These 4 Landmarks Will Let You Track Progress of Cubs Rebuild

The ubiquity of GPS has made maps a thing of the past, but I’m relatively sure most of you reading this came of age at a time when Rand McNally road atlases were a staple of every car used for more than a daily commute. And raise your hand if you or your parents ever used a AAA TripTik for a long drive. We had one for our journey west to Yellowstone when I was a kid and it seemed like the coolest thing in the world because you drove the route on the given panel and then flipped the page to the next leg of the journey.

Technology has blunted my sense of direction like Snoop Dogg, but I do still enjoy the concept of establishing landmarks to track the passage of time and distance. It could be specific cities or just estimated stops for gas and food, but I find it comforting and even a little nostalgic. I also enjoy watching the ETA drop as I’m able to cruise along faster than the speed limit.

My coverage of the team’s current state has been a wee bit more on the critical side lately, and for good reason, but no amount of bitching from me is going to convince Jed Hoyer to get into the passing lane or take the shorter route over the one he’s chosen. With all that in mind, I wanted to take a slightly more agnostic look at the Cubs’ road back to being competitive.

Of course, I’m oversimplifying things to a great degree here because operating a professional baseball organization is fraught with more uncertainty than making a road trip. It’s not like cities can just move around on the map or disappear entirely, nor can you fire a member of your family halfway to the destination. Or can you?

Rather than telling us anything for certain, the four events below will give us an idea of where the Cubs are in their own journey and how quickly they should arrive at what we all hope will be winning baseball.

2022 Draft

This year’s draft is being held from July 17-19 and the Cubs have the seventh overall pick, which is a really nice spot for them because it looks like they’ll have some solid options. The consensus among recent mocks is that the Cubs will select either prep shortstop Termarr Johnson or juco third baseman Cam Collier, both of whom have received rave reviews for their hit tools.

Thing is, they’re both teenagers who will take time to develop. That is a decidedly different strategy from the one the Cubs employed during the rebuild that started a decade ago when they explicitly targeted college hitters who could advance through the ranks quickly. Rather than looking to jumpstart development, this would be more about backfilling a system that is already seeing several position players forcing their way up through the lower levels.

There is, however, another wrinkle that Keith Law noted in his mock draft back in May. He had the Cubs taking Collier and said their pick was “more likely a college bat,” noting that they’ve also been linked to Campbell University shortstop Zach Neto (who Law had at No. 17 to the Reds). That’s a little funny because Collier graduated high school early to get in a year of college rather than playing prep ball, kind of like Bryce Harper, and is actually younger than Johnson.

Neto is a contact hitter who scouts believe might be able to stay at short, though a move to second or third is possible. The real key here is that we’re still talking about his hit tool as his carrying trait, so that tracks with the other possibilities. Unless the Cubs reach for stud righty Dylan Lesko, the top pitcher in the class until undergoing Tommy John in April, the road seems pretty clear.

Selecting Neto, who is more than three years older than either Collier or Johnson, would perhaps indicate a desire to compete sooner. Going with Lesko would signal a much higher risk tolerance than the Cubs have had for pitchers in the past, which is good, but it also means they’re not planning for him to make an impact in the next few years.

This is kind of like a lunch break on the trip.

Trade deadline

Here’s where we will really start to understand how long this drive is going to take, as another major selloff sets things back like a flat tire. Moving Willson Contreras and/or members of the starting rotation is as clear a sign as any that the ETA for arrival in Competitiveville is 2024 at the earliest. You can talk about Kyle Hendricks no longer being an ace or Marcus Stroman not being what people had hoped for, but those pitchers would still need to be replaced.

That takes money, a lot of it. Competent MLB starters don’t exactly grow on trees and the Cubs aren’t likely to suddenly turn the rotation over to a group of rookies and young veterans. Is it possible they could make something work by doing that? Sure, but moving current starters means the front office is comfortable with potentially punting another season.

We know there will likely be several relievers traded because that’s the only way to get value from guys on one-year deals, same for Wade Miley and Drew Smyly if either of them manages to be off the IL by August 2. That was all part of the plan though. Moving pitchers who are still under contract beyond this year is a different story.

Contreras is also on an expiring contract and his exit has seemed inevitable for more than a year now, but his departure would be much more significant than someone who was signed almost with the intent of being flipped. A clubhouse leader and longtime member of the team, he’s an elite offensive producer whose contributions can’t be easily replaced.

There are worse options than giving the keys to Yan Gomes and P.J. Higgins, maybe with Miguel Amaya riding along as he works toward his learner’s permit, but that’s not really a duo you’d expect a contender to employ. Speaking of Amaya, he’s had only 106 professional plate appearances since 2019 — all at Double-A — and will be coming back from elbow reconstruction.

If the Cubs somehow manage to extend Contreras (unlikely) and they also keep both Stroman and Hendricks, this is more or less a stop for gas. But if two or more of those guys are gone, we’re looking at a radiator leak on a Sunday when every repair shop in this roadside town is closed. That would delay the trip quite a bit.

Free agency

This is the biggest one of all, like crossing the border into your destination state. If the Cubs actually make good on the promises to spend available resources by landing an elite shortstop, a starting pitcher, and some left-handed power, all the other detours may be forgotten.

There are already rumors that they’ll pursue one of Carlos Correa, Trea Turner, or Xander Bogaerts — which I’ll believe when it happens — this winter, the result of which would be immediate legitimacy. Mind you, I’m not saying the Cubs will become winners just from one deal. But like Jon Lester in 2015, it’s a very obvious sign that they’re going for it.

Getting payroll back to around $200 million and supplementing their young up-and-comers with proven veterans puts the Cubs back in the conversation regardless of what happens with the first two items. However, taking more half-measures and opting to wait in the wings to find value with mid-level signings means the ’23 season will again be one of mediocrity.

2023 Draft

This is more like a potential detour in the event that the previous stops don’t get the Cubs where they need to go because we’ll probably already know where they’re headed by this point. But this isn’t so much about the draft itself as it is where the Cubs will end up picking because it’ll be the first draft to feature the new lottery system that determines the first six picks.

The three worst teams in MLB all have a 16.5% chance at the top pick, with incremental drops from there. The Cubs currently have the fifth-worst record, giving them 10% odds at the top pick, but they’re only 1.5 games behind the Reds for the top three. A team that pays into revenue sharing can’t have two lottery picks in a row, so the Cubs falling into one of those top six picks would eliminate most or all of the impetus for tanking again next season.

Even if they finish among the worst teams in the league, it’s entirely possible that six others win the lottery and push them to the seventh pick or even later. That could mean another uncompetitive season because they haven’t exhausted their lottery pick. Of course, they’d be playing with fire in that case because attendance is already flagging and people aren’t showing up to see their team play like it’s trying to land a No. 1 pick.

Imagine dad deciding to take country roads right when you’re almost at the destination, only to find the road washed out by a mudslide or rockfall. That’s the worst-case scenario here, though it could be very different if the Cubs manage to land a prime selection.

In that case, we could be talking about money in the bank. I mean, think about how great it would be for them to get a top-three pick and then go big in free agency with the knowledge that they’ve set themselves up much better for the future.

There will be plenty of other little mile markers and scenic points along the way, but I think the four events above will tell us all we need to know. Bon voyage.