I'm not a Cubs fan, I'm a White Sox fan, so I don't care one way or the other, but he's WAY overrated for the money he's looking for. I live in Houston and I've seen his entire career, and what he is is an outstanding second or third bat in a great lineup. It's a lot easier to put up those big numbers he's had when he's been in a lineup with Jose Altuve, Jeremy Pena, Alex Bregman, and hitting directly in front of Yordan Alvarez who when healthy frightens pitching staffs, leaving Kyle with plenty of good pitches to feast on. But it's a lot harder to put up those numbers when all the lights are on you. When you're expected to be The Guy, the bell cow, the lead dog, the centerpiece of the lineup.
If he can be had for $375-400 million, he'd be great to keep. But If he's insisting on $500 million or more, the Cubs would be a lot better off letting him, go and using that money on getting a couple of top-of-the line starters, or getting a stud starter and a reliable closer. With Justin Steele coming back plus a major upgrade to your pitching staff, the Cubs can be truly lethal next year. Just my opinion as a non Cubs-hating Sox fan.