Klinsmann moved to Arsene Wenger's Monaco in 1992, the German striker's first season seeing them catapult to a second-place finish in Ligue 1.
He also played a pivotal role in helping his side to reach the semi-finals of the Champions League, where they lost to eventual winners AC Milan in the 1993/94 season.
Klinsmann joined the club on the basis he would spearhead the attack alongside Weah, who went on to win the Ballon d'Or in 1995.
But little did he know, the Monaco star would sign for rivals and French champions Paris Saint-Germain the day after he put pen-to-paper on the deal.
Wenger knew he would not be able to secure his man if he had known Weah was going to leave for the French capital.
Speaking exclusively to talkSPORT for My Sporting Life - to be aired at 8pm on Sunday - Klinsmann revealed how his move to France came about and the shock curveball that came shortly after signing.
"I went to the president, the owner of Inter Milan, and asked him politely if it was okay I moved on and I promised him I wasn't going to go to another Italian team", Klinsmann said.
"He said it was no problem and that he'd check it out. Then suddenly AS Monaco knocked at the door and Arsene Wenger was the manager in those days.
"So, we took the helicopter from Milan to Monaco and went there, we had negotiations and it was all very easy. I had the offer to play up front with George Weah, who was one of the top strikers.
"Arsene said 'yeah I want you two playing up front' and I thought 'wow this is like winning the lottery playing with George Weah up front'.
"So, I signed the contract and I go the next day to Monaco and George Weah gets sold to Paris Saint-Germain.
"I went right away to Arsene and said 'Arsene, you promise me I can play up front with George Weah, and he said 'Well if I told you we were selling him you wouldn't have signed the contract'.
"I said 'Yeah that's right, I wouldn't have signed the contract.' But the deal was signed, and I spent two years with Wenger in Monaco."
Despite this early setback, Klinsmann revealed he enjoyed his time in the south of France.
"French football, especially on the technical side, is very good football," he added. "Good teams, very competitive, also very physical.
"I got some real experiences there with some defenders but I had some amazing times. With Arsene Wenger I had not only an amazing manager but also a philosopher of life, a person that looks far beyond the football pitch.
"I learnt a lot from him in those two years and then I wanted to move on.
"The games at home were seen by maybe 5-6,000 people and the only games that sold out were against Paris Saint-Germain or Olympique Marseille, those were the two main ones.
"Same with the Champions League. But after two years, I felt there was more to it, I've got to move on.
"I went to Arsene and I said it's time for me to go. I had another year on my contract so he said 'well if you get me a club that will spend a little bit of money for you I'll let you go'. I was already thirty by then."
Tottenham were that club who gave Klinsmann that lifeline, the £2million sale sanctioned by Wenger, who would go onto become a nemesis of the club when in charge of Arsenal.
talkSPORT is to air a new series of My Sporting Life, speaking to leading athletes across the world about their life in sport. Listen to the opening episode on Sunday at 8pm, with former Bayern Munich, Tottenham and Germany striker Jurgen Klinsmann in discussion with Paul Coyte.