was in his first season-and-a-half. 

Hendricks has pretty well settled in as a very good mid-rotation type than the ace he was in 2016. And that's fine! But he needs to carry the load of a No. 1 or a No. 2 this season for the Cubs. 

Quintana was a below-average pitcher last season. He completely fell apart in September. In five starts, he had an 11.09 ERA and allowed 37 hits in 18 2/3 innings. He allowed opposing hitters to bat over .400 against him. Seriously. Meanwhile, in 36 innings over nine appearances -- including four starts -- last season, Mills pitched to a 2.75 ERA with 42 strikeouts and a 1.17 WHIP. It was a small sample, but he threw very well and this season will be a small sample. Mills was stellar in the spring, too, sporting a 0.84 ERA and 0.66 WHIP in 10 2/3 innings. Still, he's never proven to be great over the course of a full season and remains a question mark. 

And then there's Chatwood, who was an utter disaster in 2018, leading the majors with 95 walks in 103 2/3 innings. He was very good as a spot starter and reliever last season. Can he safely transition back to the rotation? He was looking stellar in the spring, but that's the spring and it was months ago. He's a big question mark. 

There's a path to the rotation being quality, but one could make the argument it falls apart and is among the worst in baseball. The answer generally lies in the middle, but this is just a 60-game season. 

Questions abound in bullpen

Kimbrel was atrocious last season after finally getting signed after the draft. Behind him are a series of question marks, too. Wick and Wieck looked great for the most part, but it was all small samples. Was Ryan smoke-and-mirror successful or was it real? Can Jeffress be effective again? Will we eventually see second-round pick Burl Carraway? How about top prospect Brailyn Marquez? He had 128 strikeouts in 103 2/3 innings last season, but that was in Class A. 

Losing Mills to the rotation hurts, too. 

Bullpens are taking on increased importance this season. How the Cubs volatile arms perform and how Ross uses them will ultimately shape the 2020 Cubs.