New York — When Allen Weisselberg’s son got married in 2004, Donald Trump offered the young couple a generous wedding gift: use of an apartment, overlooking Central Park, rent-free.

Market rent on the apartment, owned by the Trump Organization, would have totalled hundreds of thousands of dollars over the seven years the couple wound up living there. The move — carrying tax implications as well as benefits — in some ways brought the family nearer to the living arrangements of Trump’s own children. The unusual deal is one of several that benefited the family of Weisselberg, Trump’s right-hand man on all matters financial...

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