At 22, the Harford County native was already wondering what his own answer would be. He had cut a deal to have the Orioles pay for college if he didn't last in the majors, but what really fueled his curiosity was the thought that even stars retired with half their lives ahead of them."The way baseball is, if you're smart with your money and you make a lot of money, you have choices ... at the end of your career," Ripken says now, just shy of a decade since playing in his record-breaking 2,131st consecutive game.
"But still, the fact is, what are you going to do? How are you going to feel good about yourself? What contributions can you make? ...
"That," he said, "was always on my mind."
It's why he's busier now, four years after retirement, than he ever was as a shortstop.
As chief executive of Ripken Baseball Group, the 45-year-old multimillionaire leads a rapidly expanding baseball empire that boasts two minor-league ball teams, with a goal of owning 10 in a decade.
The empire also includes major-league-quality fields for young athletes in Aberdeen, with another complex under construction in South Carolina; books about playing baseball "the Ripken Way," and youth sports equipment with his name on it.
Ripken's ventures are a symbiotic mix of profit and charity, the two so intertwined that almost all the companies he endorses also support his nonprofit efforts.
He is carefully using his fame and good-guy reputation to strike highly focused deals on his terms, which often involve getting other people to help pay for his projects.
"When he played shortstop, he always positioned himself right," said Joe Geier of Geier Financial Group in Ellicott City, which handles the personal finances of Ripken and other baseball players. "To me, that's how he is in business."
Ripken's Baltimore County-based company is owned with another retired major leaguer, his brother Bill. It produces $15 million in revenue a year and several million in profits. By comparison, his last contract as an Oriole was worth a little more than $6 million.
Professional endorsers are a dime a dozen, but sports superstars who develop their own corporate concepts are not -- which is why Ripken stands out along with a few others, such as basketball icon Earvin "Magic" Johnson, who heads an urban revitalization development firm.
"It's a very rare fraternity of people who are parlaying their name into even bigger business opportunities," said David M. Carter, principal of the Sports Business Group in Los Angeles. "A lot have tried. Few have really succeeded."
Ripken's touch hasn't always been golden: In 1999 he bought 10 percent of the Baltimore BayRunners men's basketball team; it folded the next year because others were hesitant to invest. He once planned to start a restaurant called Cal Ripken's 2131 Club; the idea went nowhere.
Since then, he's focused on what he knows.
"Even now, ... when I try to solve a problem, I will try to put it in a baseball scenario," he said in an interview during last month's Cal Ripken World Series, a championship for pre-teens held in Aberdeen. "That helps give me comfort and confidence."
Ripken's employees say he looks over income statements, runs meetings, tweaks the design of new fields. While preparing for construction of the baseball complex in Myrtle Beach, S.C., called the Ripken Experience, he put a model of the site in his office to slide paper cut-outs of the fields around, trying different fits.
For the reproduction of Boston's Fenway Park at Aberdeen, he had a novel idea: Make the tall left field wall -- the Green Monster -- double as a storage shed.
"He thinks about ... how can you use buildings and functional things to add to the aesthetics of the ballpark," said Chris Flannery, Ripken's chief operating officer.
He runs ideas and finances past an advisory board that includes Ravens owner Steve Bisciotti and longtime agent Ron Shapiro. He dines regularly with Orioles owner Peter Angelos, who calls his former player "very imaginative and very thoughtful and very inquisitive." And he has the star power to schedule a chat with billionaire investor and baseball fan Warren E. Buffett.
"His approach is to know a lot of people," Angelos said. "He acquires knowledge through the normal process of socializing."
Ripken's youth baseball division grew out of clinics he taught with his namesake father and his brother Bill in the '90s. But his desire for a second career began to coalesce more fully in 1998, when the Detroit Tigers released his brother in midseason.
Bill Ripken needed a new direction. Cal suggested they meet while the Orioles were in Tampa Bay, Fla., to play the Devil Rays. Camped out in a hotel room, they laid the groundwork for a partnership.
"Youth baseball was a lot of that conversation," Bill Ripken recalls.
Now executive vice president of the company, he is heavily involved in day-to-day operations, particularly teaching, to give his more famous older brother time to play the door-opening role needed to win corporate support. He feels fortunate that his sibling was the sort to strategize about life after the majors.
"A lot of players are probably more along the lines of me -- `I'll deal with that when I deal with it,' " he said. "Cal always had an idea of what he wanted."
One of the things Ripken wants is to end the long slide in the number of people who play baseball.
The number of Americans who play the game dropped to fewer than 10 million last year from 15.5 million in 1990, according to the Sporting Goods Manufacturers Association. The bright spot is that an increasing number of children are playing competitively, the trade group said.
Ripken's company is built around that base.
This year 1,500 kids have attended Ripken camps, a 50 percent increase over last year, and 600 teams will play in Ripken tournaments from March through October -- nearly double last year. Fees range from $300 to $1,200 per child for the camps and $650 to $1,000 per team for the tournaments.
