As far as long term planning, the Cubs have not been remotely smart for probably 6-7 years. I think we sparred on this in the past and I'll agree that they may have chosen the wrong targets, but I do think there is a very specific time to overpay players and it is when you have a 3-4 year window of controllable, cheap players. The Yankees seem to be OK almost always paying the luxury tax and sneaking under for a year or two. The other bigger markets are OK with it for 2-3 years. So maybe the Cubs chose wrong on some (Heyward, maybe) but the one time I am OK overspending is if you have a Rizzo, Bryant, Baez, Contreras to build around for a small $ amount. Then you can overpay and know you're going to dip into luxury tax with Lester, Heyward, Darvish, etc. In the end, the Cubs' demise was not having enough pitching come together at the right time. Hendricks was a great home-grown pitcher but that is honestly about it. Kimbrel was an overpay that somehow didn't pay off for 2 years. This is also why I laughed at the Arenado move for the Cards. They already had an aging roster where they've dealt away minors depth. They're not a team that's going to go into the luxury tax often. So they dealt for Arenado to be an 80-85 win team and not much room to grow. Then they'll deal with 4 years of crap Arenado contract on the back end. Bad timing. For the Cubs the timing was right, the players were not the best. That's fair to a degree. One thing I'll add, the Dodgers have been in a competitive window for a long time as well...yet they've made a point not to trade away guys they recognized would be elite talents. Bellinger, Lux, Smith, May, Urias, etc. The Dodgers surely recognized these players would actually be good, while also recognizing that Diaz was overhyped. Verdugo goes against that theory, but they were getting Betts so it's a bit easier to make peace with trading someone who's actually going to be good. The Cubs didn't do this with Jimenez/Cease/Torres/etc. The Dodgers admittedly are just way better at developing players than pretty much anyone else so they have more prospects to consider, but they didn't just go sell the farm for rentals every time they had a good record. The Cubs are a top 5 market and there's just no reason they couldn't operate like the Dodgers and have a 10+ year window of being reeeeeally good. Instead they traded away every top prospect they had for rentals and narrowed their window to 4-5 years. Frankly, the other top 5-10 markets should be looking at how the Dodgers operated over the last 5 years and try to copy it. They've had 90+ wins every year since 2013 aside from last year(43-17) along with 1 world series(really should be 2) and should be a 90+ win team probably for the next 4-5 years with the talent on the roster.