Sliding Doors: What if Liverpool had signed Gareth Barry in 2008?

Not too many title bids, it’s fair to say, begin with a mega-money summer transfer fiasco. Yet nine years ago, Liverpool’s began with two. In 2008/09 Rafael Benitez’s Reds came within four points of the title, losing out to a Manchester United side that was arguably Alex Ferguson’s greatest ever.

But a season which so nearly ended in glory had started in disarray, with Benitez’s summer-long dual project of wooing Gareth Barry and shipping Xabi Alonso off to Italy having hit an impasse. On deadline day, a new suitor for Alonso made himself known.

“I was really close to Arsenal,” the midfielder recalled last year. “Benitez was open to me leaving. He showed me his cards – very clearly. I said to him: ‘Of course, Rafa, I accept this.’ But in the end nothing happened. Liverpool were asking for £18m and they were offering £15m.” For a relative pittance more, Alonso would have been the property of Arsene Wenger.

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Quite how Barry would have filled Alonso’s boots is one of life’s great unknowns. Stewart Lee once imagined James Corden watching one of Lee’s routines to be “like a dog listening to classical music”; some of Barry’s harsher critics on the Kop might have drawn similar parallels to him watching Alonso play. But if Benitez’s failed courting of the England man had caused a stir on Merseyside, one of his successful pursuits soon proved equally taxing.

Robbie Keane had arrived from Tottenham on the back of the best season of his career, yet it quickly became apparent that, with Steven Gerrard reinvented as a free-roaming forward alongside Fernando Torres, there was no place for the Irishman in the side. He was duly ushered out the back door six months later, returning to White Hart Lane for a £7m loss.

By then, though, the best Liverpool team of the modern era were on a title charge – evidence either that Benitez fluked his way towards near-glory, or of the old Brendan Rodgers maxim that football management is “like trying to build an aircraft while it’s flying”, a hugely imperfect science performed on the hoof. Either way, the ramifications of Benitez’s transfer dalliances that summer reached far and wide. And oddly enough, perhaps the least affected party of all was Liverpool, who were able to enjoy Alonso’s wily genius for another ultimately trophyless season before seeing him dispatched to Real Madrid anyway. Keane on the other hand, came and went having barely left a mark.

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For Arsenal, though, the 2008/09 season was a rather more seismic one in that it marked what we can now identify as the beginning of the late-Wenger decline. The previous campaign had seen a sparkling side lead the table in late-February, only to fall away in the wake of Eduardo’s leg-break. The consensus was that a cool, experienced head was needed to bring out the best in a brittle but skilful side in which the lavishly gifted Cesc Fabregas was too often expected to act as a one-man midfield.

Hindsight is a wonderful thing, but it’s hard to imagine a world in which the recruitment of Alonso for an extra £3m – or two-thirds of a Denilson – would have been anything other than a godsend to Arsenal. Instead the Brazilian played 51 games alongside Fabregas during a season in which the club slipped from title challengers to manful fourth-place battlers. It’s a role they’ve become accustomed to. (Their chief rivals for the final Champions League spot, incidentally, were a Barry-powered Aston Villa – a contest that would presumably have been rather easier had Alonso joined in the summer.)

Across north London, the realisation was dawning that Robbie Keane had become part of the time-honoured tradition of formerly free-scoring strikers dealt irreparable damage by a big-money move to Merseyside. When Keane left Spurs, it was as one half of the best strike pairing in the country alongside Dimitar Berbatov. The 12 months after he rejoined saw him, Darren Bent, Jermain Defoe, Roman Pavluchenko and Peter Crouch endlessly reshuffled in the vain search of a viable partnership; it concluded with a misfiring Keane being waved off to Celtic, and Harry Redknapp attempting to solve Spurs’ attacking woes by shifting a speedy young lad called Gareth Bale up on to the wing. Bale’s blossoming, and his subsequent £90m sale, laid the foundations for a sea-change that has seen Spurs conquer not just north London but, in the wake of Sunday’s success at Stamford Bridge, the entire capital.

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The stagnation that defines Arsenal’s last decade is the product of myriad factors. Yet if it’s possible to trace it all back to a clear fork in the road, it came in the summer of 2008. For the sake of penny-pinching the club passed up the chance to nab a high-grade player from their close rivals, and instead became the regular victims in that dynamic: the following summer Emmanuel Adebayor and Kolo Toure joined a newly moneyed Manchester City, thereby kicking off a near-annual Mancunian migration.

Would the signing of Alonso have really sparked a second imperial phase for Wenger’s Arsenal? Such conjecture is wildly simplistic: the oil-money era that’s left the Frenchman for dead was a good half-decade under way by that stage, and indeed Sheikh Mansour’s takeover at Manchester City was confirmed on the very day of Arsenal’s failed bid for the Spaniard. Perhaps, even if Alonso had gone to the Emirates and excelled, he would have soon been cherry-picked by a superclub anyway – or perhaps he’d have stayed at a rejuvenated club for the long haul, and Real Madrid would never have gotten their hands on their best midfielder in a generation.

As for Barry, the man who lost out on his big move in 2008 could have few complaints in the end. The following summer he did the in-vogue thing and, along with Adebayor, Toure and the rest, jumped aboard the City bandwagon. Three seasons later he was a Premier League champion, the unglamorous mainstay of an imperious midfield. Maybe Benitez was onto something after all.

Sliding Doors: What if Liverpool had signed Gareth Barry in 2008?
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