This is a ‘can’t-miss’ trade deadline for the Cubs front office

Over the better part of the last two years, the Chicago Cubs have made an incredible amount of trades, roster moves and free agent signings. Though fans have ultimately been disappointed with the team’s “lack of spending” this past winter, seemingly showing an acceptance when it comes to  putting a poor product on the field, it is important to remember there are several moving parts when it comes to a rebuild.

For one, fans must remember that Jed Hoyer and Carter Hawkins can only spend money once green lit by the owner himself, Tom Ricketts. Ultimately, it is the owner that provides the funds for these major signings. Yes, it is frustrating to see the Cubs have over $100M available in payroll and not use it when they could put a competitive product on the field this year if they wanted to. However, we must be reminded of how the rebuild process works and why the Cubs didn’t go all-in this year.

After trading Kris Bryant, Anthony Rizzo, Javier Baez and Craig Kimbrel, along with Yu Darvish before the start of last season, the return the Cubs netted at first seemed underwhelming. Fast forward one year: three of those guys are now among the organization’s top 10 prospects and are rapidly ascending industry lists, as well. As it turned out, it appears that Hoyer and crew have a keen eye for acquiring talent via trade after all.

However, that was then and this is now. I firmly believe the reason the Cubs haven’t emptied their pockets on free agents yet is simply due to the fact that they want to get the most out of who they do sign to a big contract. Freddie Freeman for example, elite as he is, was 32 when he signed a six-year deal with the Los Angeles Dodgers this past winter. Nick Castellanos was already 30 years old when he signed up to play ball with the Philadelphia Phillies. These guys were looking for a huge multi-year pay day, knowing it would be the most lucrative deal they could sign in their career.

For the Cubs, they didn’t want to sign six-year deals with guys who would be starting to decline three years from now and potentially take a risk on them underperforming when the next core is ready to go. Instead, it seems likely they will wait to spend on these All-Star-caliber players when the time is right to keep their next competitive window open as long as possible. Essentially, this scenario is frustrating for the Wrigleyville faithful, but will all be worth the wait when the Cubs clinch their next playoff berth.

If all goes well regarding the farm system’s development, truth be told, that is the best chance the Cubs will have for long-term success as opposed to tying up a bunch of money in guys that may only produce for the next few seasons and then be stuck with them on the books for another three years after. I understand the vision personally and implore any doubtful Cubs fans to look at the situation in this light.

In regards to this year’s trade deadline and potentially adding more strength to an already revitalized farm system, the chance for the front office to really shine is right now. Over the past season, the front office has been critiqued and blamed for the downfall of the Cubs organization. Can you really blame Hoyer or new GM Carter Hawkins? For one, Seiya Suzuki has been a smash in his first year in the MLB and Marcus Stroman’s struggles could not have been foreseen based the the seasons he has had of late.

Chicago Cubs: The front office must shine at the trade deadline

Now, however, it is time for phase two of this rebuilding process. The goal simply this season, if you aren’t going to re-sign Willson Contreras and Ian Happ, go out and package as many deals as you can around then to acquire at least 1-2 top 100 prospects that are somewhat near MLB readiness. The Cubs farm already has gone from one top prospect to four in the top 100 this year alone.

If Chicago secures another top prospect or two ahead of next week’s trade deadline, I personally  believe Hoyer will be in the clear and should be given the benefit of the doubt regarding how he is handling things. Trading Contreras and David Robertson seems inevitable at this point. Happ, however, I can just as easily make the argument that he should now be extended instead of traded as he is having a career season, notching his first All-Star selection at just 27 years of age.

For perspective, Suzuki, who is also 27, was brought in to be part of the next core. I see no reason why Happ, at the same age with a mightily improved game on both offense and defense, can’t be part of that as well. If they do trade him, they need to find a way to package him and get another top 100 prospect in return.

All told, if they wind up keeping Happ, I’m all for it. If they trade him as part of a package and net a high-quality prospect, I’m understanding and can’t exactly complain, since it will give the Cubs another core piece with more team-controlled years at a younger age. What I can’t accept is trading him by himself for a couple guys that are years a way and are a coin flip if they’ll work out at all.

Either way, the front office must shine here. Netting two top 100s, or keeping Happ and getting a top 100 for Contreras/Robertson dramatically improves the team’s chances to compete again soon. Then, the high dollar contracts will come.