When Theo Epstein first took control of the Cubs operation, one thing he stressed was that they didn't want a short-term fix. Instead, what they wanted was to build the franchise from the ground up with the emphasis on a long window of contention. The thought process is that it's so hard to win the World Series, so a team needs as many chances as possible to get that done.
Man, how true.
The Cubs' window of contention has been open since they were a wild card team in 2015, and they got that elusive World Series title in 2016. They followed it up with an NLCS loss in 2017 and a Wild Card Game loss in 2018 (with a team that won 95 games).
Last season was a roller coaster. They started slow in the first two weeks but then looked like the 2016 squad for a stretch, winning 26 of their next 36 games. They'd be hot and cold for months afterward, mostly dictated by whether they were playing at the friendly confines of Wrigley Field or not. Through Aug. 8, the Cubs were 63-52 and had a 3 1/2 game lead in the NL Central. They were still in a wild card spot through mid-September, but completely melted down, losing nine games in a row.
Now, let's have a little perspective. While 2019 was obviously a disappointment, this is the first time since a stretch between 1967-72 the Cubs have had five straight .500+ seasons and that last span included zero playoff berths. This one had four, including three trips to the NLCS and a World Series title. This is still the Golden Era of Cubs baseball.
There remains a quality core here, but it's obvious changes need to be made to get back to a true World Series contender.
One big change has already been made, with David Ross taking over for Joe Maddon as manager. Let's look at what else might happen before the 2020 season starts.
2020 Payroll Situation
It's not great. Much like he did with the Red Sox, Epstein went bonkers with big deals and now ownership is balking at more giant-ticket signings.
- Guaranteed contracts (9 players): $134,460,000 (via Cot's Baseball Contracts)
- Estimated payroll with arbitration/pre-arb: $180,500,000 (via baseball-reference.com)
By all indications, with luxury tax and other fees, the Cubs are already on the hook for about $200 million for next season.
The Cubs have picked up options on Anthony Rizzo and Jose Quintana. The payroll last year was around $234 million by season's end, so there should be some wiggle room, especially with the Cubs' new TV network, Marquee Sports, getting set to launch. And yet, Cubs chairman Tom Ricketts doesn't sound like spending big is going to happen. He recently did a Chicago sports talk radio tour where he downplayed how much they can spend and instead emphasized building from within.
Biggest Needs
You can honestly make the argument the Cubs were the most talented team in the NL Central in 2019, but the players just didn't play well enough while the team also dealt with injuries and questionable bullpen usage. The mix just seems stale, though, right?
Right off the top, the Cubs likely need a fifth starter. Cole Hamels is gone. It's possible the Cubs entrust the role to Alec Mills or use an opener with Tyler Chatwood coming in relief, though, meaning they can avoid looking outside the organization for a starter. I'd still say they could use a depth signing at the very least, because Jon Lester is hitting his age-36 season and Yu Darvish has to be a health concern.
The offense could really use some stability and consistency, especially with someone who makes good contact. Back in September I hit on six drastic measures the Cubs could take and this is where two of them (trade Kris Bryant and sign Anthony Rendon or trade Willson Contreras and sign Yasmani Grandal) apply. Either of those moves brings more offensive consistency while also improving the defense -- at least in terms of framing with the latter.
The bullpen probably needs some rearranging, but it's arguable the personnel in house is all that is needed.
More than anything else, the players need to play better. It sounds so simple and probably a bit dull, but there's a lot of talent still on this roster.
Trade Chips
At this time last year, every big trade chip was a bit depressed other than Javier Baez and it would've been dumb to deal him. Right now, though, Bryant and Contreras should have great value on the open market and Epstein has noted that no one is untouchable. I'm sure he'd listen on Baez, but it seems like the best fit with the superstar shortstop is to explore an extension. Kyle Schwarber is coming off his best season and was a killer down the stretch (.304/.395/.663 with 16 homers and 45 RBI in his last 56 games), but I still don't think anyone values him like the Cubs do. The timing might be right on Ian Happ, too, after he hit .264/.333/.564 in 156 plate appearances after an extended stretch in Triple-A.
Addison Russell, on the flip side, likely has so little value that he should simply be non-tendered. Albert Almora should also be a non-tender possibility.
Possible Targets
As noted, something like Grandal with a Contreras trade or Rendon with a Bryant trade would make a lot of sense in both making the offense more consistent and helping to restock the upper levels of the minors. Bringing back Nicholas Castellanos also seems like something that's on the table.
Beyond that, however, I believe it's mostly going to be ancillary parts. Maybe a Kyle Gibson type for rotation depth, a bullpen arm like Drew Pomeranz would make sense and maybe a veteran bat (Howie Kendrick's name is a lot bigger than how much he'll fetch in free agency for obvious reasons).
Mostly, the Cubs' owners don't appear to be giving them the financial flexibility to make a huge splash this offseason to supplement what's a talented-yet-stale roster. Perhaps they are staying coy about things, though.
"As an organization, we're not talking about payroll or luxury tax at all," Epstein said, via cubs.com. "I feel like every time we've been at all specific, or even allowed people to make inferences from things we've said, it just puts us in a hole strategically. We'll see how things shake out at the end of the year."
It makes sense to take this stance regardless of whether they'll spend big or not. My guess is they won't unless they trade a lot of payroll. Keep those eyes on Bryant, first and foremost. If the Cubs are going to be players this offseason, my guess is that's attached to a Bryant trade.
