The Rangers winger has left Ibrox for the season to play at Easter Road.
The winger had the option making the switch to Dutch second-tier side NAC Breda but has decided to test himself in the Scottish Premiership.
The paper say that initial conversations had taken place between his agents and clubs, before the personal touch from Heckingbottom convinced the teenager his future was best served at Easter Road.
As quoted by The Herald, Middleton said: "The way the manager [Heckingbottom] spoke to me on the phone was what swung it for me.
"I heard the things he had to say about the club and I was pretty much set in my mind after that phone call that I’d really like to come to Hibs.
"When you get the opportunity to play for this sort of club in this stature of league, you can’t really turn that chance down."
A good move for Middleton?
It's certainly a big opportunity for the 19-year-old.
It became clear in the second half of last season that the winger would not be getting opportunities in Steven Gerrard's first-team, despite initially being selected with regularity.
Now he has the chance to prove to Gerrard that he his worthy of inclusion.
If he performs well in the Scottish Premiership and becomes a stand-out at Hibs, it will greatly aid his ambitions of making it at Ibrox.
That will only be a benefit to Rangers too clearly. Fans and staff at the club will have a great opportunity to see the player's development up close.
The loan market is being utilised as a development path for Rangers' big talents with Greg Docherty and Ross McCrorie also sent out on loan over the last 12 months.
Can Middleton make his mark and return to Glasgow ready to stake a claim?
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