The Political Giant That San Juan's Mayor Took On Before Trump - OZY | A Modern Media Company


Because breaking big sometimes entails putting yourself forward for the job no one else wants.

By Sean Braswell

San Juan Mayor Carmen Yulín Cruz’s debut on the world stage was unforgettable. “We are dying here,” Cruz said in a Sep­t. 29, 2017, press con­fer­ence after Hurricane Maria ravaged Puerto Rico and a slow, inadequate response from the U.S. federal government compounded the disaster. “So I am done being po­lite.”

Cruz, now 55, was bold and defiant. But it was far from the first time. Five years before she found herself standing up to President Donald Trump, Cruz, whose remarkable journey to power is the subject of this week’s episode of Breaking Big, airing at 8:30 p.m. EST Friday on PBS, was challenging another giant — one of Puerto Rico’s most established political bosses — in order to win her current job. 

Puerto Rican society, including its political life, remains defined by a machismo culture that can make it daunting for women to pursue their dreams and ambitions. As Cruz tells OZY’s editor-in-chief Carlos Watson, “If a man raises his voice in the Congress, he’s being vocal. You are being hysterical.”

Running on a platform of inclusion and change — and building a coalition of students, women and LGBTQ voters — the under-5-foot-tall Cruz billed herself as “La Pitirre,” a tiny but aggressive bird.

And in San Juan, the embodiment of that machismo culture for years was its mayor, Jorge Santini, a bombastic political strongman with slicked-back hair who ruled over the island’s capital for 12 years and had a reputation for wasting public money on extravagant projects. Cruz, a graduate of universities like Boston University and Carnegie Mellon, returned to Puerto Rico in the early 1990s to start her own career in politics, working under Sila María Calderón, Santini’s predecessor as mayor of San Juan and the first woman to become governor of Puerto Rico. Cruz ran for office herself in 2008, winning a seat in the Puerto Rico House of Rep­re­sen­ta­tives.

Four years later, the candidate from Cruz’s Popular Democratic Party had to drop his challenge to Santini when he became embroiled in a controversy over domestic abuse. The party was scrambling to find a last-minute replacement — but nobody wanted to challenge the powerful Santini, already serving his third term in office. Well, almost nobody. “So I’m saying, ‘Pick me. Pick me. I want to do it,’” says Cruz. “Well, my party had meetings and meetings and was like, ‘Anybody but Yulín.’ And finally, there was nobody left.” 


So Cruz got her shot. Nobody thought she had a chance against Santini. “I went to talk to her and said, ‘Listen, are you sure you want to do this? There’s no possibility that you’re going to win this election,’” says Charlie Hernandez, an attorney and the former majority leader of the island’s House of Representatives. “And she said, ‘I know I can win, and I will win.’” Cruz’s campaign director, Cesar Miranda, says she started with just two people on her campaign and zero money. But after watching Cruz in action, it was clear to Miranda and other political veterans that they had a candidate who would not require much polishing. “We said, ‘Let’s not touch this woman. She’s a wildflower. You don’t touch wildflowers.’”

Santini, known as “the Hawk,” mocked his opponent’s gender and experience on the trail, addressing her not by her name but as “esa señora” (“that woman”). Running on a platform of inclusion and change — and building a coalition of students, women and LGBTQ voters — the under-5-foot-tall Cruz billed herself as “La Pitirre,” a tiny but aggressive bird (the gray kingbird) that is the subject of a well-known saying on the island: A cada guaraguao le llega su pitirre (“Every hawk has its pitirre”). Wearing a red bandanna like a political revolutionary, Cruz took to the streets, launching a grassroots campaign dedicated to job creation, transparency, the needs of the poor and connecting with everyday Puerto Ricans. “She can convince. She can talk to people,” says Hernandez. “She is a political monster because she can find a way to do things, to convince the people.” 

And on Nov. 6, 2012, Cruz pulled off a David-beats-Goliath victory over the once-mighty Santini, beating him by around 6,000 votes. “The girl triumphed over the hawk” read San Juan’s El Nuevo Día the following day. “Our machismo culture in Puerto Rico resists a strong-willed, smart woman like [Cruz]; of course they do,” says Hernandez. “I’m still amazed at the way she did it.”

The day of her inauguration, Cruz ditched her red bandanna for an all-white outfit meant to send the message that with her at the helm, the residents of San Juan would be getting a clean slate. But, as San Juan realized when Hurricane Maria hit, a fresh start does not mean that Cruz fights any less hard than the men who have traditionally ruled the island. “I fight like a man,” says La Pitirre herself. “And I’m telling you this in the machismo context: I’ll give it to you as hard as you give it to me.”

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