Alan Gross: Castro's prisoner
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    A Secretive Path to Raising U.S. Flag in Cuba

    A Secretive Path to Raising U.S. Flag in Cuba

    WASHINGTON — Before the United States and Cuba could seal a historic
    diplomatic rapprochement brokered in 18 months of secret talks, they
    first had to hide a pregnancy.

    Late last year, when President Obama and President Raúl Castro of Cuba
    were only weeks away from a stunning announcement that they were ready
    to end a half-century of hostility, White House officials negotiating
    the thaw learned of a problem that could derail their clandestine work.

    A surreal subplot to the negotiations — a covert plan to allow a Cuban
    prisoner held in the United States to artificially inseminate his wife
    in Havana — had succeeded. But the woman, who is famous in Cuba, was now
    visibly pregnant. White House officials found themselves in the bizarre
    position of pressing the Cuban government to keep her out of the public
    eye for fear that her appearance would raise suspicions and upend the
    talks at a critical moment.

    The story of America’s reconciliation with Cuba that culminates on
    Friday with the ceremonial raising of the United States flag over a
    newly reopened embassy in Havana is one of near misses, crossed wires,
    political stalemates, freelance interference and unexpected challenges
    that could have changed the course of history. While presented with a
    flourish to a surprised world, the path to a diplomatic opening was very
    nearly a dead end.

    Driven by the ambitions of a president eager to make a fresh start with
    a Cold War-era adversary and eventually blessed as a moral imperative by
    Pope Francis, it was fueled at crucial points by more human
    considerations: the mounting desperation of Alan P. Gross, an American
    government contractor jailed in Havana, and the wish of the wife of a
    Cuban man imprisoned in California to bear his child before it was too
    late. It was shadowed at every turn by suspicion and mistrust, calcified
    over decades.

    Uncertain Road

    The drive for reconciliation defied normal conventions, handled by just
    two White House aides who bypassed diplomats at the State Department. At
    one point in the summer of 2014, when White House officials feared that
    Mr. Gross might commit suicide in prison, Mr. Obama intervened directly
    by writing him a letter imploring him not to give up hope.

    “When we initiated the discussions, we didn’t know exactly where it
    would lead,” said Benjamin J. Rhodes, the top Obama aide who, with
    Ricardo Zuniga, the National Security Council’s top Western Hemisphere
    official, spent more than a year sneaking off to secret negotiations in
    Canada and finally at the Vatican. “The talks frankly ended up leading
    in all kinds of directions that we couldn’t have anticipated in the

    The United States broke off diplomatic relations with Cuba in January
    1961, but every president since engaged in some form of talks with
    Havana, sometimes through secret channels or intermediaries, sometimes
    just over discrete issues. Jimmy Carter and Bill Clinton each made
    concerted efforts to transform the broken relationship only to be
    frustrated, leaving the two sides frozen in an ancient conflict long
    after the end of the Cold War.

    Mr. Obama came to office determined to succeed where his predecessors
    had not, convinced that the trade and commercial embargo had failed to
    undermine the Castro government while worsening Washington’s standing in
    Latin America. Campaigning for the White House in Miami in 2008, he told
    a Cuban-American group that he would meet with Mr. Castro “at a time and
    place of my choosing.”

    At his Chicago transition office after winning the 2008 election, the
    president-elect told Senator Richard J. Durbin, a fellow Illinois
    Democrat, that overhauling American policy on Cuba was a priority, but
    the circumstances would have to be right. “I thought it is long overdue,
    and it will take this president to step up and do it,” Mr. Durbin recalled.

    Once in office, Mr. Obama moved quickly, easing family travel and
    remittance restrictions, expanding cultural and academic exchanges, and
    resuming talks on migration, drug trafficking and postal services.

    But those discussions ended after December 2009 when the Cuban
    government arrested Mr. Gross, a contractor distributing cellphones,
    laptops and other communications equipment for the American government.

    The Cubans made clear that they would not release Mr. Gross unless the
    Obama administration freed the Cuban Five, a group of Cuban intelligence
    officers convicted in the United States in the late 1990s of
    infiltrating Miami-based Cuban-American dissident groups. Celebrated in
    Cuba as folk heroes, Los Cinco included Gerardo Hernández, who was
    serving two life terms for his role in the shooting down of two planes
    over Cuba in 1996 flown by an exile group dropping anti-Castro leaflets.

    Senator Patrick J. Leahy, Democrat of Vermont and a former prosecutor
    who had studied the cases of the Cuban Five and was convinced that their
    trials had been botched, lobbied the president and Eric H. Holder Jr.,
    then the attorney general, to consider trading the Cuban Five as
    leverage. But Mr. Leahy was told trading convicted spies for an unjustly
    detained contractor was unacceptable.