Almost all the activity is at his youth academy in Aberdeen, where kids swing and pitch on smaller versions of famous ballparks. "The fields are unbelievable," marveled Susan Knox of Mississippi, whose 12-year-old son played in the Cal Ripken World Series.
It has turned Aberdeen into a sports hub: Dorms and two types of Marriott hotels are in the works on the 50-acre academy site. Next door is Ripken Stadium, home of the IronBirds, a single-A affiliate of the Orioles.
Minor-league ownership was "purely an accident," Ripken says. His hometown's desire for pro ball sucked him in. But that has turned into one of the company's most reliable money makers -- the IronBirds have sold out each of their four seasons, a rarity in the industry. In October he'll take over the single-A Augusta (Ga.) GreenJackets, and he's recruiting major-league players to invest with him as he buys more.
The minors offer varied opportunities for profit -- from concessions and merchandise to events between games -- but Ripken said he appreciates the grassroots feel. It's affordable family entertainment, at $10 for an average ticket, he said.
"With minor-league baseball, you can reach into the community," he said. "I like the potential of that."
The big leagues aren't grassroots, but he's interested in owning a stake there, too. Overseeing baseball operations for a major-league team would let Ripken test his ideas "at the highest level," said his spokesman, John Maroon.
Speculation is high that he's considering buying a stake in the Orioles or the Washington Nationals, but Maroon said the right opportunity hasn't presented itself yet.
"I just don't know how you can keep the Ripken family out of Major League Baseball," said Shapiro, Ripken's former agent and current adviser.
The company has been branching out in other ways, adding a sports-business consulting arm, selling merchandise autographed by athletes such as Green Bay Packers quarterback Brett Favre, and striking a deal with Nike for youth baseball equipment with the Ripken company logo.
Indeed, Cal the brand is an important part of the business -- one that feeds the rest.
He signed a three-book contract this year after the success of 2004's Play Baseball the Ripken Way. He gets roughly 500 requests annually to give speeches, says Keppler Speakers, his representative. His fee starts at $50,000. As an endorser, he brings in several million a year for appearances on television, radio, billboards, even credit cards -- and his spokesman says he's more in demand now than as a player.
"Cal Ripken is a business unto himself," said Steve Rosner of 16W Marketing, which handles his endorsements.
Those deals are more than just ads. XM Satellite Radio also gave him a weekly show with Bill Ripken to talk about baseball. He represents credit card giant MBNA at conventions, executive dinners and charity events.
He made a surprise appearance at a large gathering of Comcast Corp. employees, and "the place went absolutely wild," said Jim Gordon, a spokesman for the cable company.
That might give him an advantage if he goes after Comcast's three minor-league baseball teams in Maryland, which were for sale last year before a deal fell through.
As the banner ads on the ball fields in Aberdeen show, most of the companies he represents also pitch in for his ventures.
They sponsor the Cal Ripken World Series, a championship event for the nonprofit Babe Ruth League, the youth baseball group that renamed its largest division for Ripken in 1999.
The companies finance the Cal Ripken Sr. Foundation, which brings baseball to disadvantaged kids. And the businesses also pay to be associated with the IronBirds.
Ripken plans it that way, leveraging his cachet as an endorser into deals that help his divisions, some of which haven't gotten beyond break-even yet.
"We look ... for more of a stable, long-term partnership where we can accomplish things together," he said.
He gets government in the game, too. South Carolina agencies have promised about $1.7 million in infrastructure improvements for the Ripken Experience project. In Aberdeen, he paid for a third of the $18 million stadium; the city, county and state picked up the rest.
There's grumbling in Aberdeen about this. Some residents think stadiums and tax money shouldn't mix, said city finance director Francis Bitzelberger.
City leaders call it a break-even proposition because admissions taxes from the stadium and lease payments on the land for the youth academy are covering their debt payments. They were expecting to pay for part of the stadium before Ripken got involved, when it was just a hope.
"We've been very blessed, I must say," said Aberdeen Mayor Doug Wilson. "He could have built this complex anywhere else, but he really wanted to do it in his hometown."
Don Morrison, who coached Ripken for three years at Aberdeen High School, thinks the larger point is this: In a city of 14,000 there sits a stadium that holds 6,100 -- and there's a waiting list to get in.
"Aberdeen is not a metropolis [by] any stretch of the imagination," he said. "To have a stadium and a complex like what he's building there and to have it filled every night to the point that you can't get a ticket. ... Think of all the hurdles that had to be overcome."
It fits with his memory of a boy with quiet determination and a consuming drive to win. "Nothing that he does surprises me anymore," Morrison said.
Sun staff researcher Jean Packard contributed to this article.
On the Web
Listen to reporter Jamie Smith Hopkins talk about this article at baltimoresun.com/2131.