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At a young age, Cynthia Roxas-del Castillo has already defied conventions expected of a woman . Now in her mid-sixties, she shows no signs of slowing down. Photo by Mike David

Breaking the mold

Contrary to the tense atmosphere prevalent in the Law School, there is a placating feeling of serenity while sitting through the Civil Law Review class of Dean del Castillo. It’s not because the workload is light or undemanding; in fact, it gets so complicated, especially when you have to interrelate the numerous legal concepts that have piled up through the years. But the moment Dean del Castillo opens her mouth, the disordered thoughts recedes, and everything starts to make sense. Unlike most professors, who feed on the fear and trepidation of students, she earnestly showers the class with motherly care and affection—without losing sight of the business of imparting knowledge.

Such is how Cynthia Roxas-del Castillo has perfected her craft. She gets the work done, without having to overdo it.

Her peers and superiors have early on recognized Cynthia’s potential. “I started teaching early,” she shares. Fresh from emerging as Class Valedictorian of ALS Batch 1976, she immediately got an offer from former ALS Dean Pompeyo Diaz to take over his Persons class. “Dean Pompeyo Diaz likes the girls, and there was no lady professor teaching yet. He said, ‘Why don’t you teach?’” And the rest was history.

She has been teaching Civil Law ever since; but in reality, Commercial Law is her bread and butter. “I am a business and corporate lawyer. My specialty is really securities regulations, so I do a lot of corporate fundraising and IPOs. I structure deals and acquisitions. I deal a lot with banks. That’s the typical work that I do.”

Cynthia eventually developed a passion for teaching. “I like working with young people,” she jests, saying that it makes her feel young. After ten years in the academe, she was designated as the Law School’s Consultant for Student Affairs, from 1987 to 1990. It did not take long until she assumed the deanship, a position she had held from 1990 to 2000. Not only was she the first female to be named as Dean—she also enjoys the distinction of being the youngest to hold the post, having been appointed just when she entered her forties.

Her biggest breaks actually come in pairs. Just when she began to teach, she also started to work as an underbar at Romulo Mabanta Buenaventura Sayoc & De Los Angeles. She quickly ascended the ranks; as fate would have it, she was named as a partner of the firm almost at the same time when she got appointed as Dean. And during her law school days, she was both the second female to become Class Valedictorian and editor-in-chief of the Ateneo Law Journal, next only to Isabelita Tapia-Paterno, who came five years ahead of her.

Given her stature, one could just imagine the relative ease of being a female lawyer in our once-patriarchal social order. So it seems.

Gender struggles

A young Cynthia Roxas entered law school right after finishing college. She got her degree in Political Science from the University of Santo Tomas, where female students were admitted since the 1920s. In contrast, Ateneo embraced co-education much later. Cynthia belonged to one of the first ALS batches with female members. However, when she was a freshman, the Ateneo School of Arts and Sciences (the forerunner of today’s Loyola Schools)—where most ALS students originate—was still an all-male institution. It was only a year after, in 1973, that the college unit of the Ateneo had begun to accept female enrollees.

Though not necessarily a big issue in law school back then, there were some hints of chauvinism. “It was parang, ‘What business do you have coming to law school?’ In fact you had to overcome then the impression that the reason why you’re in law school is that you’re looking for a husband. There were talks like that,” she laments. “The men think, ‘What are you here for?’”

She even jokes that the usefulness of the girls that time was only in terms of making digests. “Ang madaya sa boys namin, they only photocopied the girls’ digests! We said, ‘No, you have to do your own digests.’ ‘No, ‘coz you do it better,’ [the boys retorted]. So, that was our usefulness to the class that time. It was the girls who were matiyaga to do digests.”

To overcome these predispositions, she recalls that most female students had to act like a man. “When I went to law school, it was very much dominated by men. In fact our classmates said we all look like men!” But being the idealistic woman that she is, Cynthia refused to be labeled. “I like to look like a woman,” she emphatically declares.

In fact, this might have sparked Dean del Castillo’s interest in fashion. “Those days, not like your time today, the women had to struggle for recognition. And to do that, the stereotyped good lawyers actually acted, and looked, and sounded like men. As my friends will call them, the amazonas. It’s not what I wanted. I wanted to be good in the profession, and at the same time I wanted to continue looking like a woman. So I guess that’s why I make it a point to dress up, even for class.”

She seems reassured when asked about the existence of gender discrimination in the legal profession today. “Actually I think the women are favored nowadays. [The boys] are now the minority,” she relates. “I guess because women do it better in the sense that they are more studious. They can keep still longer than you guys can. Even in practice, they are now realizing that. Parang if you need somebody who will be there at all times, look for a woman. Because sometimes the men, I don’t know what they do,” she says with a chuckle.

