Barcelona initially wanted someone with links to the club to become Sir Bobby's assistant, but he insisted it be Mourinho.
Not in vain.
Sir Bobby entered a divided club following the departure of legendary coach Johan Cruyff and needed someone he trusted implicitly who could help deliver his message in another foreign language.
By this point, Mourinho's role had long since changed.
He helped out on the training ground. He produced intelligence dossiers on the opposition that Sir Bobby described as the best he had ever seen. Most importantly, he is used to dealing with international players.
As midfielder Guillermo Amor explained, in the testing environment the pair again complemented each other.
“They managed to create a good atmosphere and a very strong team,” he said.
“Jose communicated more with the players thanks to his fluency in the language and his age, which was very similar to ours.
“He had a lot of respect for Bobby and Bobby had a lot of faith in everything Jose could do on the field and in the dressing room.”
Sir Bobby won the Cup Winners' Cup, Copa del Rey and Copa del Rey in what turned out to be his final season with Mourinho before the Barcelona manager was promoted to general manager and replaced by Louis van Gaal.
Mourinho told Sir Bobby he wanted to leave out of loyalty, but his mentor convinced him to stay, having already informed Van Gaal of the benefits of keeping his assistant.
Had Mourinho not spent another three years at Camp Nou under Van Gaal, the Portuguese might well have followed Sir Bobby to Newcastle in 1999.
Instead he acted alone, but Sir Bobby's influence lives on.
To this day, Mourinho treasures the moments the couple's families shared in Sitges, the food Sir Bobby never allowed him to pay for and the life lessons it taught him.
That is why the 62-year-old man considers himself a “little magpie.”
“The club there knows how much I love and respect them,” he told CBS earlier this month. “I learned this love from Mr. Robson.”