The man who would be king   

Updated: June 6, 2008, 4:18 PM ET

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Joe Molloy

Gary Bogdon for

Introducing Joe Molloy, phys ed teacher at D.W. Webb Middle School.

TAMPA, Fla. -- It's a warm, sun-drenched weekday morning outside D.W. Webb Middle School, in the Town 'n' Country neighborhood of Tampa. Under a cloudless sky, Joe Molloy, a boulder of a man, bespectacled and clad in a gray Webb Middle School T-shirt, khaki shorts and black New Balance sneakers, is preparing for his first phys ed class of the day. He's going to have his sixth-graders play kickball, so he's placing orange cones around the grass field to serve as the bases.

"They don't know how to set up the cones," Molloy laments to his fellow teacher, Timothy Ruff.

"That's what you're here for," Ruff replies teasingly.

A flock of students -- some wearing their gym-class attire, others who didn't bother to change -- surrounds Molloy, chattering at him as he puts the cones in the proper positions. He is trying to calm everyone down and get them to take their places. "OK, we'll play boys versus girls," Molloy booms. "Girls bat first!"

With that said, Molloy saunters to the middle of the infield, picks up a white volleyball and prepares to roll the first pitch toward home plate.

Joe Molloy

Gary Bogdon for

Joe Molloy, launching a pitch to one of his sixth-graders.

"Can we throw the ball at runners?" yells one of the boys in the field behind him. "Yes, but only below the waist," Molloy replies.

"Can I be the pitcher?" asks another boy. "No," Molloy says, sporting a sly grin. "I am always the pitcher, and I am always the umpire."

Standing there, watching him, it's hard to believe he also once called the shots for the most storied franchise in professional sports.

Flash back to 6 a.m., and it's still pitch-black outside, save for the twinkling of a handful of stars. But the lights are on at the Aguila Sandwich Shop on Hillsborough Avenue and the grill has already been fired up. It's the kind of joint you'd never discover as a tourist -- and if you did happen to find it, you probably wouldn't venture inside. But the food is a bargain, and first-rate. And Molloy is in his usual seat, at his usual table, enjoying his usual large decaf Cuban-style espresso and plate of ham, eggs, green peppers and onions.

Joe Molloy

Gary Bogdon for

Molloy arrived at Aguila while it was dark, but he was still there when the sun came out.

Molloy is surrounded here as well. Seated next to him is his friend Manual Duran, the principal of another local elementary school. Aguila's owner, Mario Aguila -- who has affectionately dubbed Molloy's table "The Professors' Table" because it's often full of teachers -- dotes on him all morning long. And another buddy, who simply goes by Mr. T, practically tackles Molloy on the way out, not wanting him to leave.

Molloy comes for the camaraderie -- and for one other reason. "They've got the best coffee," Molloy says. "Certainly in this city anyway."

He should know. He's lived in Tampa his entire life and has been coming to the Aguila, or its previous incarnation, almost every morning before work for more than 20 years. He came here when he started out after college as an elementary school teacher. And he kept on coming, even while on his magic carpet ride to the top of the New York Yankees organization.

During the past year, we've started to get to know Hank and Hal Steinbrenner, the two sons of Yankees principal owner George Steinbrenner. With The Boss' health deteriorating, Hank and Hal have assumed responsibility of running the organization. We've seen Hank, the older brother, exhibit the same blustery tone, impulsiveness and impatience of his father -- to the delight of many media scribes, and to the chagrin of some Yankees fans.

Joe Molloy

Gary Bogdon for

Mr. T wanted a picture, and he didn't want his buddy to leave.

But it wasn't inevitable that Steinbrenner's two sons would take over the franchise after their father relinquished the reins. In fact, Steinbrenner's son-in-law, Steve Swindal -- married to Steinbrenner's daughter Jennifer -- had been anointed the heir to the throne, until the couple divorced last year.

What most people don't know, or at least don't remember, is that many years ago The Boss groomed another son-in-law, married to his other daughter, Jessica. Not only was this man the heir apparent, he was actually at the controls of the franchise during one of its most pivotal years of revitalization.

Right now, that man is polishing off his coffee, before driving over to Webb Middle School to play kickball.

Joseph Anthony Molloy was born on March 13, 1961, in Tampa. His parents divorced when he was very young, and according to the settlement, his father was not allowed to see him afterward. He was raised by his mother, Cynthia, and her second husband, who adopted him.

