Crazy Offseason Plan #1: Chicago Cubs Edition

This is just a short thing while I’m in between larger projects, but I felt it was worth sharing. We’re finally in the offseason, and it’s time for backseat GM-ing. This is the result of a pair of stories, so let me introduce each of them first before explaining where they tie in.


The other day, you may have heard that the Phillies were shopping Ryan Howard. Many found this funny, in the sense that it’s debatable if any team would even sign Ryan Howard were he a free agent. I personally think he’d get a minor league deal at best. With that in mind, I don’t know that the Phillies would get any sort of return for Howard.

Meanwhile, the Cubs continue to look for pitching. The Cubs have one of the strongest crops of prospects (both in the minors and with cups of coffee last year) in the minors today; however, they’re all position prospects. The team has made no secret that they’re looking for an established pitcher. Obviously, they’re looking at the top pitchers (and I’d bet the aggressively pursue Jon Lester, or possibly Max Scherzer, although I feel like they'll stay away from James Shields), but you can never have too much pitching.

Which is where I see some overlap for these teams. Obviously, Ryan Howard isn’t a pitcher. But, the Phillies’ best trade chip right now is: Cole Hamels, signed at $90 million over the next four seasons (plus an option year) and more or less worth it. .

The Cubs might have the prospects to swing a deal for Hamels as is. But I also wonder if they couldn’t hold on to their Kris Bryants and their Jorge Solers by agreeing to also take on part of Howard’s salary. They obviously don’t need Howard as anything more than a bench bat, and could cut him as needed. But they also don’t have a lot of money locked up for the near future; how much money would you throw away per year to pick up Cole Hamels without giving up your best prospects?

There’s a lot of money there to play around with; Howard will make $60 million in the next two years. Maybe if you eat, say a quarter to a third of that, you get to keep Addison Russell, Javier Baez, et al. That could be worth it.

It’s also worth noting that this team is still operating well below their 2010 peak of $144 million. The Cubs are still a big market team, and not only that, but they have a lot of players locked in for cheap in the coming years, like Anthony Rizzo and Jorge Soler. It may be worth eating some of Howard’s contract in the interest of keeping that offensive core together while carrying a pitching staff led by Hamels, Lester/Scherzer, and Jake Arrieta.

(And sure enough, since I started writing this, this article has gone up, so I might be on the right track. I also forgot that they had put a waiver claim in on Hamels during the season.)

Either way, after the big start of luring away Joe Maddon, I’m betting on big things happening with the Cubs this offseason.