Reading the Fangraphs top prospects list reaffirms to me this should happen. Conventional wisdom for the best time to sign a mega deal is when you've got a critical mass of prospects either about to or having just broken into MLB. The Cubs did both last go around, bookending 2015 with Lester and Heyward. Even though Fangraphs paints a pretty rosey picture of the Cubs' minor league system, there's not a near term wave of prospects coming. The cohort of guys opening next year at Low A South Bend looks really impactful, but it's still a half dozen teenagers 3-4 years from the majors. There's still plenty of talent ahead of those guys in the pipeline, but it's not gonna be the deluge like late 2014/early 2015. But financially, that might actually make taking the leap more palatable? One of the problems with the last core was that the homegrown guys were all on the exact same timeline, which meant they were getting expensive all at once. On top of that, Lester and Heyward's contracts were similarly timed, so as they got older and worse, the homegrown guys got older and more expensive (and aside from Javy, worse). Because of that, after the spending spree in 2018, the team was pretty locked into a corner contract wise. And with a miserly owner refusing to lift his self imposed payroll cap, we saw what happened. A mega deal now would hit differently. Like I laid out above, the team's contractual outlook would still be pretty clean for the next 3-4 years. After that depends on a lot of unknowns, but if a few of those teens on the farm are the goods you've got an infusion of high end talent hitting the MLB club on the cheap right as Correa's deal is moving into its back half. That's a great way to blunt even the most albatross-y of contracts. If next year's FA class were better I'd probably say to hold off and focus on short term deals the rest of this winter, but I feel like Jed ought to take this shot in the next year or so. And with Correa's market being fairly small this is probably the best opportunity to nab a high impact guy.