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