5 Chicago Cubs players facing uncertain futures after 2023

5 uncertain futures - 1. Ian Happ

Last and certainly not least, we land on Cubs All-Star Ian Happ. After a stellar showing in 2022, Happ's uncertainty is due to whether or not the front office continues its trend of not extending key players. Granted, there have been reasons in the past with former core members that made the argument of not over-paying guys feasible points. Players that have been underperforming when talks went sour, catchers that weren't the best defensively, etc. On the other hand, Happ has begun checking all the boxes of a player who you have to dig deep to find weaknesses. And that is the biggest problem.

Given what we saw with the free agent market this winter, the money spent on players is at an all-time high. When you center your whole life around becoming a baseball player, one of your biggest dreams is to reach free agency and secure that monster payday. That is where Happ is currently in his career, and with another good year overall, his price will be high enough that he may want to test free agency no matter what to see what's there. Unfortunately, It's hard to hold that against him. For the Cubs to extend him and avoid free agency, they may need to get creative.

Contract-wise, a solid AAV with built-in incentives on top of it may do the trick. A bonus for the top 10 or 15 for MVP, rewards for specific statistics or accolades, All-Star earnings, Gold Gloves, etc. That way, regardless of what he does throughout the season, he will not find himself getting underpaid or overpaid. Of course, he could always bet on himself, avoid such incentives on a contract, and go for a higher AAV regardless of production. If he wants to be a Cub long-term, this may be the easiest way to ink a deal before the 2023 campaign concludes.