His final season was a disappointment, but a look at Liverpool's struggles since his departure sums up how lucky fans had it for the majority of his tenure. Like most managers, Benitez liked to take advantage of the transfer market, but he didn't always quite get it right.
As he prepares to spend one of football's biggest chequebooks in January, here is a look at 10 signings which could have worked out oh so differently.
Robbie Keane hasn't been a bad player, he is Ireland's record goalscorer of all time after all. But his time at Liverpool was a strange one indeed. He was signed from Spurs for £20 million, but failed to click up front with Torres. Nevertheless, Benitez pulled the plug too early surely, selling him after six months, for £12 million, taking in a big loss. His failure to sign another striker left Liverpool short up front for the title run-in, placing too much pressure on Torres, forcing the manager to play him when not 100 per cent fit.
Dutch defender Jan Kromkamp described his move to Liverpool as a 'dream move' when he signed in 2006. Sadly it didn't work out that way, he made just 17 appearances for the club, mostly from the bench, and was criticised for his lack of playing time by his national team coach Marco van Basten, who dropped him from the international side. He was sold just six months after his arrival to PSV and now plays for Go Ahead Eagles.
Even though he was signed on a free, Liverpool still seemed to get ripped off when signing Voronin. The Ukrainian regularly frustrated Reds's fans with his wastefulness in front of goal, and was never really considered a regular starting option for the club. Liverpool impressively managed to sell him for £4 million in 2010 to Dynamo Moscow.
Aquilani was Benitez's last great folly. With just a £20 million budget to rejuvenate the side who narrowly missed out on the title in 2008-09, the following summer he decided to spend £17 million of it on Aquilani, even though the Italian's injury problems should have stood out as a major red flag against it. His gamble backfired, as Aquilani's injury troubles struck, and it took him three months to make his debut. The player never settled, and within a year, Benitez left the club.
"I am confident he will be prove to be a quality addition to our squad." - Rafa Benitez, 2008. Not for the first time, Benitez would be proved wrong. Degen struggled with injury - taking 14 months to make his league debut, and in the few starts he did have, looked out of place. Despite being signed on a free, his wages consitututed a waste of money and his contract was terminated by mutual consent in 2011.
Ryan Babel was touted as the next big Dutch star, signed for the relatively substantial fee of £11.5 million. It didn't work out, with Babel similarly wasteful to Shaun Wright-Phillips in attack, and his off-pitch attitude was credited with failure to fulfil his potential. His winner over Manchester United in 2008 will live on in the memory. At 25, he was a free agent this summer, and headed back to Ajax with his tail between his legs.
Morientes' signing at Liverpool was seen as an outstanding piece of transfer business, he had been excellent for Real Madrid, and on loan at Monaco too. Yet the £6.3 million they paid for him, while it should have been a bargain, proved to be money badly spent. He scored just eight goals in 41 appearances and was sold after 18 months at the club.
Dossena cost Liverpool £7 million, and one unlikely goal against Manchester United aside, he looked out of place in an otherwise solid 2008-09 Liverpool side. After falling out of favour he made just 30 appearances in two seasons, and was sold to Napoli after losing his position to Fabio Aurelio.
Paletta was signed for just £2 million by Liverpool, with the expectation the young centre-back would go onto become one of football's next big talents. He was after all a member of an Argentina youth side boasting Lionel Messi and Sergio Aguero. The Argentine was handed the odd League Cup appearance and substitute showings, but the Reds lost faith in him after just a season, allowing him a transfer back to his homeland with Argentina. He currently plays in Serie A with Parma.
Nunez was one of the low-profile faces to arrive in Benitez' early years, as part of his Spanish revolution, in the deal which saw Michael Owen sold to Real Madrid. He lasted just a single season at Anfield, underwhelming fans, even though he scored a consolation in the 2005 League Cup Final. Nunez now plays for Spanish second division side Huesca.
Who was the worst? Who have we missed?
image: © vincentteeuwen