Originally joining Chelsea as director of football in July 2007, Grant was elevated to the front of house when Jose Mourinho departed that September.
Replacing the 'Special One' would be no easy feat, but Grant, whose CV was relatively modest in comparison to Mourinho's, quickly declared himself his own man.
Unbeaten in World Cup qualifying with his native Israel, Grant had also managed with some success in his homeland, but never in one of Europe's top leagues, though he had been director of football at Portsmouth in 2006/07.
The fixture list had not been kind for his Premier League baptism, and Grant's first game in charge was at Manchester United, where refereeing decisions went against us - a first-half injury-time opener and a harsh penalty followed John Mikel Obi's straight red card for what looked no more than a solid tackle.
The Chelsea support was understandably frosty to begin with, but a Champions League victory in Valencia and a 6-0 drubbing of Sven Goran Eriksson's Manchester City began to turn the tide as we re-entered a title race that had looked beyond us early in the season. He was awarded with a four-year contract in December.
This in spite of a deepening injury crisis that at one time or another kept Petr Cech, John Terry, Ashley Cole, Michael Ballack and Didier Drogba from action, while the Africa Cup of Nations then took four first-team members to Ghana for a month.
In their absence, Grant managed to unite his men and grind out a series of five straight league victories post-Christmas, reaching the Carling Cup final thanks to aggregate victory over Everton.
February though would not be enjoyable, as draws with Portsmouth, Liverpool and Olympiacos preceded extra-time defeat at Wembley to Spurs, Grant out-thought on the day by Juande Ramos.
The reaction in the next game at West Ham was strong, as a 4-0 victory provided two Goal of the Season contenders from the consistent Joe Cole and Ballack, whose January form had been sensational. The Greeks were also brushed aside at Stamford Bridge, and with a last-eight tie against Fenerbahçe, European success became a real possibility.
Just three days later though came Grant's nadir. With Man United, Liverpool and Arsenal already eliminated, a successful defence of the FA Cup looked likely - but a 1-0 defeat at Barnsley, in which he had rested some of his main men, put paid to that dream.
Widespread criticism followed but again Grant bounced back, Frank Lampard doing the damage with four as Derby were hit for six, and then a 1-0 win at Sunderland brought us within three points of the Premier League summit, nine games remaining.
Spurs again threw a spanner in the works, coming back again and again to earn a 4-4 draw before Grant's major tactical success came against Arsenal. Trailing 1-0 at Stamford Bridge he brought on Juliano Belletti and January signing Nicolas Anelka, who had struggled to make an impact in Chelsea colours, and the game turned, the Brazilian laying on one for Drogba, the Frenchman the other, as we went second in the table.
In Europe a Champions League defeat in Turkey was overturned in London two weeks later, meaning a semi-final date with Liverpool for the third time in four years.
Still Grant was unpopular in the press, less charismatic than his predecessor, and things were no easier after a monosyllabic press conference following victory at Everton, the manager seemingly unhappy with criticism he had received in the wake of a draw against Wigan. Five days later we were back on Merseyside and John Arne Riise's injury-time own goal turned the tie on its head - a home victory would be enough to reach Moscow.
League victory over Man United put us level with the champions, albeit lagging on goal difference, before Liverpool were finally beaten after extra-time, Lampard and Drogba seeing us through to Moscow, Grant pictured on his knees pointing to the heavens.
We would meet United in Moscow, but first they were to claim a second successive league title by winning at Wigan on the final day.
For long periods we were the better side at the Luzhniki Stadium, but by the end of the penalty shootout Grant cut a despondent figure, the dream in ruins.
Four days later he left the club, eventually replaced by Luiz Felipe Scolari.
Grant will likely be remembered as the nearly man, who came so close to bringing that first Champions League success, but in the end departed empty-handed, a runner-up three times, his success in making us competitive not enough to compensate his shortfalls in charisma or experience.
After a spell out of the game, he re-emerged at Portsmouth, whom he would lead to the 2010 FA Cup Final where again he would be denied at the final hurdle - this time by Chelsea.