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Come Fan with UsSaturday, June 20, 2026

The win-now and win-later teams of the 2018 MLB season

Which teams around baseball are built to win now? Which are built to win later? Which are the Tigers?

League Championship Series - New York Yankees v Houston Astros - Game Seven
League Championship Series - New York Yankees v Houston Astros - Game Seven
Photo by Elsa/Getty Images

Not all contending teams are created equal.

This is a truism that has been around since the advent of baseball. Some baseball teams have older talented players making a lot of money. Some baseball teams have younger superstars who aren’t making much money at all. Some baseball teams have a combination of the two. And some baseball teams are talking to themselves in a very loud Ralph Wiggum voice.

It is our job today to figure out which teams are which. This is our annual post of the win-now windows around Major League Baseball.

While this post doesn’t use a scientific approach — I mean, screwing around in Photoshop is almost a science — I do look at the same criteria every year.

  1. See if a team’s contract situation is sustainable
  2. Look at the ages of their key contributors
  3. Check out how many of their prospects are major-league ready
  4. Put all of the above into a blender and whirrrrrrrrrr
  5. Drink your frothy analysis smoothie, it’s good for you

Mistakes were made last year. The Diamondbacks weren’t given enough credit, and the Twins certainly weren’t given enough credit. The Giants, Pirates, and Mariners were overrated, but in my defense, I always do that for those three teams.

This is the fifth year of the win-now window, and as you would imagine, things have changed quite a bit. In our first year, the Astros and Cubs were tucked in a little corner of their own, just waiting to suck. But they were going to suck with a purpose, and look at that, they are now among the class of baseball. The Phillies were just going to suck without a purpose, and they haven’t finished close to .500 since.

But the Phillies are also a good reminder you shouldn’t get too upset if your team is in the worst position. They should be watchable this year. They’re almost back. Every team is always, always, always three years away from contending. I call this the Gift of the 2003 Tigers, and I wrote about it to describe the future chances of the Astros. The three-year rule applies to every team in baseball, always. It applies to the Tigers right now. It will apply to the Giants when they fall into disrepair and sadness. It even applies to the Marlins, who can still make Derek Jeter and his Operation: Wolverine look absolutely genius.

But if you’re in that upper-left corner, it’s gonna be a long couple of years. Here are the win-now windows around baseball:

What I’m noticing: That top-right corner is extremely vacant. Gone are the days of the Yankees slapping a bunch of Brian McCann-type free agents on an aging roster. The Giants might have been closer to that corner with a healthy rotation, but for the most part, teams would rather be in the bottom left than the top right.

We wrote about that here. Please save all of the articles to Pocket or something.

Here is a more detailed description of each quadrant:

Win later

To be in this quadrant, a team will need to have some pieces in place for their next contending team. I’m not sure which prospects will break through for the White Sox — not yet, at least — but the Reds have already shared Luis Castillo with the world, and their lineup looks both promising and sustainable. The next time the Padres contend, Manuel Margot, Jose Pirela, and Eric Hosmer should be around, and that’s before you get to their thriving farm system.

For all the talk about tanking, there aren’t a lot of teams who are doing it perfectly at the moment. They’re just getting started. This quadrant isn’t as filled out as it used to be, mostly because the best rebuilding jobs have shifted to the right.

WIN NOW

Is this quadrant a relic? If the Giants somehow make it through their best starting pitchers getting raptured and contend for the NL West, will they be the last of a dying breed? It looks like it, at least until the next CBA fixes everything.

No idea

These are the teams with little hope for 2018 and, for the most part, a farm system that isn’t so hot. The White Sox sneak into this quadrant with a great farm system, but that’s only because they don’t have a Carlos Correa or Francisco Lindor-type player who is guaranteed to be a franchise cornerstone. Yet. Yoan Moncada might be that guy, but I’m gonna need to see some evidence of that first.

The optimistic outlook for these teams has to do with building a better farm through losing, and I can understand that. But at the risk of being a downer, I have to point out that teams don’t automatically have to snap out of whatever funk they’re in. Great farm systems don’t always turn into contending teams. There were a couple of decades where the Pirates continually squandered away first-round picks and kept screwing up. The Royals and Orioles had similar dry stretches. Just because a team picks early doesn’t mean they can avoid the Bubba Starlings of the world. Sometimes these teams pick them over and over again, and it’s not even through incompetence. Baseball’s a tricksy sport.

All of these teams have some sort of hope for the distant future, but it will be a long couple of years.

The teams that are here to stay

These are the Joneses. They have nicer cars than you. They make more money. Their kid isn’t “on probation” for “flaying small animals.” The only reason the teams in the bottom-right corner aren’t all stacked atop each other is because of legibility issues, but it’s not like I’m here to argue that the Yankees’ window is open wider than the Cubs’.

They’re all going to be around forever, and if you’re not already sick of them, you will be.

And they’re all going to Hawaii for Thanksgiving. Flying out extended relatives and everything.

Oh, you’ve never bēēn? You should go sometime.

The Mariners

There they exist until the end of time, stuck in the middle of the compass and doomed to repeat every season in an endless loop. Their logo is the compass, you see. This was a clue, something we should have divined from the baseball gods long ago. Their GM is stuck in a Greek myth where he tried to trade for Hera, and his punishment is to make 100 trades every season and get exactly nowhere.

Everyone else sort of floats around from year to year, though. We’ll see you next season for another installment. The best part is that at least one of these placements will be completely wrong, and we’ll get to laugh at us dummies back in the past who couldn’t see it coming. Good times.

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