In switching Arsenal red for AC Milan vermilion in the summer of 2008, Mathieu Flamini was making a statement.
The Frenchman, 24 at the time, was coming off a season in which he'd strung together his finest form as a professional to date for the Gunners, becoming the unequivocal first choice in the central defensive midfield role.
Flamini had been with Arsenal since 2004, when he'd moved on from Marseille. Interestingly enough, his picture on his Wikipedia page is of him in an Arsenal uniform, right hand raised in a wave. Was he waving goodbye? Maybe—if so, it'd be a fitting bit of foreshadowing, but more on that later.
During that 2007-08 season, it was Flamini's pluckiness and willingness to partake in the "dirty work" that allowed a then-burgeoning Cesc Fabregas to enjoy one of his best seasons to date. Flamini was no talentless brute, mind you. Even then, he was an above-average passer and had a knack for the odd goal.
With Flamini taking care of the defensive chores (I remember during the winter of that season, his jersey would always appear muddied within 10 minutes of play), Fabregas was given freedom to roam, as we saw him do to such devastating effect in subsequent seasons.
In 2007-08, Fabregas was named to the PFA Team of the Year and was named PFA Young Player of the Year (he was 20 at the time). Both awards were won in no small part due to the Spaniard's brilliance (he had 13 goals and a career-high 22 assists), but Flamini deserved some recognition for those honors as well. Those two often appeared a perfect combination during Arsenal matches: Flamini's defensive duties allowed Fabregas to wax his influence where he was most dangerous—in an attacking role.
Flamini missed out on PFA Team of the Year designations (given Steven Gerrard's sensational form for Liverpool that season, inclusion was always going to be a tall order for any other EPL mid), but his country had taken notice of his impressive form. Flamini earned several call-ups for the French national team that year and narrowly missed out on making the 23-man roster for Euro '08.
That setback didn't seem too problematic at the time. Flamini was just entering his prime, and he looked every bit ready to grow into Patrick Vieira's enforcing role in central midfield for Les Bleus.
Flamini was tough, resilient and possessed an abundance of technical ability and impressive mobility in navigating the pitch. He was, in a word, the epitome of the modern midfield enforcer, the likes of which we now see patrolling the Premier League as secure sentinels.
But back to his decision that summer: Since leaving Arsenal, Flamini has seen his career stagnate.
Perhaps "stagnate" is a bit harsh. It might be more fitting to say that his once-luminous star has dimmed ever so slightly. His career arc, once as spiked as a man's pulse after consumption of a Red Bull, has petered out to the after effects of drinking green tea. And serenity has no place in an ambitious man's mind.
Flamini has been excluded from the French national team discussion for quite some time now, and even at Milan he struggles to make himself an incontrovertible starter.
He has a healthy number of club appearances, but starts are a rarer treat. As the 2009-10 season came to a close—Flamini's second with Milan—there were even rumors he might be leaving the Rossoneri due to lack of playing time.
Despite seeing his career somewhat scuppered, Flamini stuck it out in Milan and was rewarded with helping lead the side to the 2011 Scudetto, the club's first in seven seasons.
The Frenchman even scored the winner in a crucial 1-0 win over Bologna on May 1st that sent the Lombards eight points clear of second place Inter Milan with just three games remaining.
With that strong finish fresh in Milan management's minds, perhaps 2011-12—the penultimate season of Flamini's contract—was destined to be his best yet. But his body got in the way of that hope.
Knee surgery has kept Flamini out since late August when he suffered ligament damage while playing against Juventus in the August Belusconi Trophy match. While he is nearing a return to the sidelines, there's still some time left before he can make the team sheet.
This means that when fate collides and Arsenal come to Milan to face the Rossoneri in Wednesday's Champions League Round of 16 first leg, the midfielder will be forced to watch from the sidelines.
It would have been an interesting reunion of sorts, to say the least.
Flamini was believed to have left Arsenal in a huff after the 2007-08 season in part because Wenger had not offered him a new contract before the season. Once he'd "proven his worth" by way of a highly successful season, he wished to find another club rather than sign an extension to keep him in London Colney.
But that plot line has now come full circle. Flamini signed a four-year deal with Milan in 2008, yet has never signed a prolongation.
With his contract now set to expire after the current season, there are rumors that Flamini might just come back to London and rejoin Arsenal.
A free transfer back to the club he'd left on...a free transfer. The times, they just aren't a'changin' it seems. Old is the new "new."
You just couldn't draw these things up.