And so the inevitable happened: Real Madrid eventually got their man.
After months, indeed years of on-off specualtion about a return from Anfield to Spain, Florentino Perez finally ended his pursuit of Alonso whilst blowing all the other fish out of the water with a massive bid; something Juventus had failed to achieve last summer.
The tremors leading up to the transfer were clear. Benitez had before proved willing to sell Alonso, but only at the right price, and Alonso was desperate to go. And so, the £30m figure reached after weeks of intense negotiation proved to be that magical number everybody wanted to hear.
Of course, the majorityof Liverpool fans won't be happy to see the back of a player who has become a firm fan favourite during his time in Anfield. His consistent performancs last season arguably, in hindsight, justified Benitez's decision to keep Alonso at the prospective loss of Gareth Barry.
As for Real Madrid his new club, well if I'm honest Alonso, a regista in the Pirlo mould, is not the type of player I believe Madrid absolutely need if they're going to be successful in Europe.
On the other hand for Liverpool, Alonso was a player they probably absolutely needed to be successful. (And I mean top of the table after 38 games successful, not the Roy of the Rovers cup runs that Liverpool have become adept at accomplishing).
Why is the loss of Alonso so detrimental you ask?
Firstly, there are no ready-made replacements for Alonso in the Liverpool squad.
Granted Gerrard can do everything Alonso can do, it would be a sacrifice for Liverpool at this stage pushing Gerrard back in front of the big four, especially considering the scoring prowess he's displayed in recent seasons.
Lucas Leiva?—Complete donkey, scratch that, complete joke I'm afraid: perhaps the only hilarious thing about Leiva for Liverpool fans is maybe that he himself doesn't know it yet. Once in a blue moon performances against shambolic teams like Newcastle United don't do it for me: They shouldn't be enough to convince Benitez either.
Secondly, Alonso's boot is the pivot on which Liverpool base their attacking game. Tactically positioned alongside Javier Mascherano, Alonso provided great balance to the midfield.
Like Pirlo who had a similar 'bulldog' partner in Genarro Gattusso for Milan, Alonso was free to playmake to his hearts content and one thing we all know Alonso possesses is an extraordinary long range passing ability.
The timing of the transfer also leaves little time to adapt before next season. It would be hard now to imagine Benitez scrapping the system he has spent 5 seasons perfecting at Liverpool since Alonso arrived. In a sense, Liverpool has had one of its vital organs removed with the conclusion of this transfer and a transplant may be too late.
Finally the replacement mooted, Roma's own Alberto Aquilani, is dubious.
As a Roma fan I found it surprising Aquilani was offered a pay increase with his recent new contract, despite his horrendous injury record ever since...well ever since he broke into the first team come to think of it.
25 year old Aquilani, even fit, was not the answer to Roma's problems, nevermind Liverpool's problems.
While hanging a 'work in progress' sign over the home dressing room at Ashburton with the blooding of youth players is a luxury afforded to Arsene Wenger, based on his past success, it is not really a luxury afforded to Benitez who has never had a success in the Premiership.
Traditionally Benitez hasn't prooved great at bringing youngsters into Liverpool's first team anyway by any stretch. Aquilani is a risk Benitez and Liverpool really don't want to be taking in this make or break upcoming season.
As Gillett and Hicks proved with the Jurgen Klinnsmann debacle, they are only to willing to see the back of a manager that has given them much grief over the transfer kitty.
And so with a month to go in the transfer window and less than a week to the start of the season Liverpool must readjust to the loss of a crucial cog in the Liverpool machine.
Can Benitez ease Aquilani into the team smoothly. Will Liverpool change their setup to cope? Can existing squad players step up to Alonso's former mantle at various points of the season?
There are too many questions for anyone to be comfortable with Liverpool's title hopes now I'm afraid.
You'll never walk to the top of the league come May without Alonso, Liverpool. Instead Liverpool may find themselves sprinting with Arsenal and City for the Champions League places in the final run-in.