    “Our response was, ‘If that’s the case, then Alan Gross will die in
    Cuba,’ ” said Tim Rieser, a top Leahy aide.

    During a trip to Havana to visit Mr. Gross in prison, the senator and
    his wife, Marcelle, met with Adriana Pérez, the wife of Mr. Hernández,
    who clutched Ms. Leahy’s hands, tears in her eyes, and begged them to
    make it possible for her to become pregnant by her husband. Mr. Leahy
    won approval for Mr. Hernández to try artificial insemination, and Cuban
    officials transported his sperm to a fertility clinic in Panama.

    Change Begins

    “I didn’t ask for any quid pro quo, but I was asking for medical
    treatment and better accommodations for Alan Gross, and as they worked
    out the impregnation of this woman, suddenly his situation improved
    considerably,” Mr. Leahy said.

    Unknown to the senator, more significant change was in the works. In
    December 2012, just weeks after winning re-election, Mr. Obama directed
    advisers to determine whether he could do “something big on Cuba” during
    his second term. Mr. Rhodes and Mr. Zuniga, a Honduran-born Cuba expert,
    were charged with establishing a confidential channel with Havana.

    In April 2013, the pair sent a message, bypassing diplomatic channels to
    avoid leaks. The Cubans agreed to talk. Starting that June, the two
    White House aides began sneaking out of Washington and flying to Ottawa
    for secret talks with the Cubans in a Canadian government office.

    The Cubans came bearing gifts with a thinly veiled subtext: boxes of
    Cuban cigars and bottles of Havana Club rum that the Americans were
    barred by the embargo from bringing home and so had to leave in Ottawa.

    “Someone in Canada is very well stocked,” Mr. Rhodes noted ruefully.

    The Americans were obsessed with secrecy, inventing cover stories even
    for relatives to explain their out-of-town travels. When the Cubans
    suggested going out for dinner after their talks, the White House aides
    demurred, fearful of being spotted. Secretary of State John Kerry was
    informed about their talks, but few beneath him were. When Mr. Kerry
    held his own talks with Cuba’s foreign minister, Bruno Rodríguez,
    neither mentioned the secret channel, leaving the Americans unsure who
    knew what inside the Cuban government.

    Members of Congress, unaware of the secret talks, in the meantime met at
    the White House with Mr. Obama to press for action to free Mr. Gross.
    Mr. Durbin suggested appealing to Pope Francis for help. Mr. Leahy, who
    had met Cardinal Jaime Ortega, the archbishop of Havana, in Cuba, sent a
    letter asking him to raise the issue with the pope and another to
    Cardinal Sean Patrick O’Malley of Boston.

    By the time Mr. Obama met with Francis at the Vatican in March 2014, Mr.
    Gross and the Cuban Five were on both men’s agendas, as was a broader
    reconciliation between the two countries. Francis followed up with
    letters to Mr. Obama and Mr. Castro urging a resolution, hand-delivered
    by Cardinal Ortega, who was quietly whisked to the White House after an
    appearance at Georgetown University that had been hastily arranged as a
    cover story for his visit. As the cardinal met with Denis R. McDonough,
    the White House chief of staff, on his West Wing patio along with Mr.
    Rhodes and Mr. Zuniga, Mr. Obama dropped by to receive the letter.

    Around the same time, there was a breakthrough: Mr. Holder agreed to
    support commutation of the sentences of three members of the Cuban Five.
    (Two had already completed their sentences.) Mr. Obama gave Mr. Rhodes
    and Mr. Zuniga permission to negotiate their release as part of a deal.

    But the details were problematic. American officials did not want to
    appear to be trading three convicted spies for Mr. Gross, who they
    maintained had been unjustly imprisoned. They were helped when C.I.A.
    officials, hearing about the talks, mentioned that a Cuban man who had
    worked for them as a spy had been sitting in a Cuban cell for nearly 20
    years, and they wanted him freed. They could trade him for the Cubans
    while Mr. Gross would be released on humanitarian grounds.

    As details of the swap came together, the Obama administration announced
    the release of Army Sgt. Bowe Bergdahl in return for five Taliban
    prisoners, drawing protests from Republicans who blasted the move. Cuban
    officials believed the deal proved that Mr. Obama was open to prisoner
    swaps, and would therefore move swiftly to seal their pending agreement.

    In fact it did just the opposite. “The backlash to that was going to
    make it more difficult in some respects, and made it even more important
    that this be a bigger than just a spy swap,” Mr. Rhodes recalled.

