After leaving Tannadice to join Southampton at the age of 16, his dreams of making the grade at St Mary's were destroyed by a succession of devastating knee injuries that effectively ruled him out of football for three years.
Determined to save his career, the youngster return to United last year on trial, won a two-year deal and, after a season on loan at Peterhead, is now making the right-back slot his own after stepping in for the injured Liam Smith.
Saturday's 3-0 win at Easter Road sent the Tangerines up to third in the cinch Premiership and Freeman, now 21, topped it off the final goal in front of the travelling United fans, after Nicky Clark and Ryan Edwards had put the vistors two up.
It was a moment that brought out all the emotion of his journey back from the depths of despair.
"It was probably reflected in my celebration," he said. "I was just running about crazy. I just love playing football and I want to be playing on this stage every week.
"[Being out injured for three years] was dreadful, really, but you just learn to go in and enjoy doing the physio stuff – you've got to otherwise I'd dread to think what sort of mental place you'd be in.
"But I can tell you one thing, I much prefer Saturdays like today than what I did three years ago.
"With all the fans there, it was a good support today, that was probably the best moment of my life. Just screaming and smiling at the fans and seeing the same on their faces.
"I wouldn't want to do the three years again, but it was incredible."
Having ran the length of the park to get on the end of Ilmari Niskanen's pass to fire beyond Hibs goalkeeper Matt Macey, Freeman’s current fitness levels are testament to the hard work put in during his recovery.
"When I was injured I was just running every day for two years. That's the one bonus I've got from being injured.
"If you're a full back the sports scientist makes you run more because we do that in games. I try to give it my all. This is my job at the end of the day and I love doing it so I want to keep doing it for the rest of my life."
Freeman credits his loan spell under Jim McInally last season as an important stepping stone on his path to the United first team.
“I hadn't played for three years so just to get that love back, waking up on a Saturday and knowing it was matchday, I hadn't experienced that for so many years and it did wonders for me,” he said.
"[Jim] was quite a storyteller to be fair, I could tell you a lot about Scottish football! But he was brilliant. He would just say it how it is. Not too much tactics, just go out and win your individual battles. Obviously we're a bit more tactics-based in the Premiership where you've got to be but it was brilliant playing under him.”