In the wake of the Orlando massacre of 49 people, Trump cited Clinton Foundation's acceptance of up to $25 million in contributions from Saudi Arabia's government as a sign she is not dedicated to the cause of LGBT Americans. Other Middle Eastern donors to the foundation include Oman, Kuwait, Qatar and the United Arab Emirates.
"She's no friend of women and she's no friend of LGBT Americans. No friend. Believe me," he said Tuesday in Greensboro, North Carolina, while repeating his push for a ban on Muslims traveling into the United States.
"How can you be a friend when you take many, many millions, tens of millions of dollars, $25 million from one country they think?" Trump said. "How can you be a friend when these countries are oppressive to LGBT, when they're oppressive to everybody? How can you be a friend?"
What Trump hasn't mentioned on the campaign trail: He, too, has financial ties to some of the same countries. From licensing his name to a golf club in Dubai to leasing his suburban New York estate to former Libyan strongman Moammar Gaddafi, Trump has launched several new business ventures connected to Middle Eastern countries since 2000.
Those ties could complicate Trump's effort to undercut Clinton's support with the LGBT community and women by linking her to Middle Eastern countries that have contributed to the Clinton Foundation.
Trump insisted his business ties shouldn't be compared to the Clinton Foundation's acceptance of foreign donations.
"It's much different when she is selling our country down the tubes with her bad judgment and corrupt thought process," he told CNN in a statement. "I am an international businessman with worldwide relationships and tremendous success and I'm going to do for the country what I did for my business."
Clinton's campaign would not comment on the comparison of Trump's business ties and the donations to the former secretary of state's family foundation.
The human rights abuses of the countries over which Trump has attacked Clinton have been widely reported. In Saudi Arabia, homosexuality can be punished by death.
But Trump has business ties to many of those countries as well.
He made his first real estate venture into the Middle East in 2005, when he licensed his name to United Arab Emirates developer Nahkeel LLC, controlled by Dubai's crown prince, Sheik Mohammed Bin Rashid Al Maktoum for a massive $400 million hotel project. He was accused in 2006 of enslaving tens of thousands of boys to use as camel jockeys over three decades.
"I am delighted to invest, manage and sell this project on what is clearly the best location in Dubai," Trump said in a statement
when the project was announced.
His deal with the developer also gave it the right to use the Trump brand in 19 Middle Eastern countries.
The hotel was never constructed -- Nakheel suspended work in 2008 and instead built a park there.
Trump also licensed his name to a golf course project in Dubai -- though his name had been removed from public signage late last year
amid controversy over his comments critical of Muslims.
In 2012, Trump signed a licensing deal worth $2.5 million, plus another $323,000 in management fees with Garant Holding over a hotel in Azerbaijan, along the Caspian Sea, according to his personal financial disclosure. It would be, he promised in a 2014 news release, "among the finest in the world."
Garant's chairman is Anar Mammadov, a 35-year-old billionaire whose family is part of the country's leadership. The country was identified as the worst place to be gay in Europe by the ILGA-Europe Rainbow Index
, which cited frequent hate crimes.
Already a presidential candidate in August 2015, Trump incorporated eight companies that used the word "Jeddah" -- Saudi Arabia's largest city -- in their titles, his personal financial disclosures reveal. Four of those companies were disbanded two months later.
that they were likely connected to a hotel development there, pointing out that the names for the companies are almost identical to those he used in Azerbaijan.
He also has business ties to Indonesia -- where gay sex is punishable by public caning, a fine of $37,400 and more than eight years of prison time.
Trump Hotels Collection last year partnered with PT Media Nusantara Citra to manage a new hotel and resort development in Bali.
Trump's son, Donald Trump Jr., touted that development in a statement at the time, saying the company seeks "only the most valuable destinations," The Jakarta Post reported
Trump has also dealt with Middle Eastern countries, including Saudi Arabia and Libya, within the United States.
In 2001, he sold units in his Trump World Tower in New York City to Saudi Arabia's government.
In discussing the United States' military relationship with Saudi Arabia at a May 19 fundraiser for New Jersey Gov. Chris Christie, Trump bragged about apartment deals with Saudi Arabians.
"I have so many friends there, Saudis, they buy my apartments, you wouldn't believe it, OK?" Trump said, to laughter from the crowd. "Now look, they're great, they're all great," he said.
Another notable example: Trump's deal with Gaddafi in 2009, two years before Gaddafi's death.
Set to address the United Nations General Assembly in New York for the first time, Gaddafi was seeking a property to pitch a large tent. Turned away by New York City and New Jersey officials, Libya sought Trump's Seven Springs estate in Bedford.
Trump recalled that deal, bragging about it in an interview with CBS' "Face the Nation"
"I made a lot of money with Gaddafi, if you remember," Trump said. "He came to the country and he had to make a deal with me because he needed a place to stay."
Local Bedford officials shut down the rental, stopping work on the tent and citing the lack of a permit to build one.
"He paid me a fortune, never got to stay there, and it became sort of a big joke," Trump said of Gaddafi.
that Libya's representatives paid Trump $150,000 for the rental.
Still, Trump has kept up the attacks on Clinton, calling on the former secretary of state to return her family foundation's donations from Middle Eastern countries.
He lambasted Clinton for her family foundation's acceptance of donations from Saudi Arabia's government again Wednesday in Atlanta, and then Thursday night at a fundraiser in Dallas.
"They enslave women. As far as gays are concerned, OK, think of it -- they throw gays off buildings. They kill them. Countries that contribute to her foundation," Trump said. "And she should give all that money back to all these countries."
He added: "And you know what? LGBT is starting to like Donald Trump very much. Starting to like Donald Trump very, very much, lately."
His business ties haven't stopped the RNC from backing Trump's attack on the Clinton Foundation over its acceptance of foreign donations.
"When you're the top diplomat of the United States and foreign governments with appalling human rights records are donating millions of dollars to your family foundation," RNC spokesman Michael Short said, "that's an unprecedented conflict of interest and entirely different than opening up a hotel or golf course."