The Curious Case of Crane Kenney

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One of the people in the Chicago Cubs organization that might be the most maddening to their fans might be the Cubs President of Business Operations Crane Kenney. By simply mentioning his name, you can generate more emotion from fans than almost anything else connected to the Cubs, as he is responsible for just about everything the Cubs organization has done from a business standpoint.

From a positive view point, Kenney is solely responsible to helping the Cubs get their brand new, state of the art Spring Training facility, which might actually be the best Spring complex in all baseball, and might even rival some facilities at the Major League level. At very least the new Spring complex in Mesa is miles ahead of what the Cubs Major League ballpark currently have. I love Wrigley Field, but the place needs some serious work to get modernized just in terms of the clubhouses.

With the new complex in Mesa, the Cubs players will have a simply amazing place to prepare for the upcoming season, and put them at least on level ground with the other top teams around the league. They will want for nothing in that Spring home, and will feel very comfortable there for years to come.

Kenney has also done great things for the Cubs by assisting in the building and planning of the Cubs new, state of the art Academy which will help them find the best Cuban talent. With this academy under the control of the organization they will be there 24/7 scouting and researching every player in the vicinity. If there is another Yoenis Cespedes or Yasiel Puig out there, the Cubs will be the very first organization to find them, which means they will likely be the first team that has a crack to get them under club control. By doing so, they have the opportunity to keep these players from hitting free agency and going to another organization because the Cubs were outbid by other teams.

Kenney has done great things for the Cubs organization; and if those were the only contributions he made with the organization, then I could see no reason to hate him at all. In fact, these are only two instances that come to mind with why I feel he should not be thrown under the bus completely. He has done many positives things for the organization in his long tenure here.

However, while there are positives things you can look at and say he has done a lot to help the Cubs get a clear advantage in some areas, he is also responsible for some of the issues that are holding the organization back.

Most recently would be the Masahiro Tanaka derby. He put massive pressure on the organization to sign him when he came out and stated that the Cubs would not be outbid in negotiations for his services. That’s right, Theo Epstein and Jed Hoyer were not the ones who said anything about the Cubs outbidding all competition for Tanaka’s services. He took the matter upon himself to put the Cubs on center stage, believing he was doing them a service, when in fact he was putting them squarely behind the eight ball and in a do or die situation. Once he said that, and the word circulated about his belief, no one in the Cubs organization could really deny that statement without some major public relations backlash.

If you had not have heard that the Cubs “would not be outbid” how upset would you be that the Cubs were in fact outbid? As a matter of fact, while they were outbid, is $2 Million a year really all that much when you are already making $20 Million? Not likely. What did them in was the opt out after four years and the full no trade clause, both of which the Cubs did not want to include in any deal.

However, one of the biggest mistakes Kenney might have made, was being the mastermind behind the contract with the rooftop organization which is holding up all of the renovation plans. When he was employed with the Tribune Company, he held the position of President of Business Operations, the same position he currently holds under the Tom Ricketts regime.

According to a tweet from Dave Kaplan, the contract with the Rooftops is very friendly, for the Rooftops.


That might be the most damaging thing that he has ever done while employed for them, and might cost Ricketts millions of dollars if they want to buy out the remaining years of the contract. Business men like Ricketts do not like losing money, and Kenney’s blunder in writing a contract that favored the rooftop over his employer (Trib Co & the Cubs) is pretty boneheaded.

I am sure that he thought he was doing something good, getting millions a year for his boss from small business leaches who were steal from the Cubs for two decades before the contract was offered. The Cubs however, held all the leverage and Kenney could have done anything in that contract and the rooftops would have had to agree to any and all conditions if they wanted to continue selling tickets to view the Cubs product, but Kenney did not do that. He practically gave the rooftops complete control over their sight lines which is preventing the Cubs from the proposed renovations that will help generate millions of dollars on advertisements alone.

If you are interested, our friends at Obstructed View have a great piece up on why they do not support the rooftops.

In his defense, ten years ago I am sure no one ever envisioned the Cubs wanting to add a large video scoreboard or throw up advertisements around the ballpark, but that is not really an excuse to write up a contract that benefited thieves of your product when you held all the cards. Without the contract, the Cubs could have sued the rooftops for everything they owned and shut them down, but Kenney wanted to make as much money as he could for his employer, the future be damned.

I am not sure if all the good Kenney has done to put this team leaps and bounds ahead of several teams in terms of scouting and development is nearly enough to outweigh the bad he has done with the mess he got the Cubs into with the rooftops. That deal is standing in the way of the Cubs finishing their plans to make the team competitive in terms of generating enough revenue to be able to afford those big name free agents everyone craves.

One thing I know though, if RIcketts has to pay millions of dollars to the rooftops to make this problem go away, that might cost Kenney his job.

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