First Pitch: Who will the Chicago Cubs trade first, and why?

As Chicago Cubs fans embrace a battle between their inner nostalgia and an obvious rebuild, Jed Hoyer takes trade calls.

2016 wasn’t all that long ago. The Cubs were in the middle of an expected run, built by front office savant Theo Epstein in an effort to revive a once-great baseball franchise into far more than a lovable loser. Epstein succeeded at that, but just five years later the walls are crashing down. Unlike the infamous 2013 webcomic from K.C. Green, everything is not fine. In this meme, a franchise burns to the ground, as is the case with any and all ‘retooling’ or ‘rebuilding’ efforts. The verbiage is interchangeable, and not all that important.

Hoyer’s official rebuild started this summer, in letting Kyle Schwarber and Jon Lester walk to the Nationals, and trading ace Yu Darvish — fresh off finishing third in NL Cy Young voting — within the league to the San Diego Padres. Cubs fans have expected such moves for years now due to a lack of payroll flexibility from the Ricketts’ family. A shortened 2020 season, in which the majority of professional baseball teams were hemorrhaging cash, surely sped up the process.

With that, four once-glowing stars remain on the North Side. Kris Bryant, Willson Contreras, Javier Baez and Anthony Rizzo will all be in the Opening Day lineup at Wrigley Field on April 1 for the Cubs home opener, assuming a surprising transaction doesn’t happen first. Bryant and Contreras were shopped all offseason, but to no avail for Hoyer. Meanwhile, Baez and Rizzo enter free agency after the season barring contract extensions.

The official end to this Cubs run, at least as fans know it, could come as early as next Winter — if not sooner.

Should Chicago Cubs fans embrace the end of an era, or fight back?

Frankly, Cubs fans don’t get much of a say in the direction of the franchise at this point. Hoyer is under the direction of ownership, and he’ll attempt to make the best deal possible should it present itself. But for some of the best supporters in baseball, that doesn’t make it any easier.

For insight on the matter, I spoke to a Cubs fan — and an informed one at that — in Cubbies Crib site expert Jacob Misener.

1. PECOTA projected the Cubs to win around 85 games this year. Is that a justified expectation given the uncertainty around some of the team’s biggest stars?

I don’t think anyone can say with any degree of certainty what this team A) will do over the course of the season or B) look like post-trade deadline. It’s not just the question as to whether or not the core group will bounce back after all struggling in 2020. We don’t even know how many of them will make it past the trade deadline. Jed Hoyer is going to listen on anyone who doesn’t agree to an extension this spring with an eye on the future rather than risk watching them walk and getting nothing come the end of the season. -JM

2. Cubs fans understandably feel attached to the 2016 team. As the core of that squad is now being mentioned in trade rumors (at least a few of them), have fans come to terms with perhaps moving forward with the retooling Jed Hoyer and the front office is pushing on this franchise?

No. The Yu Darvish trade really rubbed folks the wrong way. I don’t think it was so much the re-tooling that upset fans, but the return — which was largely made up of high-risk, high-reward prospects. I think a lot of fans are really struggling with the fact this team never turned into the dynasty we all expected back in 2015 and 2016. As for me? Change is long overdue on the North Side and as much as I love that 2016 team, it’s time to move on. -JM

3. Out of this core four — Kris Bryant, Willson Contreras, Javier Baez, Anthony Rizzo — how many players would you expect to be on the team at this time next year?

Two. I think Chicago manages to extend Baez and Rizzo. I suspect Bryant has a strong first half and the Cubs trade him at the deadline and they continue their re-tooling next offseason by trading Contreras for a package centered around high-end pitching prospects. They keep Baez for what he’s capable of doing on the diamond — and he stays to avoid battling next winter’s loaded free agent class of shortstops. Rizzo? He’s the closest thing to Mr. Cub we’ve seen since Ernie Banks himself. -JM

4. Javier Baez, for one, has been linked to a contract extension to stay in Chicago. Is that the right move for the Cubs future?

Yes. I don’t think an extension with Baez will be anything earth-shattering, really. I’m guessing it’s somewhere in the five-year, $100 million range (or at least around that low-$20 million AAV mark). If I represent Baez, I’m not so sure I want to be in that aforementioned free agent class that’s dripping with top-tier shortstop talent, especially coming off the worst season of his career. If he doesn’t agree to an extension this spring, everything rests on his bouncing back — and that’s a big risk. -JM

Whether the Cubs window is closing on its own, or if Hoyer and ownership are forcing it closed due to financial constraints, remains up for interpretation. One way or another, the team should look much different a year from now.

First Pitch is a weekly FanSided.com MLB feature in coordination with the FanSided network.