If there is any consolation, she admits that the early struggles may have made the early female Atenean lawyers stronger. “I think we are made of sterner stuff,” she asserts.

Powerhouse couple

Although she detests the notion of women pursuing law merely to find husbands, she herself found love in the hollowed halls of Ateneo’s Padre Faura campus—the first home of the Law School. But it was not until reviewing for the Bar examinations that romance blossomed.

She married her classmate, the soon-to-be Supreme Court Associate Justice Mariano del Castillo, in February 1979, two years after passing the Bar. Truth be told, she was supposed to take her Master of Laws abroad, having had an acceptance letter already. But in her case, love got in the way. In a way, the Del Castillo couple best exemplifies the long-lost view that affairs of the heart do not necessarily have to take a backseat in favor of professional development—a common pitfall among today’s career-centric generation.

Being the wife of a high court justice does not really bother Mrs. Del Castillo. After all, her husband has been in the judiciary for quite some time already. “In the house, he’s like any other husband,” she shares. “I didn’t really have to adjust to anything. Of course there are some formal and social obligations I have to do now as his wife; when before, it was him who has to do a lot of social obligations because he was my husband. But now because he’s in the Supreme Court, I have to be in the women’s circle of the Supreme Court. I have to accompany him in certain functions. That’s the only thing that changed actually.”

There was a certain tinge of satisfaction in her voice upon revealing that her husband still drives for her. Like most couples, they still hold each other’s hands. “You don’t even stop doing that even in later stages of your life. Because at some point, that’s the only thing that you can do,” she muses.

However, Dean del Castillo gave potential law school couples a piece of advice. Their romance might have blossomed during Bar review, but she does not recommend it. “Dapat kasi when you’re taking the Bar you’re settled na. Or if you’re not, wait after. But it’s always better that he is also taking the Bar with you. Your date nights are study nights,” she says.

Fortunately, their respective careers have not posed any conflict of interest so far. “If it’s a Romulo case, he has to inhibit. That’s automatic in the Court. They don’t even include him in the raffle of Romulo cases. And because I don’t really do litigation, it does not pose a problem for me.”

The Del Castillo couple was blessed with two children, who eventually followed the footsteps of their lawyer-parents. However, given Dean Cynthia’s many responsibilities, she had to make certain sacrifices. As such, given a chance to redo something in the past, she would have wanted to spend more time with her children.

Price of success

As it is with most successful people, dreams are not achieved overnight. She admits that there are certain tradeoffs, in exchange for the things she and her family are enjoying right now. “I didn’t realize it much later, that somehow, the family suffered. Before, I thought it was not a problem. I came home late; my children didn’t see me often. But later, you just realize that you took away a few hours each that you could have devoted to them. So it’s a sacrifice,” she confesses.

Not everything was smooth sailing. The lowest point in her life was when she lost her daughter, back in 2008. “It was so difficult,” she admits.

Eventually, Dean Cynthia was able to pick up the pieces. Despite her shortcomings, she remains optimistic. “You have to give up some because I don’t think you can do everything. While family life is something that’s very vulnerable, you can do it. Many years ago, I used to say, it’s just a matter of trying to allocate time for each. But somehow, something’s gotta give. You only have 24 hours in a day.”

That is why she thinks that present-day career women should be held in high regard. “You have to give it to the women who are dedicated to their careers because they have to give up a few hours each day that they could have devoted to their children,” she says.

The most challenging cases she ever handled do not concern complicated questions of law, but rather involves strained family relationships or bitter squabbles among the parties. “It’s difficult because parties are not civil to each other; but otherwise, even the most difficult corporate restructuring, there’s always a solution to that. When people do not see eye-to-eye anymore, it clouds their judgment.”

If being a partner in a big and reputable law firm is difficult enough, imagine if you mix this with the administrative nightmares of heading the country’s best law school. She was just appointed as Dean (and firm partner) when the Lenny Villa incident happened.

In fact, she considers it as her baptism of fire. “There were pressures from all sides. The frats were after me; Loyola was after me. I had difficulty also because I was coming home late, so my husband and my family were also after me,” she relates.

Adding to the stress was the fact that her husband is a member of the Aquila Legis fraternity. “One time we had to go to Loyola and they had to interview him. There were pressures for him to resign. At the same time, the Aquilans were after me. ‘You’re the wife of an Aquilan, why are you doing this?’ So it came from all sides.”

However, she did not let the pressure get the best of her. “We had to be very strict. In fact it came to a point that people from Loyola wanted to shut down the Law School. I had to appear before Loyola. They even had this town hall meeting. I had to answer angry college students, [who were alleging that] the Law School is giving us a bad name,” she recounts. “But we had to do it with a firm hand, so we had to dismiss 30 or 40 of them. I’m not sure about the number. They filed cases against us. I had to go to trial. I had to testify. [Those were] difficult years.”

