When you look back at the history of transfers in this sport, there are endless examples of; "would've, could've or should've" over the years. Liverpool Football Club are not exempt from this either, as there have been some major transfer sagas over the years in which the Reds could have been totally altered.
In this new series, we will jump back in time and turn things on their head. We'll explore what might have happened if the alternative option had come to fruition.
With that in mind, we begin our 'What If?' series traveling back to the summer of 2008. It was a different time, and Liverpool was on the hunt for one key target: English midfielder Gareth Barry.
Why Gareth Barry?
In the summer of 2008, Liverpool were coming off of a fourth place finish in the Premier League where they were 11 points adrift of champions Manchester United.
They were also Champions League semifinalists where their European journey ended at the hands of a spirited Chelsea squad. Rafa Benitez led his charges no further than the Quarterfinals in both domestic cups as well, so it was a trophyless campaign.
Fernando Torres and Steven Gerrard were the creative fulcrums for the Reds as their partnership was one of the most lethal in all of Europe.
The midfield also showcased Xabi Alonso, who was being courted by Real Madrid (Sound familiar?) and Juventus at that time. Argentine Javier Mascherano also featured 41 times in all competitions.

However, with the season concluded, Benitez could see the writing on the wall for an eventual Alonso exit and he was desperate to find a suitable and proven replacement for his midfield anchor. That brings us to Gareth Barry.
At the time, Barry was 27 years old and just entering his prime. He played 40 times for Aston Villa in the 2007/08 season while recording 9 goals and 13 assists.
He was a rock solid player that could breakup play on one end and get things moving on the counter without issue. While his game might have lacked flair, it offered a solidity that Benitez thought was missing from his midfield.
A natural fit at Anfield?
Liverpool fans are some of the most knowledgeable football fans in the world. We understand when things are off and if something has to change.
With that in mind, there was obviously nobody that was going to displace Stevie in midfield, as it would have been blasphemous to even broach the subject. However, for all of his flair and genius on the ball, Xabi Alonso did not always provide the security needed behind a marauding Gerrard.
Don't get it twisted, watching Xabi ping a 60-yarder to Torres or Dirk Kuyt on the wing with ease was some of the most brilliant stuff to watch at that time from Liverpool.
Yet, had Barry been brought into the side, could he have unlocked another dimension to his game? A midfield trio of Gerrard-Barry-Alonso might have checked all the boxes we as fans, and more importantly Rafa Benitez, were looking for.

Barry was tidy on the ball and rarely flustered as he was one of the best at that time at retaining possession and keeping things moving.
He could sit at the base of the midfield and let Stevie work his magic but also allow Alonso to get further upfield where his scintillating passing skills would have surely unleashed a whole new world for the Reds attack.
Could that stability and trust in midfield helped turn around the runner-up finish the following season? It's impossible to tell, but Barry's presence and leadership in that Liverpool midfield would have stemmed a lot of tides.
What Went Wrong?
I must admit, at the time, seventeen long years ago, I was a teenager checking the daily reports on this saga. I was very much in the 'Pro - Sign Barry' camp and I was loud and proud about it.
Youthful exuberance could not foresee the behind-the-scenes debacle that would have to take place to see this transfer never come to fruition.
Liverpool wanted to acquire the England International for a fee no more than £15 million which equates to around £26m in today's market. While that seems paltry by today's robust transfer standards, it was truly a substantial investment in a deep-lying midfielder at that time.
Villa were firm they would not move their Captain for less than £18m. Looking back, haggling over such a minute difference in valuations does seem way too familiar.

Then Villa manager Martin O'Neill lashed out at Benitez for comments on the transfer saga which only added fuel to the fire and made both sides dig their heels firmly into the ground.
When I tell you the daily frustrations I had with Tom Hicks and George Gillett for not just giving the Villains what they wanted were over-the-top, it's an understatement.
The entire transfer saga actually revealed a lot about where Liverpool would go only a few short years later and what we could expect.
At that time, Liverpool fans were justifiably becoming frustrated over how the club was being ran and Barry became the flashpoint for this debate.
Whether or not it made sporting sense to sign him, the club's refusal to pour out an ounce over their limit only reinforced what we already knew, change was needed at the very top.
Repercussions and What could have Been?
At the end of the day, Gareth Barry stayed at Aston Villa for the 2008/09 season where he played almost 50 times being the steady and reliable player we all knew him to be.
He would move to Manchester City the next summer for only £12m which was a slap in the face to a younger me. It was probably the first time I really began truly loathing City and it was over a player that never played a minute for us!
Xabi Alonso would also only stay one more season with Liverpool as he was clearly shaken with Benitez being so willing to part with him to raise more funds to get Barry in the door.

Had Reds' ownership ponied up and spent a little extra to sign Gareth Barry and retain Xabi Alonso, it would have done several things. I already discussed what it could have looked like at Anfield, but what about elsewhere?
He instantly became a stalwart for City and played the full 90 minutes or extra time in 40 of his 43 appearances in all comps. This would carry over the next few years as he was a key component in their rise to power in England culminating with the 2011/12 Premier League title.
However, if he was plying his trade at Anfield, he never provides that leadership and quality to the City midfield and it would have been very interesting to see how they would have fared.
Conclusion
If Liverpool had been able to comfortably sign Gareth Barry in the summer of 2008, the outlook over the next several years might have been different, at least on the pitch.
They would have had the most balanced and gifted midfield in the Premier League sitting behind a lethal finisher in Torres. Perhaps Xabi Alonso is not as motivated to move on and stays longer?

City never get one of their first leaders of the new era we have come to despise to this day and who knows how that would have changed their trajectory. Watching him win trophies at Manchester City before eventually joining Everton, knowing he could have been ours, was almost too much for me.
I was so invested in the saga I probably saw him as more of a game-changer than he might have been. He was a really good player, but he did have his limitations.
Yet, sometimes being a football fan means you think with your heart and not your head. My heart told me Gareth Barry was perfect for Liverpool. Yet, that would not have stopped the financial crisis that resulted from poor ownership.
Ultimately, it would have been a good move for Liverpool but not the end-all-be-all. We would have been a better side with him in it at that time, but the long-term prospects probably don't change much.
At the very least, they would have made a very passionate 16-year old LFC fan at the time very happy. But hey, they gave me great content to harp on almost 20 years later, so that's a win, right? Right?