By Bruce Levine–

MESA, Ariz. (CBS) – Nowadays, being the owners of the champion Cubs is considered really cool, but that wasn’t always the case for chairman Tom Ricketts and his family members. The Ricketts clan went through some tough and humbling periods after purchasing the franchise for $845 million from the Tribune Co. in 2009. The estimated worth of the Cubs is now more than $2 billion.

“It is certainly cooler after you win,” Ricketts said Saturday after talking to the team at spring training. “There were a couple years that were not as cool, though I still had a good time. It is just a great feeling.

“We are all blessed to be a part of something that means so much to so many people. This offseason was so incredible. We do have to turn the page and look at 2017 now.”

Every spring training, Ricketts has given a speech to the team and coaching staff as camp begins. As part of that conversation, he would tell the players what he expected of them as representatives of the Cubs. And at the end of each year’s speech, Ricketts would tell the team he expected them to win the World Series that season.

The media would smile and chuckle after hearing that six straight years from the confident Ricketts. Nobody is laughing now. In 2016, it finally came true.

“We are trying to be the best organization in sports,” Ricketts said. “We have to look every way to get better. We need to do that every way we can. Obviously, it gets better when you win. That creates more marketing flexibility and sponsorship opportunities. We just try to get better every day.”

That’s been the goal of the Ricketts family since taking ownership in October 2009.

“Our No. 1 goal is to win a World Series for this great fan base,” Ricketts said then. “We will build a winner.”

That became a reality through Ricketts’ action, not his words.

Ricketts made a smart move by retaining Crane Kenney as his top business executive. With Ricketts, Kenney helped diagram a plan to bring in a new baseball boss to replace general manager Jim Hendry. At the top of that wish list was Theo Epstein, who had helped the Boston Red Sox break their long championship curse and win titles in 2004 and 2007. The timing of the changes was perfect. Hendry was fired in August 2011 and Epstein, dealing with a huge collapse of the 2011 Red Sox, was made available by Boston that October.

Throughout a tough first three years of the Epstein era, the Cubs were bad on the field. The infighting with the rooftop owners and city of Chicago was ugly. Seeing a blue-sky finish to the grand plan looked bleak.

Now eight years after the purchase, Ricketts looks like a genius and pending grand landlord of Wrigleyville. The city is now a partner of the Cubs in heavy construction mode. Ricketts LLC controls 11 of the rooftop businesses.

Ricketts has had a lot of satisfaction from the historic 2016 season his team put together.

“One thing about the Cubs logo right now is it doesn’t stand for the years of not winning,” he said. “All of that stuff is behind us now. There is no more (negative) history to worry about, no more goats and that stuff. I hope that with continued success, we will make that ‘C’ into a symbol of winning. Not a symbol of not winning, like it was.”

Ricketts confirmed that the 1060 Project at Wrigley Field should be complete by 2020. Major League Baseball has yet to award the 2020 All-Star game to any franchise, so the Cubs should be an obvious favorite for that year. The team hasn’t hosted the Midsummer Classic since 1990.

“I don’t think it’s inevitable,” Ricketts said about the Cubs being a favorite. “I do think it would be a great for the league. It would be great for the game. It would be great for Chicago to have it at Wrigley Field. There is a process we have to go through. Hopefully someday soon (MLB commissioner Rob Manfred) will give us the nod.”

Bruce Levine covers the Cubs and White Sox for 670 The Score and CBSChicago.com. Follow him on Twitter @MLBBruceLevine.