"The hard part is that Chelsea and Ivanka were friends."
Politico said the pair have opted not to be seen together since long before Ted Cruz threw in the towel on the race making Trump the presumptive Republican nominees.
The polarising billionaire has already slammed Clinton for playing the "women's card" and said she got "schlonged" by Obama in 2008, in what is expected to be just a taste of the sledging to come once the race begins in earnest.
Despite the political differences of their parents Chelsea and Ivanka share a number of similarities and have spoken warmly of each other in the past.
Chelsea told Vogue Ivanka reminded her of her famously charismatic father Bill, for a profile the magazine ran on Trump's daughter.
"She's always aware of everyone around her and ensuring that everyone is enjoying the moment," she said.
"It's an awareness that in some ways reminds me of my dad, and his ability to increase the joy of the room.
"There's nothing skin-deep about Ivanka. And I think that's a real tribute to her because certainly anyone as gorgeous as she is could have probably gone quite far being skin-deep."
One associate of the pair who wanted to remain anonymous has previously said they "genuinely relate" to one another and tend to run in the same New York circles.
Both have grown up in high-profile families that have endured sex scandals in the public eye. They have since both become parents and devoted themselves to their family's work - Chelsea, 36, at the Clinton Foundation and Ivanka, 34, at the Trump organisation.