Cubs Rumors: Is it worth “going for it” this year as deadline approaches?

As the trade deadline approaches, should the Chicago Cubs make an aggressive push to “go for it” this year?

I thought it was an interesting discussion that the broadcasters had yesterday during one of the games against the Cincinnati Reds regarding whether 2020 is an appropriate year for teams in general. The Chicago Cubs, in particular, to “go for it” this year, meaning whether they should be aggressive at the trade deadline, which is tomorrow (August 31), to improve the team.

Despite their recent skid, the Cubs still have a reasonably comfortable advantage in the NL Central as we have passed the halfway point of the season. They are a flawed team, for sure, as their offense relies heavily on the three true outcomes, while the starting rotation has been up-and-down, and the bullpen, with Craig Kimbrel as the prime example, has been far from great.

Under normal circumstances, it would be a no-brainer that the Cubs should at least try to be aggressive at the trade deadline to see what is available and for what. However, the unique circumstances of this season lead us to wonder whether, as we near the trade season’s final hours, this is the right move.

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Given the team’s financial circumstances, plus the lack of depth in the farm system, the expectation is the Cubs will, at most, look to make small additions. Yet with the rest of the division under .500 and the Cubs the clear class of the division so far, perhaps they should go for it and try to make a big trade or two.

Some would argue that it’s not worth it because this season has less meaning than other seasons. On the other hand, some would say that this season has even more meaning because of all the adversity everyone has faced and that the season is so unique. It’s an interesting debate for sure.

Then there’s the playoff situation. Sixteen teams will get in, and the eventual champion will have to survive four rounds. It’s even more of a crapshoot than normal. Is it worth giving up part of the future or an otherwise valuable piece when the odds are so heavily against getting all the way through the postseason?

Underlying all this is the long-term health of the team. This may indeed be this core group’s “last dance” as many key players will be up for free agency — and big paydays — soon. Jim Deshaies even said during the broadcast that there’s a case to be made that the Cubs should be sellers at the deadline to help build the farm system and get the jump on what may have to be another rebuild soon.

That wouldn’t sit well with the fanbase, for sure. Yet it’s an interesting debate, one that the front office is working through now. Again, the guess is that they’ll take the safe route and make a small trade or two to help upgrade this year’s team. We have to think about the future as well and how much stock we want to put into 2020. We’ll all be watching to see what happens.