Molloy's mother, of Cuban-Lebanese descent, was a public school teacher for 35 years, while his adoptive Irish father, Robert, worked at an Anheuser-Busch brewery. Molloy is their only child. "It was a very loving, caring family," he says. "We struggled, just like any other middle-class family. But you pull together and make it work."

Molloy attended Catholic schools his entire childhood: St. Lawrence Catholic School and then Tampa Catholic High School, where he was elected student body president. During his high school years, Molloy felt a calling to the priesthood. Inspired by the Franciscan brothers who taught at Tampa Catholic, he decided to enter their seminary in Brooklyn, N.Y., after graduation.

He spent six months in the seminary before deciding he wasn't ready for the priesthood after all. But he still wanted to be a teacher, so he moved back home to Tampa and completed a college degree in physical education. He was then hired to teach science and phys ed at St. Lawrence.

George Steinbrenner

AP Photo/Peter Cosgrove

Imagine getting set up with one of George Steinbrenner's daughters?

During his third year there, he was set up on a blind date by Carmine and Barbara Iavarone, friends of Molloy's parents. Carmine Iavarone also happened to work for George Steinbrenner, and he thought Molloy would be a great match for Jessica Steinbrenner.

Molloy was intrigued, even though he didn't know George Steinbrenner owned the Yankees. The name sounded familiar, but Molloy wasn't a huge baseball fan. "I was actually talking to my parents at one point, and they told me, 'Well, you do know that [Steinbrenner] owns the New York Yankees,'" Molloy says. "And I was kind of like, 'Uh, OK?'"

Their first date was at the Hall of Fame Bowl on Dec. 23, 1986, at Tampa Stadium. Jessica was the chairperson of the welcoming committee; her father was a financial backer of the game. "We never really watched much of the game," Molloy says. "We kind of just sat in the back of the luxury box and talked all night."

It was a whirlwind romance. Three months later, after asking George Steinbrenner's permission, Molloy gave Jessica an engagement ring on her birthday. And they were married on Nov. 7, 1987, at St. Patrick's Cathedral in New York. Cardinal John O'Connor celebrated the Mass, and among the 100 attendees were Donald Trump, Lee Iacocca and Howard Cosell.

George and Molloy hit it off quickly, too. Molloy, in addition to teaching, was also coaching St. Lawrence's basketball team. George would sometimes attend his games, yelling at the referees and then wanting to talk strategy with Molloy afterward.

But George also extended Molloy an opportunity for a new job. "George had said to me, 'Do what you would like to do. If you wanna come on board the family business, you certainly can,'" Molloy says.

Molloy could have picked any of Steinbrenner's many business ventures to join. But he figured he'd take advantage of his sports background. So after finishing up the school year, Molloy went to work for the Yankees full-time in the summer of 1988. He traveled around the country to the Yankees' minor league affiliates, basically taking a crash course on the entire organization. He began assuming more and more responsibility with the franchise, particularly its minor league operations, and he eventually rose to the position of vice president.

Little did he know, his role was going to be even bigger.

On July 30, 1990, commissioner Fay Vincent banned George Steinbrenner from Major League Baseball for paying a known gambler to collect dirt on Dave Winfield, with whom Steinbrenner was having a financial dispute.

The Yankees had to appoint a new managing general partner.

Steinbrenner first asked his eldest son, Hank, to take over, but Hank wasn't interested in the job at the time. His other son, Hal, was still in college. Limited partner Robert Nederlander, a theater owner, took the reins for 16 months before resigning at the end of 1991. Daniel McCarthy, a Cleveland attorney and also a limited partner, then took over on an interim basis, but he was ultimately rejected by the commissioner.

So in early March 1992, at the ripe old age of 30 and four years removed from being an elementary school teacher, Joe Molloy was chosen to become the new managing general partner of the New York Yankees.

Joe Molloy

Gary Bogdon for

Molloy and Gene Michael were the ones who hired Joe Torre.

"I was honored that [George] would turn to me," Molloy says. "I told him that I would do everything under my power to make sure that the family was always well-protected."

