But he is confident McGregor can be the latest in a long line of great centre- backs for Glasgow Rangers if his move to the Ibrox club goes through.
Lennon was not at all surprised to hear that Gers gaffer Ally McCoist is interested in adding the defender to his squad this summer.
The former St Mirren boss revealed the Glasgow giants were keen on him back in 2010 after he first went full-time and joined the Paisley club.
And he has no doubt at all that the 28-year-old will be hugely successful if he joins the SPFL Championship club in the coming weeks.
He said: "I always knew there was a bit of interest there from Rangers, that they liked him. Even before he did his two cruciate ligaments. I hope it all works out.
"I take a lot of pride in how well Darren has done and the level that he has reached.
"He was at Cowdenbeath before I was appointed manager. But he was let go.
"I went along to watch him play in a game for Junior club Arniston Rangers and got the club to pay a £1,500 fee - which was a lot of money for us - to sign him. It was money well spent.
"When he came to St Mirren his attitude, desire and hunger to succeed meant he won the fans over quickly. He won Player of the Year from the majority of the supporters' clubs in his first season.
"Yes, he has had serious injury problems as well. But the fact he has come back as good as ever from them just shows you the strength of character that he has.
"I have no doubt he will succeed if he moves to Rangers."
Rangers have had a long line of outstanding centre- backs in modern times - including Jean Alain Boumsong, Madjid Bougherra, Carlos Cuellar and Davie Weir.
And the Light Blue faithful have high expectations of those who are chosen to play in the heart of the rearguard - even given their current off-field difficulties.
BUT Lennon, who led the Buddies to an historic League Cup triumph two seasons ago, feels McGregor would not disappoint any Gers supporter.
He remarked: "Darren always works on his game. He has an influence in both boxes. He is very physical and has great aerial ability.
"He knows where his strengths are. But he works at all areas of his game.
"He works at his distribution and has improved immensely in that department.
"He is a good defender. He reads the game well and is quick off the mark. His pace gets both himself and his team out of a lot of trouble.
"On top of all that, he is a really humble guy. After his first season at St Mirren he had to make an acceptance speech after getting presented with the Player of the Year award. He broke down it meant so much to him.
"I am delighted for him that he has been linked with a club like Rangers. I hope it comes off for him.
"If it does it will show any young player that suffering a setback - as Darren did when he was let go by Cowdenbeath - that it doesn't mean things are over for you. Darren has turned his career around.
"I believe that if Darren hadn't been so unlucky with injury then he would have left St Mirren for a bigger club long before now.
"It is no surprise that Ally recognises his qualities and wants him for Rangers."
Before joining St Mirren as manager four years ago, Lennon served his apprenticeship as a boss in the lower reaches of Scottish football with Cowdenbeath.
The 45-year-old steered the Fife club to two consecutive promotions - just as McCoist has done in the last couple of seasons.
BUT he knows just how difficult it will be for Rangers to compete in the second tier and complete the final stage of "The Journey" during the 2014/15 campaign.
Especially with Edinburgh clubs Hearts and Hibs both alongside them pushing to win automatic promotion back into the top flight.
However, he feels McGregor, whose contract with St Mirren has expired, will relish the challenge if he completes his free transfer in the days ahead.
Lennon said: "The Championship will be a fantastic league next season with Hearts, Hibs and Rangers all in it.
"But I am sure Darren will step up to the plate and do what is required if he completes this move.
"Everybody is saying that it is going to be a three-horse race. But they should not forget that other clubs in that division are more than capable of getting results.
"They say that the Championship is the most competitive league in the country, the most difficult division to get out of.
"I would agree with that. That will be especially true next season.
"But Ally knows exactly what will be required - and that is why he is interested in getting Darren in to be a part of the set-up at Rangers."