Crowe was beginning to reach the peak of his batting prowess in the mid-1980s when Gillespie played alongside him in Australia during the Benson & Hedges Series against the likes of Australia, India and Sri Lanka.
His brilliant scores of 188 against the West Indies and then Australia in the 1985 test match where Sir Richard Hadlee took 15 wickets had already set him apart from his peers.
From his 17 test centuries, it was those efforts and the extraordinary 299 against Sri Lanka in 1991 at the Basin Reserve which are the most remembered, along with Crowe's brilliant batting and shrewd captaincy tactics during the 1992 Cricket World Cup.
Remembering his early days, Gillespie has seen the comments made elsewhere that Crowe was New Zealand's greatest ever batsman.
While he would contend there was a select handful capable of having a similar influence on a match, it was the purity of Crowe's technique - standing tall at the crease and using the feet to great effect - which made him stand out.
"He was one of them [who was great], there were other guys who were as effective," said Gillespie.
"But when he was in his prime, he was one of the most classical you ever saw, and that's what people will remember."
While the stats tell the story - 5444 test runs at an average of 45.36 in a career that could have had another couple of years if not for chronic knee problems - Gillespie was pleased to see it was also Crowe the man who seemed to grow in recent years.
Admitting in his biography that he was often wracked with self-doubt, Crowe said he became someone who harboured grudges, with "a disconnected spirit and soul overwhelmed by the ego ... "
It often led to tense relationships with media, cricket officials and team mates.
"It was part of his career where he was almost his own worst enemy," said Gillespie.
However, since that time and especially after the diagnosis of his condition in 2012, Crowe settled into the statesman role, often keeping track of his former playing colleagues, mentoring current New Zealand batsman and writing extensively about the sport in well regarded articles.
Gillespie said he had the chance to meet up with Crowe about nine to 10 months ago and his former team mate spoke very enthusiastically about Gillespie's son on the professional golfing circuit.
"He knew everything about Nick and said I'd be remembered for everything to do with being the father of Nick Gillespie the golfer."
This renewed outlook and due respect received from the public culminated in the warm reception and then standing ovation Crowe received during the 2015 World Cup pool match at Eden Park, where he received his entry into the ICC Hall of Fame. "It was a special occasion for him and he became a better person as a result of having to think about things."
However, Crowe was unable to join Gillespie and others from the 1985-86 New Zealand team for their reunion at the Basin Reserve a few weeks ago, a sure sign that time was running out.
Gillespie said a lasting legacy will be the support Crowe gave the likes of Black Caps Ross Taylor, Martin Guptill and Kane Williamson in their development as world class batsmen.
"They're starting to say it now and you can see he has had an influence on them."
He has also had a chance to reconnect with many former players on social media who have posted their thoughts in the last two days, many shocked to have lost the great player. "They didn't expect him to go."
Gillespie will travel to Auckland to attend Crowe's funeral at Auckland's Holy Trinity Cathedral next Friday.
Holy Trinity Cathedral dean, the Very Reverend Jo Kelly-Moore, said the funeral would be a time to give thanks for Crowe's life. "The funeral is a time for those who loved Martin and those he loved, as well as for friends, and for the sports community."