Cubs’ Buy/Sell Decision Must Fall Much Earlier Than Trade Deadline

The Cubs recently went exactly one month between winning consecutive games and haven’t won three straight since late April. Another sign of that futility is that Shōta Imanaga‘s win on Sunday was the first recorded by a Cubs starter since Javier Assad on May 15 against the Braves, a stretch of 21 games. Speaking of Imanaga, his 11 walks are the fewest by any Cubs starter in his first 12 starts (since 1901) and his 72 strikeouts are fewer than only Kerry Wood (107 in 1998) and Mark Prior (86 in 2002).

Signing Imanaga to a deal worth about half of what had been projected was easily the Cubs’ best move of the offseason, and it would still be considered as much had they committed closer to nine figures. But the problem with a value-based approach that prizes “measured aggression” is that it requires perfect timing in order to be successful. Even with roughly 60% of the season remaining, it’s more than fair to say the Cubs didn’t do enough to improve the window for that timing.

One of my favorite mobile games is called Golf Clash, in which you take shots by pulling back your chosen ball based on its attributes and then let it go when a swinging directional arrow is in the middle. The higher the level and the worse the lie — rough, bunker, etc. — the faster the arrow moves. You also have to play the wind, which has a tremendous effect on the ball when it’s in the air.

As I watch the Cubs this season, I can’t help but think about Jed Hoyer and Carter Hawkins shanking some of their moves to the left or right and failing to account for swilling winds that guide their shots astray. In some cases, it may be a matter of going with a basic ball rather than paying more for a specialty option with better attributes.

That latter analogy can be applied directly to the bullpen, a unit Hoyer hinted could be bolstered by buying a measure of “certainty” in the form of multiyear deals. For whatever reason, whether it was prices falling outside what their algorithm said was acceptable or a belief that Craig Counsell could Rumpelstiltskin straw into gold in the ‘pen, the Cubs entered the season with yet another cobbled-together collective that hasn’t found consistency.

Rather than rehash any number of points that have long since become old hat — like Christopher Morel being the worst defense third baseman by a pretty good margin, statistically speaking — I want to see if we can identify a point of no return for the front office. The trade deadline is July 30, but the Cubs can’t afford to wait that long to decide whether they’re buyers or sellers. Hell, they’re just one game removed from the cellar of the NL Central.

All the talk about trading for Vladimir Guerrero Jr. is fun, but the Blue Jays are in a similar spot and don’t figure to be pulling the eject lever too early. Improving their options at catcher and getting more support for the bullpen, however, are simpler additions that could boost competitiveness and set the stage for a bigger splash. To be clear, I’m still very skeptical of the club’s willingness to do what it takes to add Vladito.

Even though my opinion will probably remain there until something meaningful happens to change it, being five games over .500 by mid-July certainly makes a splashy deal more likely. As such, I see one soft deadline and then a firmer date ahead of July 30. The first is June 30, which sees the Cubs wrap up a seven-game road trip with three in Milwaukee.

Going 11-8 over the next 19 games and taking care of business against the Cardinals and Brewers could have the Cubs firmly in second place and holding onto a Wild Card spot. That makes an early foray into the trade market very possible, even likely, heading into July. From there, the All-Star Break provides another opportunity to assess the state of the organization. If the Cubs can survive three games in Baltimore and four in St. Louis, they’ll set themselves up nicely for the second half.

Hoyer and Hawkins didn’t do enough last winter to provide their team with enough margin for error, but they still have time to make improvements. They’ll need to move quickly though, and they may have to make the kind of choices that really hurt when it comes to giving up the prospects everyone wants to hug so tightly. It’s a difficult balance between present and future, one in which the front office has been holding its thumb on the latter plate for some time now.

Thing is, you can’t win for years to come if you don’t start winning at some point. Going seven years between postseason wins isn’t acceptable for this organization, so they’d best get to work over the next month to ensure we’re not still talking about their futility in 2025. And if they can’t make anything work or the key players on the roster continue to fall short, well, I guess they can start flipping veterans for prospects.

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