Jed Hoyer deserved his contract extension with the Cubs

Cubs fans have said it all about Jed Hoyer:

Risk averse. Theo's yes man. Small market GM. Ricketts' front man.

What about three-time World Series Champion? Successful baseball executive? Straight shooter, strong talent evaluator, leader?

When the 2025 Cubs started to rattle off wins in May, Jed's contract extension was inevitable. To the dismay of many fans, he will sit atop the totem pole at Wrigley Field for at least another few years. His tenure as President of Baseball Operations hasn't been perfect, but I believe he deserved his recent contract extension.

The Transition

When Theo Epstein announced he was stepping down and leaving the Cubs in November 2020, it was a shock to everybody. His contract lined up with his philosophy of staying in one place for a maximum of ten years, but he decided to leave a year early. To his credit, he was confident in the transition plan and had full trust in Jed Hoyer to take his job and succeed.

Everyone in Chicago loves Theo, but he jumped off a sinking ship before it went underwater.

The offense broke in 2018 and was never fixed. Ownership was declaring "biblical losses" from the COVID season, star players were trending down, and the farm system was depleted. Who wouldn't want to leave that situation?

And that's where Jed's tenure began. On the precipice of a giant cliff.

He started his new job with budget cutting demands from ownership, so he said goodbye to Kyle Schwarber for nothing and Yu Darvish for a handful of teenagers. Somehow, Tom Ricketts found some cash in his jacket, and the Cubs gave Joc Pederson $7M when Schwarber would have cost them $9M-$10M. Were they still trying to win??

This was the 2021 Opening Day lineup:

Pitchers who started 20+ games:

MAYBE they could get lucky and win a lot of slugfests on their way to a playoff spot...

Well, everything felt great when they were 42-33 on June 24th. Then, in Bears-like fashion, they lost 11 straight games and sent the direction of the franchise into a spiral.

I didn't think trading away the championship core was even on the table. All of a sudden, Anthony Rizzo was taking pictures in the ivy at Wrigley as he said his goodbyes.

Reshaping the Organization

Where do you start when an entire organization needs an overhaul?

If Theo and Jed's plan from 10 years prior was the blueprint, it meant trading away everyone worth a penny on the major league roster and acquiring as many quality prospects as possible.

When the core was traded away, it felt like we were back to the startling line. A 10 year cycle. The end of consistent contention. Another full-scale rebuild.

The Cubs needed to be fixed.

Instead of digging up the old schematics, Jed paved his own way. He has utilized nearly every avenue for improving the organization’s talent level.

Draft: Matt Shaw, Cade Horton

Developing homegrown players: Justin Steele, Miguel Amaya, Daniel Palencia

Re-signing homegrown players: Ian Happ, Nico Hoerner

Trades for minor leaguers: PCA, Michael Busch

Trades for major leaguers: Kyle Tucker

Free Agency: Seiya Suzuki, Dansby Swanson, Carson Kelly, Shota Imanaga, Matthew Boyd, Jameson Taillon

Ownership still gives its best effort to hinder his approach, but he has figured out how to operate with those constraints. Just this year, he was beat out financially for Tanner Scott, was granted a special exception to exceed the budget and flat-out underbid for Alex Bregman, was forced to salary dump Cody Bellinger, and didn’t utilize the extra money in the offseason or at the deadline. The Cubs’ baseball budget could be way higher.

Looking back at the last few years, Jed accelerated the rebuild by trying to compete and rebuild at the same time. The last two seasons ended in disappointing fashion with 83 wins each time, so he failed to achieve that goal. Trying to thread the needle probably hindered the type of losing and prospect acquisition that could lead to having a great core in the future.

Even though it didn’t work, all of his efforts to add to the team have culminated in an excellent mix of players in 2025. If he had waited around and focused solely on prospect acquisition, about half the diamond would be a big unknown. Maybe he could have pulled off trades for higher rated prospects who could become franchise cornerstones, similar to the 2011 plan, but it’s hard to say.

Trading away the core was the right call. Letting Willson Contreras walk was the right call. Adding Shota Imanaga and Matthew Boyd to the rotation were the right calls.

He targeted PCA. And Busch. And Tucker. And all of these players who are now playing at elite levels superior to most other players in the league at their positions.

The 2025 Cubs and Beyond

So here we stand after 4 and a half years.

Instead of being stuck on the downhill slope of the world’s largest mountain, the Cubs are climbing yet again.

I know a lot of people are down because of the Trade Deadline, and believe me, I wanted the Cubs to find an elite starting pitcher.

But where they are at now compared to 2021 is night and day.

They are 1 game back in the division and in the entire National League post-Trade Deadline.

Their farm system was rated as one of the best in the league before players like PCA graduated to the show, and now it remains in the Top 10-15 after more players like Matt Shaw made the jump this year.

Dansby Swanson is the only player with a guaranteed contract after 2026, so there will be financial flexibility.

Four position players are currently playing like superstars (Tucker, PCA, Busch, Seiya), recent free agent signings have been absolute steals (Boyd, Kelly), and the front office has been churning out successful draft picks who have mostly been used as trade capital. The Dan Kantrovitz hire has made a huge difference.

Despite the loud, dissenting fans, everyone with the Cubs loves Jed. The players appreciate his honesty and trust his ability to add to their team. Assistant GM Dansby calls Jed night and day and only came to Chicago because he was sold on Jed’s vision for winning championships. Craig Counsell left a great situation because he believed in Jed’s approach to building this organization.

If this is the 2025 to last decade’s 2015, winning a ring by now would never have been the expectation. It does mean we’re approaching another window of contention, and I’m excited about how well this team is set up.

The positive side of a quieter trade deadline is that all of their top prospects are sticking around. Now the Owen Caissies and Kevin Alcantaras of the world can start in the OF at Wrigley in a year or two, or it just means the blockbuster trades will be delayed a few months. Either way, the infrastructure is in place.

Jed talks about sustained success and avoiding peaks and valleys. I only hope he solves that challenge and corrects the biggest mistake from his tenure as GM. Finish the job with a championship. THEN continue to contend every single year.

Let’s give him a chance to take this to the finish line and beyond.