    As spring turned to summer, Mr. Gross’s mental state deteriorated.
    Friends and family feared he would die in prison. He waged an eight-day
    hunger strike, halting only after his mother, Evelyn, called to beg him
    to eat. An effort to let him see his mother, who had cancer, failed. She
    died in June 2014.

    Mr. Gross, gaunt and hobbled by hip problems, vowed not to mark another
    birthday in Havana. He told friends that he fantasized about killing one
    of his Cuban captors and being killed in the process.

    Mr. Gross’s lawyer, Scott D. Gilbert, told the White House that if his
    client died, Mr. Obama would shoulder the blame. “We’re now at the point
    where we’re bringing my client out on the plank,” Mr. Gilbert told Mr.
    Zuniga during a tense meeting at the White House. “If you don’t deliver
    on this, Alan is going to die, and this whole thing will blow up in your

    Mr. Gilbert threatened to sue Mr. Obama on the eve of the 2014 midterm
    elections for failing to uphold the Hostage Act of 1868, which requires
    the president to take all action short of war to free an American
    captive held unjustly by a foreign government.

    Mr. Kerry sent a handwritten note of encouragement to Mr. Gross,
    followed by the president’s letter. Mr. Gilbert delivered them in
    separate trips to the military hospital in Havana where he was held. He
    also brought cryptic updates for Mr. Gross on efforts to win his
    release, typed into the body of routine legal memos to avoid detection.

    Restoring Relations

    By then, the talks had moved beyond Mr. Gross into details about
    restoring diplomatic relations and reopening embassies. In September,
    Mr. Rhodes and Mr. Zuniga arrived at the Vatican to present the entire
    package to senior advisers to the pope’s advisers.

    “At that point, you’re on the hook to the pope,” Mr. Rhodes recalled.
    “When we walked out of the Vatican, we knew this was over. That was the
    moment when I kind of exhaled.”

    Mr. Obama understood critics would accuse him of sacrificing human
    rights in Cuba for his own legacy. Just days before he would make the
    announcement, he invited Senator Robert Menendez, a Cuban-American
    Democrat from New Jersey, aboard Air Force One for an unrelated trip.
    Mr. Obama made no mention of the pending agreement, knowing Mr. Menendez
    would not approve.

    But the White House clued in supportive senators like Mr. Leahy and Jeff
    Flake, a Republican from Arizona, and sent them on an Air Force jet in
    December to collect Mr. Gross. Not long after taking off from Havana,
    the pilot announced they had entered American airspace. Mr. Gross stood
    up, thrust his arms in the air and let out a cheer. “I haven’t seen a
    happier man,” Mr. Flake recalled.

    Still, it was not over. After the dramatic announcement by Mr. Obama and
    Mr. Castro, the two sides settled into another six months of arduous
    talks to work out the details — and once again, the whole thing nearly

    Roberta S. Jacobson, the assistant secretary of state for the region,
    led talks with Josefina Vidal, her Cuban counterpart, that were
    complicated by decades of grievances like financial claims and fugitives
    harbored by Cuba. The two sides decided to stick to matters related to
    opening functioning embassies.

    For the Cubans, that meant finding a bank to handle their transactions.
    The Americans “talked to every bank we could think of,” a senior State
    Department official said, requesting anonymity to describe private
    talks, but none would risk it. Finally, a small bank in Florida whose
    owners supported the new policy volunteered.

    But Cuba refused to allow American diplomats to travel without
    permission, a nonstarter for the Americans. By March, the Americans
    worried the talks might fall apart. Tensions rose in April at the Summit
    of the Americas in Panama, where Mr. Castro delivered a speech whose
    anti-American rhetoric was “a little jarring” to some of the Americans,
    the State Department official said. A long, late-night meeting between
    Mr. Kerry and Mr. Rodríguez left the Americans again fearing collapse.

    Two weeks went by without word from the Cubans. At the State Department
    and the White House, officials were “buzzing around, getting uptight,”
    the State Department official said.

    But then the Cubans finally agreed to allow travel without permission as
    long as they were notified. Not ideal, but the Americans accepted. The
    deal was done.

    As Mr. Obama anticipated, critics object. “This is the embodiment of a
    wrongheaded policy that rewards the Castro regime’s brutality at the
    expense of the Cuban people’s right to freedom of expression and
    independence,” Mr. Menendez said in a speech prepared for delivery on

    Nonetheless, on Friday morning, around dawn, Mr. Kerry will board an Air
    Force plane for Havana. Dissidents will not be at the embassy
    flag-raising ceremony, but he will meet with them separately. It will be
    the first visit by an American secretary of state in 70 years.

    A version of this article appears in print on August 14, 2015,

    Source: A Secretive Path to Raising U.S. Flag in Cuba – The New York
    Times –