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

The downfall of the Chicago Cubs World Series winning core in 2016 was the fact that the team was unable to secure contract extensions with any of the star players from that team. Javier Baez was the closest member of the 2016 core to signing an extension as the team was believed to be in the final stages of a new deal in 2020 prior to operations shutting down due to the pandemic.

Baez was traded to the New York Mets at the Major League Baseball trade deadline in 2021 and that was the same deadline at which the Cubs moved first baseman Anthony Rizzo and third baseman Kris Bryant. The decisions that were made at the trade deadline led to a rebuild for the next season and a half and, to the Cubs' credit, the decision was the right move.

While the hardest part of the rebuild has yet to arrive, that part being the prospects reaching the Major League level and then finding success, there is no question that the team has established a pipeline of quality prospects that are expected to reach the Major League level over the next few seasons.

The arrival of prospects such as Pete Crow-Armstrong, Brennen Davis, Kevin Alcantara, and Hayden Wesneski will coincide with the Cubs' intention to return to contention at the Major League level. As the Cubs open their contention window back open again, there is one extension that the team should make soon and another extension that the team should avoid.

1 extension the Chicago Cubs should avoid: Left fielder Ian Happ

Ever since the midway point of the 2021 season, Ian Happ has done everything right in terms of his development at the Major League level. The work that Happ put in resulted in a breakout season in 2022 as for the first time in his career, he was named to the National League All-Star team while also earning the first Gold Glove award of his career. Happ was a 3.5-fWAR player last season while posting a 120-wRC+. If Happ has a repeat performance in 2023, there is no question that he will place himself at the top of the free-agent list next offseason for position players and that is why the Cubs should avoid signing him to an extension.

Wait...what?

The Cubs need to show an inclination toward signing their homegrown players, yes. The Cubs need to show an inclination toward signing top free agents, yes. Therefore, the Cubs should do whatever it takes to sign Happ to a contract extension? No. Most of the Top 100 prospect lists that have been generated from various outlets over the recent weeks have three Cubs' prospects listed. Those prospects are outfielders Pete Crow-Armstrong, Brennen Davis, and Kevin Alcantara. Not mentioned are fellow Cubs' prospects, also outfielders, Alexander Canario and Owen Caissie. If the Cubs are confident that, at the very least, two of those five outfield prospects will be better than Happ, then the team will need to move on from their current left fielder and avoid an extension.