Gullit was first convinced to join Chelsea in 1995 by Glenn Hoddle before he eventually took charge as manager a year later.
In that first season as manager, Gullit led Chelsea to their 1996 FA Cup triumph.
Asked whether he had doubts about joining the Blues at the time, Gullit told Tribalfootball.com: "No, you can't say ‘if’. The thing is, it happened. I'm happy.
"It was a surprise for a lot of people that I went to Chelsea anyway. Something changed at Chelsea when we played there. Something changed there, I felt it. I remember when I was coach the first couple of games when we kept the ball and the fans were a little bit like “get that ball in the box”, it took them a month, two months to adjust a little bit to the football we tried to play and eventually they loved it.
"I think Glen Hoddle started it by getting me there and getting Mark Hughes there. So therefore it was a turning point for Chelsea when we arrived there and look what happened, Chelsea is now the elite of Europe with two champions leagues. Unbelievable, fantastic."
Don't judge too soon
Reflecting on how Chelsea is now run by the club's current owners, Gullit insists it's still too early to judge.
Having seen another managerial change, with Enzo Maresca removed on New Year's Day and replaced by Liam Rosenior, Gullit continued: "I know Chelsea well. Managers there don’t last long, even when they’re successful. The real question is: are these players bought by the coach or by the club?
"Does the coach have to deal with what he gets rather than what he wants? It feels like recruitment is driven more by the owners than the coach. Is that the right way? I don’t know yet. Is it sustainable? Can you win trophies like that? Time will tell.
"Chelsea are hard to read. Every season feels like a work in progress, but they’ve been at this for two or three years now. I want to know: what’s the end game? What’s their philosophy? They need more experience - players who read the game."
Chelsea option right for Hato
At Chelsea, Gullit is watching fellow Dutchman Jorell Hato closely. While admitting he had concerns when Hato left Ajax for Chelsea last year, Gullit is becoming convinced it was the right decision.
He explains, "I had doubts about his transfer to Chelsea. He was one of the best young players in Holland, and sometimes it’s better to stay longer and gain experience. He was captain at Ajax at such a young age, but Ajax were struggling. He escaped a difficult situation at Ajax. He saw it coming and thought it was the right time to leave. I don’t know if Chelsea is the right club for his development.
"He hasn’t played many games since the move, now he isn't being selected regularly for the national team anymore and with the World Cup coming, that’s difficult. If he plays more at Chelsea he can get his place back in the national team. I understand why he left, it imploded a little bit. Ajax losing 6-0 in the cup last night shows how much turmoil there is there, so I can understand why he left.
"Whether Chelsea is the right club at this stage, given they’re also in transition, only time will tell. I said the same thing about Nathan Ake when he went to Manchester City. But if Hato plays regularly under Rosenior, he can reclaim his national team place."
- Ruud Gullit was speaking to Tribalfootball on behalf of Foot Italia