1 extension the Chicago Cubs should make soon and 1 they should avoid

Contract extensions haven't exactly been the priority for the Chicago Cubs during both the Theo Epstein and Jed Hoyer regime but as the team enters a 2025 season where the expectation is to reach the postseason, it's a practice that Hoyer may want to utilize.

Prior to the 2023 season, Hoyer inked left fielder Ian Happ and second baseman Nico Hoerner to three-year contract extensions. By identifying two pieces of the Cubs' core at the time, Hoyer was providing the team with cost certainty in the seasons ahead.

Ironically, Hoerner could be traded as soon as next week at the MLB Winter Meetings.

That same cost certainty Hoyer was seeking with the Happ and Hoerner extensions is something that he will need to look for as the team's top prospects begin to reach the Major League level. Pete Crow-Armstrong has already reached the Major League level with Matt Shaw and Owen Caissie not far behind him.

If the Cubs are going to continue to avoid the deep waters of free agency, the team will need to keep a close eye on the success their prospects are having in the early days of their Major League careers and determine if it would be wise to sign them to an extension now rather than wait.

Cubs' contract extension needed - Pete Crow-Armstrong

One of the truest signs of a healthy organization is identifying the players who will be a part of their core and wasting no time in extending them. The Milwaukee Brewers' contract extension with Jackson Chourio last offseason is proof of that.

Pete Crow-Armstrong has reached the status that Chourio has with the Brewers following the 2024 season but the Cubs should be encouraged by how Crow-Armstrong finished during the closing months of the season. If Crow-Armstrong builds upon that success at the start of the 2025 season, the Cubs would be wise to open contract talks.

Cubs' contract extension avoided - Justin Steele

Justin Steele has always been in the background regarding players on the Cubs' roster who should get a contract extension. Even now, turning 30 next July and not a free agent until 2028, the argument could be made that he is a strong extension candidate as a way for the Cubs to buy out his remaining arbitration seasons.

Steele remains at the top of the Cubs' starting rotation but it is worth noting that he has had alarming forearm injuries in each of the past two seasons. That is an ominous sign for what may arrive in the future. Given that sign, along with the health of the Cubs' pitching infrastructure and prospects, it seems that the team will be comfortable with letting the arbitration seasons play out for Steele.