A change in philosophy was already under way in the organization at this point. With Steinbrenner absent and Nederlander largely keeping his hands off the baseball side of the business, the Yankees' baseball staff -- led by general manager Gene Michael and also including current San Francisco Giants GM Brian Sabean and current Yankees GM Brian Cashman, among others -- was able to go about building the team in a different way. For years, the Yankees had made a habit of trading away their top prospects for established veterans, many times getting the short end of the deal. Years of bad trades and poor free-agent signings finally caught up to them when the Yankees finished in last place in 1990 -- the first time that had happened since 1966. Michael & Co. wanted to take a different approach: They wanted to hold on to young talent like Bernie Williams and minor leaguers like Jorge Posada, Andy Pettitte and Mariano Rivera, and build the team via the farm system.

That continued under Molloy's watch. He listened to his baseball experts and was also a proponent of that philosophy. "We kinda took advantage while George was gone and put the money into player development and scouting," Molloy says. "In '90 or '91, I commissioned a little study. At the time, there were 52 players on other teams' 40-man rosters that were originally drafted and developed by the New York Yankees. So we were doing something right, but there was never the opportunity to see the fruits from the labor."

Derek Jeter

AP Photo

With Molloy's approval, the Yankees drafted Derek Jeter with their first-round pick in 1992.

Two extremely important moves were made with Molloy's blessing in 1992: trading outfielder Roberto Kelly for Paul O'Neill in November and signing starting pitcher Jimmy Key in December. But the most important thing Molloy did while in charge of the Yankees? He green-lighted the signing of a young shortstop named Derek Jeter.

Jeter was regarded as one of the top prospects -- if not the No. 1 prospect -- available in the 1992 amateur draft. But his agent was looking for a $700,000-plus signing bonus, and many teams weren't willing to pay that much at the time.

The Yankees had the sixth pick in the draft, and their scouts thought Jeter might still be available. So they asked Molloy if he'd be willing to spend that kind of money.

Molloy had some concerns. Jeter was a high school player, and he knew Steinbrenner preferred drafting college players because they were further along in their development and more likely to make the big leagues quickly. But Molloy ultimately deferred to his scouting department. "I told them, 'OK, if [Jeter] is there, if you guys want him, we'll take him,'" Molloy says.

Molloy was generally well-regarded in the Yankees organization, despite not being a baseball lifer like many of the other front-office personnel. "He knew what his strong suits were, and what they weren't," says Mitch Lukevics, the current director of minor league operations for the Tampa Bay Rays, who served in the same capacity with the Yankees during Molloy's tenure. "When he didn't know something, he asked a lot of questions. He listened to a lot of opinions, and made educated decisions.

Legends Field

Gary Bogdon for

Legends Field -- which was renamed George M. Steinbrenner Field earlier this year -- is the Yankees' spring-training home, and where the owners' offices are. Joe Molloy was largely in charge of its construction.

"Bottom line, he gave us the necessary resources to do the job. Joe was terrific to all of us."

According to both Molloy and Lukevics, this was no puppet regime under Steinbrenner. While Molloy had plenty of contact with Steinbrenner during family situations, the two were forbidden to discuss baseball matters. Molloy says he stuck to the commissioner's ruling.

Steinbrenner was reinstated on March 1, 1993, and he assumed official control of the Yankees again. But Molloy remained a general partner and continued to play a major role in the day-to-day operations of the organization. He personally negotiated Tino Martinez's new contract when the first baseman came over to the Yankees from Seattle before the 1996 season. He spearheaded the construction of the Yankees' new spring training complex, Legends Field in Tampa, which opened in 1996. He even approved the idea -- brought to him by members of the Yankees' groundskeeping crew -- of the groundskeepers performing "YMCA" when they raked the infield during games (a crowd favorite).

And along with Michael, he negotiated the deal that brought Joe Torre on board as the Yankees' manager in November 1995.

"Joe [Molloy] was a young man thrust into a very challenging position," says Lukevics. "Not many people his age could have done what he did. But the proof is in the pudding. He answered the bell, and he did a tremendous job."

As every baseball fan knows, the franchise continued to rebound in the years after Steinbrenner was reinstated. In 1994, the Yankees were in first place in the American League East and appeared to be a World Series contender, until the players' strike resulted in the cancellation of the World Series. In 1995, the team made it to the playoffs for the first time since 1981, before losing to the Seattle Mariners. And in 1996, the Yankees won their first World Series since 1978.

Yankees ring

Gary Bogdon for

Molloy's 1996 World Series ring -- one of only five like it.

