The Chicago Cubs are the 4th most valuable team in MLB but can't be bothered to spend

We know that Chicago Cubs president of baseball operations Jed Hoyer likes to spend “intelligently.” He won’t go beyond what he feels comfortable with in a league full of teams that will, which has led to a string of mediocre seasons. 

History of Player Retention

The funny thing is that the unwillingness to spend like a large market team hasn’t been Hoyer-specific, Theo Epstein was pretty similar. The problem isn’t necessarily with free agent spending, the problem is with retaining the home-grown talent that the Cubs have cultivated through decades upon decades of rebuilds.

If you were to look for the largest extension in franchise history you’d have to go all the way back to 2007 when the Cubs signed Carlos Zambrano to a five-year $91.5 million dollar extension, however even at the time Zambrano had this to say about his team-friendly deal:

"Not everything is about money, you know, I know if I got to free agency there were a lot of things that would come to me and offer me. I feel comfortable here. I feel good here and my family feels good here."

Carlos Zambrano, via ESPN

Since 2011, they’ve had 31 different players in MLB Pipeline’s top 100 prospects list, they’ve had players win Gold Gloves, they’ve had players win Rookie of the Year and they’ve had players win MVPs.

Of those players listed above the Cubs have extended… two of them. Last year Ian Happ and Nico Hoerner both received three-year contract extensions.

According to Spotrac, going into the 2024 MLB season there are 114 players that will be playing under a contract extension they received from the team they were previously under contract with.

Of those, 66 of those contracts were signed for five years or more. The Cubs have just one of those players and I can just about guarantee it’s not who you think.

It’s David Bote. 

Bote was lucky enough to be caught up in all of that intelligent spending as he inked a five-year $15 million dollar extension back in 2020 and has been in AAA pretty much ever since. 

When the Cubs had a core of Anthony Rizzo, Javier Baez, Kris Bryant, and Kyle Schwarber they traded three of them and non-tendered the other rather than give them an extension and instead focused on Kyle Hendricks who signed a four-year $55 million dollar deal. 

23 teams in Major League Baseball have a player this season playing under a contract extension of six or more years. The Cubs are not one of them.

The Atlanta Braves have seven players that they extended to five years or longer including Austin Riley, Matt Olson, Ronald Acuna Jr., Sean Murphy, Michael Harris II, Ozzie Albies, and Spencer Strider. Good thing we haven't leveraged our future like they have... They could definitely be in trouble soon with that young core under team control for the foreseeable future.