Liverpool's new owners were left with no doubt about the size of the task ahead as Everton won the 214th Merseyside derby 2-0 at Goodison Park.
John Henry, head of New England Sports Ventures, was at Goodison Park to witness first-hand a fiery encounter which Everton dominated for long periods and deservedly won.
Goals from Tim Cahill and Mikel Arteta did the damage either side of half-time as the hosts out-played and out-fought their near-neighbours.
The defeat left Liverpool in 19th place in the Premier League, with only a solitary victory over West Brom in eight games.
And their worst start to a season since 1953/54 - when they were relegated - undoubtedly got worse with defeat against a team who were only a place above them before the start of play.
One thing is certain and that is the new American owners, who invested heavily in the Boston Red Sox when they acquired the baseball team in 2001 prior to two World Series wins, will have to come up with funds for manager Roy Hodgson to strengthen in January.
All the focus, as it had been for the preceding week, will be on Liverpool's failure but Everton were worthy winners, ending a run of three successive derby defeats.
The opening 45 minutes were in keeping with most Merseyside derbies, with the first late tackle coming after just 11 seconds and several more proliferating the half.
Maxi Rodriguez and Raul Meireles earned themselves yellow cards while Tim Cahill was booked for Everton as World Cup final referee Howard Webb tried to exercise restraint.
The actual football action was very limited with Arteta hitting a 20-yard free-kick into the wall and Everton centre-backs Phil Jagielka and Sylvain Distin both having half-chances with shots from inside the box.
Prior to Everton's opening goal it was the visitors who had come closest to scoring with their first attack - although it took them 23 minutes to create one.
Joe Cole's left-wing cross picked out the fit-again Fernando Torres at the near-post and his flicked header forced Tim Howard to tip over his crossbar.
Meireles had a 25-yard piledriver blocked by a wall of blue shirts from a half-cleared corner but that was the most Liverpool threatened.
It was just after their all-too-brief best spell of the first half that Liverpool went behind.
A slack piece of defending by Lucas Leiva and Paul Konchesky in the 34th minute allowed Seamus Coleman to run to the byline and cross for Cahill to hook home at the near post.
It immediately sparked chants of 'going down' from the home fans.
Diniyar Bilyaletdinov replaced Osman for the second half, which was only four minutes old when Everton went 2-0 up.
Sotirios Kyrgiakos' headed clearance only reached the edge of the penalty area where Arteta was lurking to smash home a brilliant swerving volley.
Manager Roy Hodgson had spoken in the build-up of his hope of seeing his side not have to chase a game - which had cost them in previous matches - but now they had a mountain to climb.
Meireles' 30-yard shot failed to cause Howard any difficulty while Torres' effort from inside the area landed in the top tier of the Gwladys Street stand.
Joe Cole's inability to control a pass from Reina, allowing the ball to run out of play, summed up Liverpool's performance.
Everton continued to create the chances and Jagielka fired over from a corner in the last 15 minutes before substitute Jermain Beckford had claims for a penalty turned down after falling under a challenge from Martin Skrtel.
By contrast, Gerrard was woefully off target when teed up by substitute Ryan Babel on the edge of the penalty area while Torres shot straight at Howard when he should worked the goalkeeper more.
Beckford had chance to finish in style in added time but drilled his shot over.
This derby was billed as the most significant in three decades, considering the clubs' league positions.
Seasons do not succeed or fail on such occasions but it will prove a useful point of reference for Liverpool's new owners.
