There were a million ways the Brewers could have screwed up last offseason

When the Milwaukee Brewers won the National League Central, my first reaction was to laud their offseason. Specifically, it was worth lauding their decision to go all-in and spend money this winter because it was much trendier to hoard cash and ignore free agents. I was not alone in this take, and that’s because there’s a direct correlation between their aggressiveness and the wafer-thin margin between them and the Cubs. The Brewers tried, other teams poked around and stood pat, and the Brewers won. It’s not complicated.

What I would like to do today, however, is go back to the forks in the road. The offseason isn’t just a matter of going down to the ol’ baseball player store and getting a pallet of baseball players. The free agents have to want to come to that city. They have to be convinced. They have to fit within a budget. Other players come on the trade market unexpectedly, and a team’s attention might need to shift away from the free-agent market. There are so many different threads to tug on, so many forks in the road.

Let’s say, for the sake of argument, that the Royals signed Lorenzo Cain to an extension three years ago. They were flush with World Series cash, and their front office highlighted him as a player who would age well.

Where would the Brewers have allocated the millions they gave to Cain? How entirely different would their offseason had been? Was there a way that a go-for-it attitude might have been a spectacular failure?

Oh, buddy. Always. There are always great ways for teams to waste money.

Start with what everybody expected the Brewers to do: buy starting pitching. When I previewed the teams that had a chance to dominate the winter meetings, I guessed the Brewers would be one of them because they had a young, inexpensive team and money to spend. But I was way off when I figured they would help their rotation.

All they need now is pitching, and they’re so danged close. Zach Davies is solid, and Chase Anderson might be more than that. They were so close to having a low-cost, productive troika for the next few years, but Jimmy Nelson’s shoulder is done busted, and you can’t just swap tendons out of those things. They have solid starting prospects in the upper minors if they need depth, but they can really, really use another reliable pitcher in the rotation.

The one thing they didn’t need was another outfielder. Pitching, pitching, pitching.

They got Jhoulys Chacin.

That part was underwhelming! Sincerely underwhelming. While Chacin was sneakily one of the better pitchers on the market according to his 2017 WAR, it was not the big-ticket ace that some people expected the Brewers to go after.

Just imagine what would have happened if the Brewers did what we expected, though. Imagine, for example, that they signed Yu Darvish.

A fine idea! Even after the World Series meltdown, Darvish was a top-tier pitcher, someone you could put at or near the top of any rotation. The Brewers were surely at least a little interested.

He was also about to bust into a hundred pieces, as pitchers tend to do. Darvish made eight rough starts for the Cubs before going on the DL with elbow pain (a stress reaction that would eventually end his season). Now, the Brewers weren’t going to outspend the Cubs, but pretend that Darvish liked the idea of being the obvious ace on a contender instead of just another ace in the crowd. Or pretend that he grew up watching Laverne and Shirley, and that he has a lifelong phobia of pizzas that are the size of a Vespa tire. Whatever it takes, pretend that he went to the Brewers and offered his services at a substantial discount.

Say, five years, $80 million. Which is a year and $46 million than he eventually got. Which is also exactly what the Brewers spent on Cain.

Lorenzo Cain’s seven-win season would have turned into a zero-win season, and the Cardinals would have faced off against the Rockies for the National League Wild Card. That’s how easy the Brewers offseason could have been a disaster.

Well, sure, if you pick the worst possible outcome with an injured free agent, it looks bad. But not every free agent pitcher was a disaster. We won’t even get into Lance Lynn and Alex Cobb — I was kind of thinking the Brewers should sign both — and skip right to Jake Arrieta, who had a solid season. He wasn’t a Cy Young winner, and he probably never will be again, but he was worth three wins above replacement according to Baseball-Reference. That’s a full win better than any of the starting pitchers on the Brewers. He would have been expected to be the undisputed ace, and by gum, he would have been.

Except Lorenzo Cain’s seven-win season now would have turned into a three-win season, and the Brewers probably would have faced off against the Rockies for the National League Wild Card. While they swept the Rockies in the NLDS, things could have been different in Wild Card Game. At the very least, we could all agree that they would be a weaker team for the NLCS without Cain.

Now forget about the free agents and look toward the trade market. Let’s say the Brewers’ entire reasoning for signing Cain was to use their center field prospects (Brett Phillips, Lewis Brinson) in a trade package for a starting pitcher. Let’s say they could have talked the Rays out of Chris Archer, or the Tigers out of Michael Fulmer. They would have been measurably worse, even as they tried to improve their team in an obvious, proactive fashion.

Even if they took the prospects they swapped for Christian Yelich and dealt them straight up for Gerrit Cole, they would have been worse off. Even with an ace, they probably wouldn’t have challenged the Cubs for the division on that last day. That’s just how good Yelich was.

It all speaks to the success of the 2018 Brewers. It took a good plan. It took a good execution. And it took at least a little providence from the baseball gods, because I’m sure their October whiteboard had all sorts of different options on it. There were a lot of different ways the Brewers could have entered March confident that they had built a legitimate contender. There were a lot of different ways they could have been wrong.

They chose wisely. They doubled down on the outfielders, fully aware that Christian Yelich’s left-handed stroke was perfect for Miller Park. They saw depth in the lineup, on the bench, and, perhaps most importantly, in the bullpen as the ways they would help make up for their lack of a true ace (or even no. 2). And they were right.

At some point, though, it probably would have been possible to tempt them down a different path. I’m sure I would have written a column titled, “The Brewers won the hell out of the offseason” if they had signed Lynn and Cobb and traded for Archer. Everyone would have agreed it was a brilliant winter for Milwaukee.

Instead, they navigated the minefield expertly, as if they had the benefit of hindsight. Their offseason plan didn’t have to work this smoothly, and there’s probably a cautionary tale in here for the next team that pounces on the offseason. All we know is that it sure worked for the Brewers, and they’re four wins away from the World Series because of it.

It was a more impressive magic trick than you think.