Sotiros Kyrgiakos replaced Sami Hyypia.
Alberto Aquilani filled the shoes of Xabi Alonso.
Alvaro Arbeloa was swapped for Glen Johnson.
Liverpool's transfer outlay in the summer of 2009 - now a decade ago - reads like a manual on how not to go about your business.
Rafael Benitez , whose dealings in the market were coming under increased scrutiny, splashed out on Aquilani and Johnson with the money recouped from Alonso and Arbeloa's double-exit to Real Madrid.
The Spaniard, of course, had no idea of what was to come.
Liverpool would fail to make it out of the Champions League group stages while also suffering a humiliating third round FA Cup replay exit to Championship outfit Reading at Anfield.
A seventh-place finish meant the Reds failed to qualify for Europe's most prestigious competition for the first time since 2003 while off-field chaos involving the much-maligned George Gillett and Tom Hicks hardly helped matters.
Less than a year after Aquilani arrived from Roma, Benitez was sacked .
"Rafa will forever be part of Liverpool folklore after bringing home the Champions League following the epic final in Istanbul but after a disappointing season both parties felt a fresh start would be best for all concerned," then-chairman Martin Broughton said.
The former Real Madrid and Inter Milan manager may, in times of contemplation, reflect upon that final, fateful summer.
Aquilani, who, in fairness, struggled with injuries during his time on Merseyside, made just 18 Premier League appearances before being farmed out to Juventus on loan the following campaign.
Johnson was a regular for Liverpool until he joined Stoke City in 2015 and Benitez did, perhaps, get his money back on a £17.5m signing.
The right-back made 200 appearances at Anfield and played 29 Premier League games for Brendan Rodgers as the Reds came within a whisker of winning the title in 2014.
The less said about Kyrgiakos, however, the better.
He struggled to hold down a starting place during Benitez's final campaign and his two seasons on Merseyside coincided with some of the worst team performances in recent memory.
Unsurprisingly, neither the Greek nor Aquilani achieved much more after departing Anfield and Johnson played out the final years of his career dependably on the Potteries .
Alonso, meanwhile, lifted a La Liga title in Madrid as well as a second Champions League following his Istanbul triumph. Arbeloa won two before ending his career with a brief spell at West Ham United.
Hyppia retired at Bayer Leverkusen to become first-team manager and has since enjoyed stints at both Brighton & Hove Albion and FC Zurich of Switzerland.
Jurgen Klopp , of course, does not have the problem's Benitez faced a decade ago.
Liverpool supporters made their peace with FSG after witnessing the flourishing relationship between owner and manager that has helped proper the team to Champions League glory.
Benitez's reign petered out. A mixture of misfiring transfer dealings , off-field drama, staleness and, at the bottom line, failing to win football matches meant his tenure ended under a cloud.
Liverpool's continued process of long-term planning and thinking in the current market means that the same fate will not, surely, befall Klopp.
The big picture is never out of focus under Klopp, with much-vaunted sporting director Michael Edwards operating closely alongside chief scout Barry Hunter and head of recruitment Dave Fallows, who have also seen their work hailed over the last three years.
Aquilani, Johnson and Kyrgiakos will not trouble too many pages of the history books. A decade on and they are, apart from pub quizzes and throwback discussions, largely forgotten.
But step-by-step, the Reds have learned from their errors in the market.
And this summer should once again prove that the mistakes of a decade ago are a long time in the past.
