This is the Year: Brewers Should Go All-In at MLB Trade Deadline

Back in May, when things were at their worst, I ironically wrote a piece about how lousy things were looking for the Brewers. Since then, they’ve turned things around, and although they fell one win short of their true goal of granting the city of Milwaukee free George Webb burgers, they now have 61 wins and are in a great position for the playoffs.

Despite the Cubs’ best efforts to reload in the offseason with Kyle Tucker and whatever clone of Pete Crow-Armstrong they’ve now molded into an MVP-caliber player, the Brewers have caught up. According to FanGraphs, Milwaukee entered Sunday with a 92.1% chance to make the postseason, but more importantly, they also held a 41.1% chance to win the division and a 25.1% chance to clinch a bye.

This is where the team ends up every year. They’ve become a perennial presence in the playoffs over the past several seasons, but seem to have one key weakness. And whatever that weakness is, invariably, it shows up glaringly in October. After losing in the 2018 NLCS to the Dodgers, the Brewers have won exactly two playoff games. Somehow, this is the same number of playoff wins as the Miami Marlins have over the same span.

So, with a few days left before the trade deadline, the front office faces a tough decision. They can do what they usually do and stay the course for the most part, making a few small moves to pick up an unorthodox reliever or platoon bat before being unceremoniously bounced in the first round of the postseason. Or, they can do what they rarely do and commit to the current roster. 

The latter option is far from an easy task. After all, there are few positions on the roster that are clear weaknesses and that have straightforward replacements available to be acquired. However, the good folks at Brewer Fanatic have already done the scouting work necessary to identify a few good options. In fact, Matthew Trueblood recently looked at 105 of them.

There are a few names that stand out on the list. Eugenio Suárez and Ryan O’Hearn could help fix the lineup’s current lack of corner infield pop, and O’Hearn in particular could lift a sagging first base tandem of Rhys Hoskins and Jake Bauers, both of whom are currently sidelined by injury. If the Brewers value positional flexibility, Willi Castro could be a great utility piece to help fill whatever gaps arise down the stretch. Of course, all three of these are rental players who would hit free agency at the end of the season, a characteristic to which Milwaukee’s front office is typically averse. This is the habit that should be broken this year. 

Risk aversion is a spectrum, but those who break no eggs make pretty crummy omelettes. It’s understandable to want to maximize value for money and prospects, but this season has been different. From starting the year by being beaten by the Yankees so badly it made torpedo bats a talking point, to going on an 11-game winning streak against tough competition, the Brewers have endured the valleys and are now ascending the peak. Despite its flaws and lack of any real superstars, this roster has shown resilience and the ability for anyone to step up on any given night and do what needs to be done to secure the win.

It’s clear that their usual trade deadline strategy works great for obtaining regular season wins, but it hasn’t yet led to any meaningful championship progress, so why not change it up? How does that saying go: the definition of insanity is not doing anything at the trade deadline despite having the ability to meaningfully upgrade what’s already a very competitive roster?

In a worst-case scenario, Milwaukee trades away a few of their Top-30 prospects and still makes their usual first-round exit. Would this constitute a failure? Maybe, but it would have probably been preceded by good decisions. After all, when is the last time the Brewers signed a bad free agent contract or got fleeced in a trade?

Baseball is an unpredictable sport. The more one tries to control the chaos, the more they tend to seal their own fate. For too long, it seems like the front office has tried to minimize risk. As a result, their potential upside has been inherently limited. So why not try taking a leap of faith? If it goes well, then great. If not, we’ll all grieve for a bit, then have a laugh about it and say we tried. After all, you know what they say: there’s always next year.