To Shapiro, the answer was obvious. Of course, he was in attendance when Jimmy Buffett invaded the Indians' home stadium for a Cleveland concert in 1995. It was a big event at the time, and Shapiro would not have been anywhere else.
"Heck yeah, I was there," Shapiro beamed.
Back then, such an event at the ballpark was a bonus. The Summer of '95 marked the first of a five-year run to the postseason for the Tribe -- which was thriving in a new ballpark, and playing in front of capacity crowds on a nightly basis.
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Times have changed dramatically, though, both for the city of Cleveland and for the Indians franchise. On June 11 this year, the Tribe will hold an event called the "Indians Music Festival," inviting country music star Brad Paisley and his H2OII Tour to Progressive Field for the first concert at the stadium since Buffett came to town.
This time around, the event is another experiment within the Indians' attempts to find creative ways to boost revenue. Over the winter, the ballclub held an event called "Snow Days," which turned the stadium into a winter playground with sledding hills, ice skating and other attractions.
With Cleveland's population at a 100-year low and the Indians' attendance among the lowest in baseball, Shapiro is trying to find ways to simultaneously improve the product on and off the field. After nine years as the Indians' general manager, this is a whole new arena for Shapiro.
"I'm learning a ton every day," Shapiro said. "The challenge is big."
Shapiro does not want people to get the wrong impression, though. Events such as the "Indians Music Festival" or "Snow Days" are not taking priority. First and foremost, Shapiro and new general manager Chris Antonetti want to build a franchise that can have a sustained period of winning.
As much as Shapiro is enjoying his new role as president, he is a baseball man first -- and he enjoys his frequent discussions with Antonetti about ways to improve the team. That said, Shapiro's new job description goes well beyond the chalk lines, and that is where he is doing all he can to locate additional funds for the franchise.
"You have to be aware of your challenges," Shapiro said. "And you've got to build a strategy that addresses those challenges. Part of our strategy is, how can we stay true to and serve our core fan? We've got to win. We've got to get a winner back on the field.
"So one part of the operation, the most important part, is how do we accelerate the baseball operations and accelerate towards winning as quickly as possible? We all recognize that's the most important thing. So we have to look for incremental gains.
"We have to find ways to bring new people to the ballpark, to bring people that can enjoy the experience and can enjoy the atmosphere, and can recognize it as unique and special, and may not have thought about coming there otherwise."
That is where concerts or offseason ventures come into play.
"It's taking advantage of our greatest asset," Shapiro said. "We feel like the ability to get different people into Progressive Field for events outside of baseball will ultimately result in more people coming to watch baseball, too."
This is not to say that the Indians expect every event to be a complete success.
Take "Snow Days," for example. The event drew more than 50,000 people over the offseason, but the Indians went into it understanding that the event would likely result in a financial loss. That is exactly what happened -- but that can often be the case when a one-of-a-kind event is held.
It was an experiment, and one that the Indians hope to turn into an annual offseason event that ultimately results in profit. The task now for Shapiro and the Indians' front office is to evaluate "Snow Days" and find avenues for improving its appeal, and discovering ways to convince fans to head downtown.
"There were so many unknowns," Shapiro said. "You're really creating an event from thin air that has never been done before. We went in there with a complete set of unknowns on many different levels. On most levels, it was a resounding success, but we need to make it even more successful next year.
"It's more just the attitude of, 'How do we drive more people to downtown Cleveland?' We recognize that for a lot of people it seems to be a challenge. There seems to be an obstacle of getting in the car, and driving downtown on a weekend and not a work day. So how to we bridge that?"
Earlier this month, 2010 U.S. Census figures were released. It is no secret that Cleveland has been hit hard economically over the past decade -- especially during the current recession -- but now there are raw numbers to show how dramatic the decline has been.
According to the Census, the city of Cleveland saw its population drop from 478,403 in 2000 to 396,815 in 2010 -- representing a drop of 17.1 percent. It is the first time since 1900 that the city's population dipped below 400,000. Cuyahoga County as a whole saw a decrease in population of 8.2 percent over the past decade.
"We've got to be creative," Shapiro said. "Our demographic challenges are real. The market is literally shrinking. We've got to get new people into the ballpark."
One way is by having Paisley and his country music entourage invade the stadium for a summer concert. Cleveland named the event the "Indians Music Festival" because it is not expected to be a one-time show. Shapiro hopes to have more concerts in the future with different varieties of music.
Without going into specifics, Shapiro also noted that he is currently discussing other potential events to be held at Progressive Field. He is also in the early stages of evaluating ways to improve the ballpark itself.
"We're doing a master-planning process, that's as much of a self-assessment as anything else," Shapiro said. "What areas do need improvement? We're progressing with that. Hopefully, sometime this summer we'll have some update as to what our plans are in that area."
Shapiro hopes that all these projects ultimately result in a better baseball team.
"None of these secondary businesses," Shapiro said, "are ever going to replace what's most important, which is baseball."