Fashion icon

In spite of the trials she faced, Dean del Castillo managed to overcome them seemingly unperturbed. It is probably because she chooses to distract herself with the lighter side of life.

Running remains to be one of her passions. She likes to run around the village every morning to keep her fit and healthy. She is also an accomplished runner, having participated in running events in Baguio and Siam Reap, Cambodia. Besides, the sport also serves as her bonding activity with her sisters. “We like to go to Westgrove to run because it has a lot of trees and it has a nice clubhouse. We can swim afterwards. We go [there generally] on a Sunday and have lunch in Tagaytay,” she narrates.

But more than anything else, Dean del Castillo seemed to have mastered the art of dressing up. Therefore, it is no longer surprising that students not only admire her for her academic brilliance, but also for her exquisite fashion sense.

“I just like to look good,” she says in response to the compliment. “Even in law school, I probably was different because I came to class more often in dresses. I had an aunt who liked to make my dresses. At that time, the uso was micro miniskirts. And the few girls who came in dresses, every time we climb the stairs, we had to put a book [to cover our] backs,” she recalls with a laugh.

Every time she steps into a room, her lovely getups always translate in garnering everyone’s admiration. “I stick to the basics. I like to look my age. I don’t like people who try to look younger than who they actually are.”

Dean Cynthia does not have a strict preference for particular brands. “I don’t really have favorites. I do have a number of LVs (Louis Vuitton) in my aparador. I like YSL for bags. [For shoes], I have LVs but I don’t find them comfortable actually. It’s a struggle to wear them from morning ‘till night. But I like the Fendi, they’re very comfortable. And Bally, surprisingly. I guess you have gamay-gamay, depending on the shape of your feet. A lot of people like Ferragamo, but I hate Ferragamo,” she says with amusement.

“I have Louboutins but I wear them only for special occasions because I can’t wear them from morning till night. After about four or five hours, they already hurt. They’re good to look at, so for parties, yes.”

But if given a choice, she would pick bags over shoes anytime. “Because the shoes, they get worn out easily, and they get replaced in the fashion sense quicker than the bags. The bags are classics. So I can do with less fashionable shoes, but I’d like to have the bags. Maybe it’s our security blankets. The shoes kasi sometimes, you can go with flats or flip-flops; but you can’t go without your bag.”

Most of Dean del Castillo’s daily clothes are bought ready-to-wear. However, for formal occasions, her go-to designer is Los Angeles-based Oliver Tolentino, who also makes dresses for some Hollywood A-listers.

She has a ready answer for anyone who balks at her fashion choices. “I don’t have any vice except that. I don’t drink. I don’t smoke anymore,” she quips. Naturally, she has a big walk-in closet—in fact, one whole room—where her husband is off-limits.

She expresses her delight over current trends, especially with how current law students dress up. “Now, I think fashion is back. Because in the 70s, it was a no-no to be fashionable. People can walk around in jeans and t-shirts, and that was the fad. Now, even in law school, the girls wear dresses. Before, they all wore pants and jeans,” she recalls.

“Our male classmates would say, “Mukha kayong mga lalaki eh.” ‘Coz people didn’t dress up. There were only a few girls in law school and they didn’t even fix themselves. But now, wow the girls are very fashionable! Sometimes, even more fashionable than required. Because they come in party dresses sometimes! But if you are a girl, enjoy it! Don’t try to look like the men!”

Just like in her law practice, Cynthia has been topping herself every year in terms of fashion. However, she concedes, “It’s because I’m getting old, so I have to put more effort.”

Taking the lead

Basing from her wealth of achievements and experience, it seems that age and time have treated her well. No what ifs, no wasted opportunities.

Thus, she urges young people to do the same. “These are the best years of your life. You have to enjoy it. I mean, the little times that you can have for yourself, go!”

Recognizing that being competitive is in the nature of a lawyer, she likewise gives a fair warning. “Per se, I don’t think it is bad. But when it consumes you, to the point that you’re willing to do anything to reach whatever goal you wanna reach, that’s bad. But being there to compete, being good at your craft… as long as you don’t try to put down other people, that’s fine. Basta wala yung crab mentality where you want to go up and pull others down. But if you wanna compete, go compete.”

Even at this point of her life, Dean del Castillo still imbibes this mantra. She shows no signs of slowing down. “I have more time now. That’s why I can spend more time doing other activities. Before it was difficult trying to balance everything. So now, I don’t have children to take care of, so more time,” she relates.

They say that some people are destined for success. It’s different in Dean Cynthia’s case. Success is in her nature. P

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