Better Roster, Cubs or Sox Where Will Castellanos Land

I have been seeing a lot of this intriguing talk on which Chicago team has the better roster. Just eight months ago this wouldn’t even be a conversation. The answer was hands down, the Chicago Cubs. They were firmly within their window to compete. The Chicago White Sox, on the other hand, was coming off a 100 loss season after a 95 loss season. They hadn’t sniffed the playoffs in 132 months or 4,015 days. The Cubs had spent the last four seasons in the playoffs, and in three of the seasons making deep playoff runs which resulted in a World Series win.

But after a very disappointing 2019 season on the Northside, and the firing of the beloved Joe Maddon, faith in the Cubs roster has dwindled. The other side of town has seen a ton of excitement with regard to their young talent. Lucas Giolito was an ace. Eloy Jimenez showed the White Sox a glimpse of his greatness. Players like Tim Anderson won people over with his eccentric play and they are just warming the oven for Luis Robert, Nick Madrigal, and Michael Kopech.

The Cubs, on the other hand, are discussing which player they should trade. They missed the playoffs after losing in the Wild Card game in 2018, and the window is still drafty but potentially shutting.

These reasons are why guys like Ken Rosenthal and Jon Heyman can openly say that they would prefer the White Sox roster over the next five years.

Would you rather have the White Sox or Cubs roster the next five years? #MLBNow pic.twitter.com/WFOIcDGRic

— MLB Network (@MLBNetwork) December 1, 2019

Heyman and Rosenthal really latch onto the length that the Cubs have their stars locked up for as opposed to how long the White Sox have their prospects locked up for. I say prospects as, outside this past season, the White Sox kids haven’t done anything. Do you recall Kyle Schwarber’s splash onto the baseball world? How about Addison Russell or Ian Happ or Albert Almora?

What I’m saying is, not all prospects pan out. You might have a strong feeling about a player or two here and there, but until that player has been seen by MLB pitching for more than a season you just don’t know what you have. Schwarber looked like he was going to hit 50 homers a season, bat around .280 or higher, get on at a .375 pace or higher, and slug at a ridiculous rate. But after five years as a pro, Schwarber had his best season ever while slashing .250/.339/.531 with 38 homers and a 120 wRC+.

The next point that they make is, with how deep the White Sox are, talent-wise, there is much more flexibility in being able to make trades or fill holes internally. While yes, the White Sox have an incredibly deep farm system right now, the Cubs also have the ability to trade some of their current MLB veterans to either help rebuild their farm – all the while staying competitive at the big league level. In fact, that is what Theo Epstein and Jed Hoyer are trying to accomplish this offseason.

I don’t believe the White Sox will win a World Series in the next two seasons, and while I have reservations about the Cubs, I think they’re more likely to do so that the Sox are. If the Cubs win another World Series in the next two seasons and the White Sox fail to win one in the next five, wouldn’t it be better to be the Cubs over the next five years?

Where will Nick Castellanos land?

There is word that the Cubs are still very much interested in bringing Nick Castellanos back to Wrigley Field. The only issue with that is, the other teams lurking.

The White Sox have also kicked the tires on Castellanos, Jon Morosi suggests that the San Francisco Giants are also in on the free-agent slugger. This makes a lot of sense since new Giants general manager, Scott Harris, was the Cubs assistant general manager. He played some part in bringing Castellanos to Chicago and very well could play a pivotal role in bringing him to San Francisco.

Giants president of baseball operations, Farhan Zaidi plans on pursuing power and hitting this offseason. Castellanos can fit both molds.

He belted 27 homers in 2019, 23 in 2018, and 26 in 2017. He has much more power than what his outputs have shown, which was mostly been subdued due to Comerica Park. Coincidently, jumping over to San Francisco’s Oracle Park might be harsher on Castellanos.

According to the 2019 Park Factors, Oracle performed as the worst offensive park in baseball. It was equally bad with regard to homers and doubles – both things Castellanos brings to the table. So while dollars will always make sense, Castellanos wouldn’t move to San Francisco to become an offensive leader in baseball. On top of it, Oracle is one of the toughest outfield’s to play, which could magnify Castellanos’ deficiencies in the field.

With Castellanos projected to earn a modest four year deal for $56 million, I don’t know why the Cubs wouldn’t keep track of his negotiations. This projection is also at a range which should attract many other suitors. Just about anyone looking for an outfielder or even a DH shouldn’t pass on a call to Castellanos or Scott Boras.

While the projections are at four years and $14 million a year, I see team bidding this up quite a bit. Not certain he will fetch a $20 million AAV, but I can see a team winning a bid with additional years.