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The 3 toughest decisions of the MLB trade deadline

The Twins and Brewers are ahead of schedule, and the Royals are in limbo. What should they do?

Minnesota Twins v Milwaukee Brewers Photo by Dylan Buell/Getty Images

DAD: See, Jimmy, when a baseball team wins games and loves their season very much, they become buyers.

JIMMY: [playing video games]

DAD: And when that team loses their games and is forced to confront their worthless existence, they become sellers.

JIMMY: It’s not that simple. Nothing you tell me in that voice is. There are always complications, gray areas, blurred lines. Life is a series of blurred lines that people attempt to understand as if they’re high-definition lines, unambiguous and easily defined. I worry that you’re feeding me platitudes because you underestimate my intelligence.

DAD: God, I’m glad you don’t actually share any of my DNA.

JIMMY: What?

DAD: Good talk about baseball, son.


It never is that simple. There should be buyers on one side and sellers on the other side, but it’s those gray areas and blurred lines that mess everything up. We’ve looked at how the second wild card messes the trade deadline up, but this is different. We’re not even talking about the second wild card this year because the divisional races are such a mess.

There are three teams with impossible decisions to make at the deadline. There are a dozen with hard decisions, sure, but these these three are caught between their plans for the present and their plans for the future. Do they buy? How aggressively do they buy? What kind of prospects do they trade? Do they cross their fingers extra hard and hope everything works out?

Here are those impossible decisions.

Milwaukee Brewers

Nobody predicted the Brewers would be any good this year. Nobody gave them a chance or thought they were ... oh, hold on, let me just rustle around this knapsack and PULL OUT THESE HOT TAKES FROM FEBRUARY:

Most underrated lineup in baseball: Milwaukee Brewers

Darn straight.

Except this is a lineup with purpose. Ryan Braun is getting older, but he’s still the known quantity, and he’s surrounded by players who make sense.

Heck yeah.

Most underrated rotation: Toronto Blue Jays

Wait, back up, you went too far.

It’s not a lineup that needs Eric Thames to hit 40 homers just to be functional, in other words. It’s a lineup with a lot of variables and a high ceiling. Of all the lineups in baseball, this is the one that seems like it would be the easiest to justify retroactively in August if the Brewers are doing better than expected. Of course they’re a strong lineup, we’ll think. It was so obvious the whole time.

And now Thames just might hit 40 homers. Travis Shaw is looking like the steal of the offseason. Domingo Santana and Orlando Arcia are coming into their own, and it’s beautiful to see. Back in March, I mentioned the Brewers were a couple good pitchers away from being sneaky threats to the Cubs. And look at them now: 3½ games ahead of the Cubs.

They’re still at least one good pitcher away from being sneaky threats to the Cubs. I know, I know, they’re still in first, but that rotation is held together with twine and tree sap, and the goal should be to nab a pitcher who could be around for a couple years, someone who isn’t a rental.

Except those guys are expensive. The A’s aren’t going to donate Sonny Gray to the Brewers in a show of small-market solidarity. The most effective trade the Brewers could make would also be the one that would force them to rewrite their rebuilding plans on the fly. Which is fine, contending happens, and it’s a gift! But the Brewers have done too much work to build the farm system to get cavalier about dealing prospects.

Maybe a couple rentals, then? Hang on to the keyest of the key youngsters, and deal from the depth that runs through the middle of their top-30 list?

They’ll make trades. It’s the scale of those trades that’s in question. The Brewers don’t know if they should go all-in, mostly in, or somewhat-in, and I don’t blame them.

Minnesota Twins

Same dilemma as the Brewers — call it comingoutofnowhereitis — with a little bit of a twist. The Twins are 47-45, good for second place in the AL Central. They’re half-a-game back of a wild card. They have Miguel Sano blossoming into a star and a lineup filled with capable, solid hitters. They were building to something, and it’s possible that they just arrived a year or two early, and they should go all in.

Except, at the risk of being the new-orthodoxy pedant in the house, the Twins are 40-52 if you look at their expected record based on runs scored and runs allowed. Normally, I’m keen to look at the problem pitchers who were removed, or the hitters who have already lost their jobs, and figure that the overperformance has actually helped them make moves with a little urgency, which makes their continued contention something of a self-fulfilled prophecy.

But the Twins haven’t made those moves yet. They’re sticking with Kyle Gibson because they haven’t figured out how to replace him. They’ll stick with Hector Santiago when he gets back because they haven’t figured out how to replace him. Byron Buxton, Jorge Polanco, and Jason Castro are going to continue being offensive drags because the alternatives are just as unappealing.

Now they have to figure out if a) they’re as good as their just-over-.500 record, b) the Indians are as bad as their just-over-.500 record, and c) if this is the time to make a huge deal, a complementary deal, or stand pat. The Twins would enjoy the services of Sonny Gray for the next couple years. They would have to be super convinced that they have the true talent of a contending team, though. I’m not so sure.

Kansas City Royals

Ah, a different dynamic. The Royals aren’t new to this scene. They’ve contended before. They’ve won before. They’ve made savvy trades and ridden them all the way to the World Series. The question is if it makes sense for them to do it one more time.

Like the Twins, the Royals are outperforming their Pythagorean record — 42-49, which is a boost of three wins. Like the Twins, they have some obvious holes that they’ve tried to patch internally, with little success.

Unlike the Twins, the Royals aren’t set up particularly well for the future. They’re going to lose at least two or three of their core players to free agency, and that’s if they don’t lose five or six of them. The extra money from winning the World Series is gone. Jorge Soler, a young player they added in the hopes of reversing some of that, was just demoted to the minors. The small-market reaper is coming for them, as the prophecies foretold. If they’re going to avoid the imminent decline, they’ll need a lot of help from their farm system to fill in the gaps, especially in the rotation. That’s one strategy: Keep who you can, and supplement the roster with low-cost organizational options.

The other strategy: Realize this might be the last run for the Moustakas-Hosmer-Cain core, and trade some of those organizational options for win-now players. The Royals are interested in Lance Lynn, perhaps. Good. That’s the kind of rental they should get to bolster their chances at one last run.

Except, hold on, waaaaait a second, what if they sign two of those aging free agents (say, Moustakas and Cain) and develop some players around them (including the prospects they would have traded for Lynn). Isn’t that sustainable?

Could be. But they also might go five years without being within three games of first place in July. Just ask a Royals fan. They went nearly two decades. There’s something to be said about a team that’s raised expectations like the Royals giving their fans one last ride on the roller coaster. This is a familiar group. The fans like them. A summer of reinforcements seems like it would be better for the Royals’ burgeoning brand than a summer of sell-offs.

Even if those sell-offs could lead to the kind of young, sustainable core that got the Royals where they are in the first place.

What a mess.

For my money, I’ll go hard buy for the Brewers (the Sonny Grays of the world, because they’ll be contending indefinitely), soft buy for the Twins (only the cheapest of the cheap options, because Bartolo Colon will fix everything), and rentals-or-bust for the Royals (there’s nothing they can probably do for the next couple years, so live it up now.)

But I’m glad I’m not the GMs or owners of these three teams. All 30 teams will face tough decisions at some point this deadline. These three will have tougher decisions than most.