2. Kyle Hendricks: 2024 salary of $16.5 million
At 34 years old, Kyle Hendricks proved he still had enough gas in the tank to warrant not only a rotation spot but also a club option for 2024 worth $16.5 million. That's probably a little much for Hendricks' services, but given the guy won an ERA title, clinched a pennant, and helped win the 2016 World Series, it'd be hard to send him packing without leaving a sour taste in everyone's mouth.
As for next offseason, we will have to see how much Hendricks wants to be a Cub when he hits free agency. We've seen time and time again that money talks in this league and I don't see the Cubs offering Hendricks a player-friendly deal with the kind of pitching infrastructure the organization now boasts. It's nearly impossible to project what Hendricks will make when he hits free agency next winter, but I can comfortably say that he won't be getting $16.5 million a year from the Cubs unless he wins the Cy Young award.
Now that doesn't mean I don't want the Cubs to pay him that, I just think it's unlikely from a realistic standpoint. I'd love nothing more than for Hendricks to be a career-long Cub because of the memories he gave us over the years. But the same could have been said for Willson Contreras, Kris Bryant, and Javier Baez at one point in time. Baseball is a business at the end of the day.