Cubs insider floats an important lesson front office should have learned

The Chicago Cubs going out of their way and choosing to avoid the top-end of the market in terms of free agent targets each offseason has all but confirmed that the team's contention window will be carried by the organization's top prospects.

Sure, the Cubs have shortstop Dansby Swanson in the middle of a seven-year contract and traded for one season of Kyle Tucker but if the team is going to have sustainable success, it will be on the backs of the prospects at the top of their farm system rankings.

The two prospects at the center of that expectation are third baseman Matt Shaw and center fielder Pete Crow-Armstrong. Admittedly, we are using the "prospect" term loosely with Crow-Armstrong considering he spent a healthy amount of the 2024 season as the team's starting center fielder.

With Shaw and Crow-Armstrong penciled in as everyday starters in the Cubs' starting lineup, we've reached the point once again where we are hoping the front office has learned from their past mistakes.

One of the biggest missteps the front office under Theo Epstein was they did not try to extend the core in the early seasons of their MLB service time. Sure, in hindsight, that appears to have been the right move but that isn't the trend of Major League Baseball. If the Cubs want to have sustained success like the Atlanta Braves, or more to their liking, the Cleveland Guardians and Tampa Bay Rays, they need to be willing to broach the idea of contract extensions with the young players of their core.

That would be the reason Sahadev Sharma floated out the idea of an early extension for Crow-Armstrong. Sharma's premise for the early extension is that if Crow-Armstrong's strong second half of 2024 is an indicator of what is ahead, the Cubs would be wise to create cost certainty and buy out his arbitration seasons in addition to tacking on some years of control.

If not top free agents, Chicago Cubs should be willing to pay their top prospects

It's not a model that a team like the Chicago Cubs should depend on but in a world where Tom Ricketts implements restraints on spending, no matter the offseason, the Cubs will need to ensure they lock up their young prospects, assuming they believe in the talent, as early as possible. It's the only way that the team will achieve a streamline of success.