For everything written about the Cubs since Ricketts took over ownership, they took a risk when they purchased the Cubs and its rickety old ball park (no pun intended). With each major roll of the dice, there is a decision, an outcome, an effect.
The first decision that Ricketts made was to take the highly leveraged structured deal proposed by Sam Zell. This high debt ratio has caused the team to divert millions annually for debt service. It has also limited any additional borrowing for capital improvements. It has also placed the team on the MLB watch list because the debt exceeds league standards (and MLB is afraid of teams going bankrupt and ownership being changed by the fiat of a bankruptcy court judge.) The deal has created a very weak financial team.
The second decision that the Ricketts made was the caveat that the family would not put any more investment money into the team. That meant that the Cubs had to sink or swim on its own revenues. This is also tied to the deal because the Tribune is a 5% partner, who would not contribute any more capital to the venture. As such, the Ricketts acquired the team with a very high payroll and very high debt service. After the first year, attendance has started to rapidly decline. With no infusion of new cash into the team, the team has to cut expenses and player payroll is the biggest slice of that pie.
The third decision that Ricketts made initially was to keep the Tribune's management team in place. In essence, new ownership kept old ownership executives who pumped up the deal in place instead of hiring their own independent baseball talent. In some respects, that has caused problems because the operating structure of the team was split field operations and business operations (dominated by Trib executives). One would assume that those Trib executives would hold fast to their prior view that the Ricketts got a good deal for the club, despite the set backs and onerous contract details.
The fourth decision that Ricketts made was hiring Theo Epstein to take over baseball operations. The Boston Whiz Kid was the hot commodity when he was booted from Bean Town. As a result, the baseball operations swelled with new hires, creating a two tier system of Tribune management and scouts and Theo's new crew. Epstein was not used to a financial restraint in Boston, where he could write big checks to gloss over bad free agent moves or obtain high price talent to fill gaps in the roster. With the Cubs, he was handcuffed by the financial deals in place. As a result, a new plan was adopted which was called the rebuilding program.
The fifth decision that the Cubs made was to tank seasons. By trading off veteran talent for prospects, it reduced the payroll of the team. By reducing payroll of the team, the Cubs could balance off falling revenues. By not signing free agents, the Cubs avoided the long term deals that lead to dead money payroll landmines. By filling a roster with journeymen players, the Cubs have sunk to the bottom. From their, the front office has used high draft picks to select "quality prospects." The whole rebuilding process is developing their prospects.
The sixth decision flows from the last one. The Cubs have put all their chips on their prospects becoming impact major league players, under six years of team friendly payroll control. The front office says trust us, we know what we are doing, but statistically, the odds are greatly against them. Only 6% of prospects become major leaguers. The various reasons for failure are injury, unable to keep up with competition, being blocked from promotion by better players, to family and personal matters. At this point, the Epstein-Hoyer team has not promoted one of their developed draft choices to the majors. The big roll of the dice is whether the team can field a roster of home grown talent that is competitive in the NL. Other teams, like the Royals, have tried for decades without much success.
The seventh decision is a confrontational one. The old Tribune guard was used to flexing the Tribune's muscle in the city. Politicians used to fear a major metro newspaper's power to control public opinion and election endorsements. But quickly, the newspaper and media properties have lost their clout as their readership and viewership have declined with the rise of the Internet. The Cubs grossly misunderstood their position when they first asked for public funds to rehab Wrigley Field. Then, they doubled down on trying to push through a massive real estate development project under the guise of "saving" historic Wrigley Field. The team has continued to alienate the neighborhood. The Ricketts want to have more events at Wrigley; they want to transform the intersection into a year-round party zone of their own new restaurants and taverns. Party at Cubs park is a major theme the business side of the organization is pounding on a daily basis in the minds of the public. Competition is one thing; but acting like a bully to muscle concessions from the city that the average businessman could not get is a risky proposal because the ire of the voters could lead to changes in ward.
The eighth decision was rather childish. The Cubs will not do any restoration work inside Wrigley Field until everyone agrees with their grand plans. It is like a kid on the playground upset with the scoring of his fellow players - - - so much so he takes his ball and goes home. It is like holding Wrigley Field hostage from itself. Even the most supportive Cub fan base question that tactic because they cannot understand why work on the public toilets, a new clubhouse and batting cage have anything to do with advertising signage or building a hotel across the street. Overreaching one's position is also risky: if your position gets to an absurd level, even supporters will turn on you.
The most current decision the team has made is to celebrate Wrigley's 100th anniversary with so much merchandising and special events that it makes all the talk merely white noise. It shows that ownership has continued to de-emphasize "baseball" as the foundation for coming to Wrigley Field. Wrigley Field is its own brand for special events, concerts, corporate outings, tours and other sporting events. It is being positioned not as the cathedral of baseball, but as an revamped entertainment complex like the Allstate Arena or United Center. It spanks of desperation to try to increase revenue at any cost. But that ties into the financial questions and decisions made above.
At this stage, all of the Cubs plans are one big crap shoot.
