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(CNN) —  

President Donald Trump has had at least 10 encounters with Lev Parnas and Igor Fruman, the indicted associates of Rudy Giuliani the President has adamantly claimed not to know.

Prosecutors allege Parnas and his business partner Fruman illegally funded Republican politicians and campaigns with money from foreign nationals in attempts to buy influence. That pair are also said to have aided Giuliani, the President’s personal attorney, in efforts to investigate former Vice President Joe Biden related to Ukraine.

Since their indictment, Trump has stated publicly that he doesn’t know Parnas and Fruman.

The interactions, of which many new details are being reported here for the first time, include VIP photos at campaign events, attendance at high-dollar fundraisers and a retreat. They also include a pre-inauguration gala for high-dollar donors, an intimate dinner with the President and photos at the White House Hanukkah dinner with the President, Vice President and Giuliani.

On seven of the occasions, Trump posed for photos with either Fruman or Parnas.

The details raise new questions about Parnas and Fruman, including how Parnas gained VIP access to inaugural events and how Fruman was able to take a picture with Trump before a 2016 event with no record of donating to the campaign.

Lawyers for both men either did not respond to CNN’s requests or declined to comment. Additionally, both the White House and the Trump campaign did not comment. Rudy Giuliani did not answer questions about his connections to the pair.

“I don’t know them,” Trump added. “I don’t know about them. I don’t know what they do but I don’t know, maybe they were clients of Rudy. You’d have to ask Rudy, I just don’t know.”

But a CNN KFile review of photos on social media – including of Parnas’ since removed Facebook, photos on his Instagram reported in October by the Wall Street Journal, and other photos and videos splashed across the Internet – paint a far more casual and familiar relationship than the President has let on.

Parnas and Fruman were arrested in October while they were attempting to leave the country. They were indicted on four counts, including conspiracy to violate the ban on foreign donations to federal and state elections, making false statements and falsifying records to the Federal Election Commission. They pleaded not guilty in Manhattan federal court last month to the charges. Parnas and Fruman were ordered to house confinement and were subject to GPS monitoring after they each secured a $1 million bond.

Two other associates of Parnas and Fruman, David Correia and Andrey Kukushkin, also were indicted on a conspiracy charge. Correia and Kukushkin also have pleaded not guilty.

Here’s a full list of the interactions:

When: March 7, 2014

Where: Golf tournament at Trump National Doral, Miami, Florida

Who attended: Lev Parnas, Jared Kushner, Ivanka Trump, Donald Trump, Eric Trump, Donald Trump Jr.

Photos posted on social media and Getty Images, first reported by CNN and Politico, show Parnas met Trump at a fashion show hosted by Ivanka Trump for the luxury brand Carolina Herrera during a golf tournament. The event also was attended by Trump’s sons Eric and Donald Jr. and Ivanka’s husband Jared Kushner, who is now a senior White House adviser. A White House spokesperson for Jared and Ivanka declined to comment on the event last month to CNN.

When: Oct. 23, 2015

Where: Trump campaign rally at Trump National Doral Miami, Florida

Who attended: Parnas, Trump

Photos from Parnas’ Instagram show he attended a rally held by Trump at Trump National Doral in Miami. The pictures show Parnas and his son posing with candidate Trump outside of the ballroom where Trump held his rally. Pictures show the pair had passes for the event. Parnas did not return a request for comment and his attorneys declined comment.

When: October 2016

Where: Fundraiser in the home of Robert Pereira in Hillsboro Beach, Florida

Who attended: Parnas, David Correia, Rudy Giuliani, Trump

In October 2016, Parnas and David Correia attended a fundraiser for Trump at the home of businessman Robert Pereira in Hillsboro Beach, Florida. CNN’s KFile matched photos from Parnas’ Instagram and Correia’s Facebook to a fundraiser held in the home of top Trump donor Robert Pereira. The photos from Parnas and Correia’s social media show them posing with Trump inside Pereira’s home. The Wall Street Journal reported that Rudy Giuliani also attended the event. Parnas and Correia’s wife Katie made a $2,700 donation to Trump’s campaign in October 2016.

Correia nor his attorney returned a request for comment. The Trump campaign did not respond to a request for comment. Giuliani did not answer questions about the event.

