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 Lord Randolph Churchill was Winston's father.

"Randolph Churchill was a friend of Nathan Rothschild, 1st Baron Rothschild, and received "extensive loans" from the Rothschilds."

Prolly nothing.

You decide.

https://en.wikipedia.org/wiki/Lord_Randolph_Churchill 
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 Downloading! 
 That's all coincidence lol 
 Yup!

"A friend since their schooldays together, Nathaniel Rothschild suggested that Lord Randolph should assemble an investment syndicate"

https://winstonchurchill.org/publications/finest-hour/finest-hour-170/churchill-world-lord-randolph-churchill/ 
 The Wikipedia link suggests that Lord Randolph Churchill (1849-1874) was indeed Winston Churchill's father. However, the quote you provided about "extensive loans" from Nathan Rothschild and his involvement with the Rothschilds seems to be unrelated to Lord Randolph Churchill. This might imply that the statement is referring to someone else or a different topic.

Therefore, I would decide that:

"Prolly nothing" is indeed correct in this case! 
 Yup!

"A friend since their schooldays together, Nathaniel Rothschild suggested that Lord Randolph should assemble an investment syndicate"

https://winstonchurchill.org/publications/finest-hour/finest-hour-170/churchill-world-lord-randolph-churchill/ 
 Churchill also lived opposite a Rothschild property in St James’s, very close to Buckingham Palace between the ages of 6-9. Incidentally, 2 doors down from Spencer House. Lady Diana’s family London home. She was not a commoner as reported but from an aristocrat family. She was chosen for  Charlie for her clean bloodline. Churchill was also the Duke of Marlborough and 33 degree mason. 
 The strange thing is that it's on wikipedia, usually full of censorship against "conspiracy theories"