After winning that World Series, George Steinbrenner had five special championship rings made, with bigger diamonds than even the rings given to the players and coaches. One was for Steinbrenner himself. The other four were for his two sons, Hank and Hal, and his two sons-in-law, Swindal and Molloy. During the ticker-tape parade down New York City's Canyon of Heroes, Molloy rode on the same float as Joe Torre and his coaching staff.

"It gives me goose bumps," Molloy says. "Still gives me goose bumps to this day."

Joe Molloy is sitting at his desk in Room 303H -- a small office directly off the boys' locker room -- leafing through progress reports between periods. Student after student wanders into the office, looking for a bottle of water, a dollar for the soda machine, or just to chat.

Joe Molloy

Gary Bogdon for

Molloy rarely gets a moment to himself in his office. Kids are always coming in and out.

Molloy has a smile, a fist bump or a sarcastic remark for each of them before sending them back to the locker room. After all, the office is barely big enough to fit Molloy's desk and the second one directly behind him. He shares this office with Ruff, his fellow PE teacher, who only recently graduated from college.

There isn't a stitch of Yankees memorabilia in the office. He doesn't wear his World Series ring. There isn't a single clue. But there is one picture on a shelf above Molloy's desk. It's of his four children -- two sons and two daughters -- in a frame that reads, "Dad -- you're the best" above and below the photo. And there's a quotation, typewritten in black ink on a yellow sheet of paper, taped to the office window. It reads:

"Our greatest glory consists not in never falling, but in rising every time we fall."
-- Oliver Goldsmith

Molloy's fall from the Yankees hierarchy was remarkably swift.

After spring training in 1997, for the second time in two years, Molloy checked himself into the Duke Diet & Fitness Center -- a well-known treatment center for obesity. His weight had ballooned as the stress that came with working for his father-in-law really started to wear on him. "George was very demanding as a boss," Molloy says. "He would not hesitate to chew your ass [out], just as much as the average employee."

When Steinbrenner would visit Molloy's family in the evening, it was more of the same. "[George] would stop by and spend, oh, 30 minutes or so with the grandkids, Jessie and I," Molloy says. "Then I would walk him outside and we'd talk a little bit more about what was happening [with the team]. It was tough."

In addition, George had begun to assert more and more direct control of the team again, leaving Molloy out of certain meetings and making him feel increasingly irrelevant. Molloy was forced to keep his frustration bottled up inside, unable to vent at the end of a long day. "Jessica said that she really didn't want to hear any of the stuff that'd gone on," Molloy says. "When I came home, it was all about home, and the kids, and her -- which I respected. But it was certainly a challenge."

While he was at Duke he realized he needed a break. That August, Molloy walked into George's office and told him he wanted to take a one-year leave of absence from the team and take a job teaching religion at his old high school, Tampa Catholic.

Jessica Steinbrenner

AP Photo/Kathy Willens

Here's Jessica Steinbrenner earlier this spring, with her father.

"[Joe's] a very religious young man," Steinbrenner was quoted at the time. "He asked if he could do this. How do I say no to God?"

But the problems didn't end there. Molloy's marriage to Jessica Steinbrenner deteriorated soon after he made his decision to step away from the Yankees. Molloy prefers not to discuss the details, but in January 1998 they separated, and in March he filed for divorce.

The couple eventually resolved things out of court, sharing custody of their four children. Molloy did receive a financial settlement, but he says he still needs to work to support himself.

The divorce is something that clearly still pains him 10 years later. You can see it in his downcast eyes and hear it in his hushed tone when he's asked about it. "I miss a lot of aspects of family," he says. "You don't ever walk into a marriage saying you're gonna get divorced.

"Sometimes it's just not in God's plan."

Joe Molloy

Gary Bogdon for

Molloy borrows another teacher's classroom every morning to take attendance of his home-room class.

Molloy officially resigned from the Yankees in February 1998. He has worked at several different schools around Tampa since, including a stint as principal at St. Patrick's Catholic School, where he says he was forced to resign after a disagreement over finances with the pastor of the parish.

Observing him interact with his students, you can't help but think you're watching a man doing exactly what he was put on Earth to do. Children surround him while he's on morning duty patrolling the courtyard before first period. They besiege him in the hallways or in his office between periods. And they beg him to play with them, instead of just supervising them, during his classes.

"He's like the Pied Piper, the way kids follow him around," Webb principal Brent McBrien says. "The kids are always hanging all over him. And no kids get mad at him, which is odd."