When: Dec. 16, 2016

Where: Orlando, Florida, Trump “Thank You Tour Rally”

Who attended: Trump, Igor Fruman and Florida campaign workers and VIPs

A photo posted in an interview with Igor Fruman in the outlet Forum Daily shows him posing with Trump on the day of the “Thank You Tour Rally” in Orlando, Florida. The photo has been misreported as having been at Mar-a-Lago in 2018. CNN’s KFile identified the photo as being from the rally by cross referencing the picture with other public photos posted on social media by attendees at the event and by speaking to an attendee who confirmed the date and location. Vice President-elect Mike Pence and Rick Scott, then Florida’s governor and now a US senator, also attended the photo op before the event.

It is unclear how Fruman, who had not yet donated to the Trump campaign nor his PACs or had any reported record of volunteering for the campaign, attended the event. A lawyer for Fruman declined to comment.

When: Jan. 19, 2017

Where: Pre-inauguration gala at Union Station, Washington, DC

Who attended: Parnas, Trump and hundreds of VIPs including the first family and future White House officials

Parnas stood several feet from Trump at a pre-inauguration gala, according to a series of photos posted on Facebook by donor and radio host John Catsimatidis. Parnas’ attendance at the gala was first noted by Politico and was identified by CNN’s KFile as the Candlelight Dinner at Union Station. Parnas appears in a group of people standing in the crowded gala near Trump as he speaks to guests. In the photos, Trump can be seen talking to Patriots owner Robert Kraft as Parnas stands near Catsimatidis.

A photo posted on Facebook by Parnas’ son Aaron Parnas at a gala that week also shows him posing with Betsy Devos, soon-to-be Education Secretary, at what appears to be a ball on inauguration night. Aaron can also be seen in the ticketed seating area at the inauguration in a CNN photograph.

It is unclear how Parnas attended the Candlelight dinner, tickets of which were given to donors of $250,000 or more to the president-elect’s inaugural committee.

Catsimatidis did not respond to a CNN comment request asking if recalled if he met the President. Parnas’ attorney did not respond to questions asking if he met the President.

When: March 3, 2018

Where: Mar-a-Lago resort in Palm Beach, Florida

Who attended: Trump, Fruman

Photos provided by Fruman to several Russian language news websites in 2018 and 2019 show he attended a March 3, 2018 Trump-Pence Victory Reception at Mar-a-Lago. Fruman’s photos match other attendees from the event.

Fruman made a $2,700 donation to the victory fund a little over a week earlier. Fruman reportedly told the outlet Forum Daily he took part in a meeting where Trump met with donors.

Fruman did not return a request for comment. His attorney declined to comment about the event.

When: April 30, 2018

Where: America First Action dinner at the Trump International Hotel, Washington, DC

Who attended: Trump, Parnas, Fruman, Roy Bailey and other donors

Photos show Parnas and Fruman posing with Trump at a private dinner hosted by America First Action SuperPAC weeks before the pair’s company Global Energy Producers donated $325,000 to the super PAC. The venue was previously widely-misreported as the White House, based on Parnas tagging it as such on Facebook. CNN’s KFile identified the venue as the Trump Townhouse in the Trump International Hotel through previously posted photos of the venue. The suite boasts an exclusive entrance and a dining room table that fits 16 people and Fruman reportedly told a Russian-language outlet he attended a meeting with Trump and only eight people around the same time.

Trump has previously attended America First dinners and the super PAC has used the Trump appearances at the dinners to court prospective donors.

Kelly Sadler, a spokeswoman for the super PAC, told CNN’s KFile in an email, “As has been widely reported, Lev Parnas and Igor Fruman attended America First Action events, including a dinner in April and a leadership summit.”

When: June 18-19, 2018

Where: America First Action summit at Trump International Hotel, Washington, DC

Who attended: Trump, Trump Jr., Parnas, Fruman, Correia,

At America First Action’s two-day leadership summit in June 2018, Parnas appeared in photos standing next to Trump and near Trump Jr. The photos were posted on Instagram. In another photo, Trump can be seen posing with Correia and Fruman.

When: Oct. 20, 2018

Where: Midterm rally in Elko, Nevada

Who attended: Trump, Parnas, Fruman, Andrey Kukushkin