Sherwood was a teammate of Campbell at the time at Tottenham, himself playing for the club between 1999 and 2003.
Campbell quit Spurs on a free thanks to the Bosman ruling in 2001, for rivals Arsenal, which led to personal success for him, but also saw him become a hate figure for his former fans who branded him a 'Judas'.
Sherwood says that Spurs players did not hold any grudges against the centre-back, and from his own perspective he held the club responsible, for letting the England international's contract run down in the first place.
He told The Independent: "Sol had not been offered the deal he wanted early enough in his contract negotiations and gradually time ran out for Spurs without them taking the initiative. By the time they made an offer, his mind was made up to go.
"It caused outrage among the Tottenham fans but in the dressing room it was different. Footballers are pragmatic.I am not sure the players ever really discussed it.
"Spurs never forgot the lesson, though, and they certainly never made the same mistake with a player’s contract again."
Sherwood brought the topic up because of two high profile players who Tottenham could potentially take advantage of to sign via the same ruling 14 years on.