Off the top of my head, I believe the Cubs signed Jon Lester to a $150 deal in December of 2014, coming off a 71-91 season. I bet I can find more examples if I spend 5 minutes looking them up. Perhaps they felt they already had the pieces needed to compete, and were simply adding to it. Sort of like the Twins, with Sano, Buxton, Berrios, Kepler, Rosario, Polanco, etc. The exact guys they've been building this "window" around for half a decade. I just have never agreed with the philosophy of waiting until you're really good, before you try to get really really good. IMO, that's how you spend decades waiting to get really good. Tha's not how the Yankees and Red Sox got where they are. They assess their needs, and then fill them, by whatever means necessary. Or at least try.