It is indeed startling. At a school where fights are common, students gravitate to him like he's Santa Claus. And even when he does have to scold them, he does it in a disarming way. It was no surprise to learn he shared the most popular teacher award this year, as voted by the students.

"The kids know that he sincerely cares about all the students, whether he teaches them or not," says fellow faculty member Susan Decker. "He's just special. And they know it."

Most people would consider going from running the Yankees to playing kickball with sixth-graders a major step down. But Molloy doesn't look at the world that way. Teaching was his first love. He knows he's good at it, too. While he comes across as exceedingly humble 99 percent of the time, every once in a while he'll let slip a comment which reveals a dash of pride.

Gary Bogdon for

Gary Bogdon for

Molloy doesn't just stand on the sideline. He often plays with the kids himself.

"I've just always had a really strong connection with kids," Molloy said in one of those moments. "[And] I can motivate anybody to do anything."

After watching him teach, you can't help but believe him.

Does Molloy miss working for the Yankees? Sometimes, he admits. He once approached the Tampa Bay Rays about working in some capacity in their front office. They didn't even return his call. He was disappointed, but he's moved on. "At this point in my life, I'm very happy with what I'm doing," he says.

He may not be a boss anymore, but Molloy still serves as a mentor to younger co-workers, like his officemate. Ruff will never forget that right after he was hired at Webb, Molloy showed up at a football game he was coaching, just to offer his new co-worker some support.

"He's taught me to make the best of situations, play the cards you're dealt, and just have a positive attitude," Ruff says. "He has an amazing heart. It goes on forever."

Most of all, Molloy remains devoted to his family, particularly his four children -- ages 14, 16, 18 and 19 -- of whom he's fiercely protective. He never remarried; in fact, he hasn't even dated since his divorce. He lives alone, in a townhouse in Citrus Park, just a few minutes away from Webb, spending as much time with his children as he can.

Molloy says his relationship with his ex-wife -- who has remarried and currently runs the Steinbrenner horse farm -- is good. And he says the same about his relationship with his former brothers-in-law, Hank and Hal. "We got along great," Molloy says. "And I still consider them friends."

As for his Yankees memorabilia -- pictures, jerseys, bats, etc. -- almost all of it has been packed away, at least for the time being. He gave away all his autographed baseballs to charity. The key to New York City he received after the '96 World Series is the only thing that remains on display in his home.

Joe Molloy

Gary Bogdon for

Molloy with some of his co-workers, including fellow phys. ed. teacher Timothy Ruff (directly to his right).

Molloy doesn't watch the Yankees play anymore, although he admits he checks out the New York tabloids on the computer every couple of days to see what's happening and sometimes daydreams about what moves he might make if he was still in charge. He's never gone back to Yankee Stadium. And he's rarely been to Legends Field (now George M. Steinbrenner Field), even though it's close to home.

But Molloy hasn't erased it all from his memory. Nor does he want to. Ask him about his Yankees days, and he'll usually stare into space for a few moments first, as if he's reliving some part of it in his mind. Then, more often than not, he'll smile.

"I would do it all over again," Molloy says. "I wouldn't trade any moment. The happy ones, the laughter … and I wouldn't trade the sad moments either. Because you grow from them. You grow from them all."

A few minutes after 4 p.m., after dismissing his last class of the day, Molloy closes and locks the door to Room 303H, and then begins to make his way across campus to exit the school.

Student after student calls out to him along the way. "Hi, Coach Molloy. … See you tomorrow, Coach Molloy. … Do you have a dollar, Coach Molloy? … Got any doughnuts, Coach Molloy?"

Joe Molloy

Gary Bogdon for

After a long day at school, Molloy was headed for his son's baseball game.

When he reaches the front entrance of the school, he says hi to a fellow faculty member and then approaches her very young son, who looks to be about 5 years old. He shows the boy his World Series ring, which he'd worn to school for the very first time.

Then Molloy says to the boy, "Hey, buddy. Do you know what this is? This is a World Series ring. And one day, when you grow up to be a big star and you win the World Series, you can get one of these."

With that, Molloy walks out the front door and into the parking lot, driving off to his son's baseball game. The district championship game was that evening, and he was heading over early to help sell tickets.

Joe Molloy isn't a big star anymore.

On second thought, maybe he still is.

Kieran Darcy is an editor for Page 2. You can reach him at


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