By Dan Bernstein-
CBSChicago.com Senior Columnist

(CBS) How did such a weak-willed guy ever make so damn much money?

If the folks running the Shedd Aquarium had a sense of humor, they’d invite Tom Ricketts to be a part of their smash-hit jellyfish exhibit, floating in the mesmerizing, mysterious world alongside the sea nettles and moon jellies, staring blankly at passers-by as the collar of his oxford shirt flaps in the current.

As the Shedd’s official website says, “…they do it all without blood, bones, or brains.”

When Ricketts and his siblings took over the Cubs, he knew he needed to make significant changes to the baseball business, and he was not shy about telling people close to him about his plans. He researched successful models around MLB, getting a solid picture of what needed to be done and understanding that the executives he had in place did not fit his vision.

But something weird started to happen to Ricketts the more he hung around Wrigley Field. In the absence of any other baseball voice (team President Crane Kenney is as unqualified for his position as any in pro sports, perhaps ever) Jim Hendry made the successful case for his retention as general manager.

He smooth-talked Ricketts into believing that the horrible contracts were only at the behest of the previous owners, and, later, that the Cubs’ 24-13 record under interim manager Mike Quade was indicative of the “real” team, and they would be ready to pick right up where they left off in 2011.

We know how that worked out.

As this year’s squad went into the tank, sources close to the Cubs indicated that Ricketts again was getting up the nerve to make the moves that should have long been made. More moments of clarity allowed him to shake the silliness out of his head long enough to realize that this, now, finally, was enough.

Now, however, the Cubs ran off an improbable, seven-game winning streak last week, providing another chance for Hendry to put on his turban, pull his magic amulet out of his desk drawer and swing it in front of Ricketts’ eyes, telling him to believe the wins, and not the losses. Forget that they’re out of contention, with Baseball Prospectus still calculating a 0.0% postseason chance – here, once more, are the competitive Cubs to believe in for 2012.

It’s a stretch, I know, but I rule nothing out with this dude.

Ricketts has a history of foot-dragging as an owner. He even dithered with business he knew, when he started Incapital LLC to use the internet to package and sell corporate bonds. According to a 2002 article in Forbes entitled “At a Standstill,” Ricketts “…wasted nine precious months during 2000” while his old employer launched a similar program.

“There was an opportunity cost there,” he told the magazine, “I just wouldn’t be able to quantify it.”

“Try $1 billion worth of business – or more,” the article said. ”He ended the year having sold $5.3 billion worth through a network of 200 brokers, handing them (his old firm) roughly 80% of the $53 million in underwriting fees and giving Incapital a tiny profit on revenue of $12 million. But a guy of his pedigree – given his ties to brokerages and his prior record, not to mention his father, Joseph, who founded discount broker Ameritrade – could have done better.”

Sobering stuff, when you consider that October will mark two years of his Cubs ownership with no change whatsoever in the higher baseball offices (save for the addition of SABR-wonk Ari Kaplan, who was quickly pushed to the margins by the dinosaurs and remains there).

To this point, the default position for Ricketts as decision-maker has been inertia. The only opportunities he’s grabbed have been the ones provided by false hope, allowing him to avoid the angst of tough calls and bold strokes.

Nervous fans hope it’s not happening again.