Antonio Cassano & Roma: A Lesson in Regret

Modern Man is plagued by many things, from mundane, superficial concerns, to matters of the heart and soul. No matter how deeply one looks, there is one inescapable truth, one facet of modern life from which no one is immune—regret. Whether we're talking about the simple what-ifs that plague our daily affairs, or deep-seated, life-altering decisions, dealing with regret is part and parcel of being a human being; you never get everything right, nor were you meant to; life is simply too varied and too chaotic to be mastered. Regret can crush souls, but it can also move mountains. The key is the manner in which one lets it control their thoughts and actions.

Part of what makes sports, or any social triviality for that matter, so important is that it offers us an escape from this persistent existential examination, solace from the storm of self-analysis. Watching grown men kick a ball around offers a slight reprieve from the arduous path towards actualization. But, and here is the twisted part, as humans we transpose our own anxieties and our own regrets on the institutions meant to grant us relief from this evolutionary nightmare; we question, we analyze, we argue, and we wonder what if. What if Baggio hadn't missed that kick in 1994, what if the Red Sox never sold Babe Ruth, what if Michael Jordan never played baseball? What if Ryan Gosling took that gig with the Backstreet Boys?

These questions ultimately bear no fruit, but we persist in asking them, not to find some sort of divination, but rather to explore alternate realities somehow better than the one in which we exist. As Roma fans, there is one regret constantly panging away in the recesses of our minds, one matter of unfinished business, one man who may have altered our collective fates, one man whose mere existence begs a simple yet unrelenting question. What if he never left?

Antonio Cassano and Roma, the mere mention of that man and this city conjures up the most virulent of emotions: hate, animosity, rejection, disbelief. The passions produced from this divorce are as complex and ineffable as the man himself, but, rest assured, most of them are negative. But this isn't a story about jilted lovers; this is a story about regret. Regret for a potentially epic career rendered merely above average, regret for a club deprived of further glory, and regret for the reassurance he provided to the Roman soul.

So, on this the eve of his latest return to Roma, we take a look at what might have been for the man who once proclaimed he'd walk back to Roma for a shot at redemption. What might Antonio Cassano have achieved for himself, for his club, and for his country?

All Roads Lead to Rome

I'm sure most of you know this story, so we'll keep it somewhat brief. Cassano, born the day after Italy defeated Germany in the 1982 World Cup final, made his pro debut at the tender age of 17-years-old with his hometown outfit Bari. It wouldn't take long for Cassano to make a name for himself throughout the peninsula, based as much on potential as actual production. Although he only scored a handful of goals in his brief Bari career, in terms of Italian prospects at the turn of the twenty first century, Cassano was the cream of the crop.

But the boy from Bari, affectionately known as Il Gioiello di Bari Vecchia, made enough of an impression for Roma to shell out ₤60,000,000,000.00 for Cassano's services in the summer of 2001, beating Juventus and Manchester United for his signature...remember the Lira? It always made things look so expensive, but at roughly €30m, Cassano was one of Roma's largest outlays ever; sixty billion lire spent on one player, and on a kid, no less. This wasn't a passing fancy, this was an investment; Roma was counting on Cassano to mature and flourish in the Eternal City, to team with their other prodigy and remake the face of the Italian game.

While Cassano's debut season in Roma was rather non-descript--only five goals in 22 appearances in the 2001-2002 season--he would soon settle in and begin to make his mark, forming an electric partnership with Francesco Totti.

Without a doubt, Cassano's best stretch at Roma was 2002 through 2005, a span of 91 matches in which Cassano scored 31 of his 39 goals for the Giallorossi. Of course, in the true Roma way, there were three managers at the helm during this period, so the manner in which Roma's #18 was deployed, and his scoring opportunities, varied greatly.

At times, particularly during the Fabio Capello era, Cassano was at the vanguard of a 4-4-2, seated to left of Totti, while, in some instances, he actually played in front of Totti, pairing with Vincenzo Montella in a 3-4-1-2. When Roma's managers opted for the 4-3-3, particularly during the forgettable tenure of Luigi Del Neri, Totti, Cassano and Montella graced the frontline together. There were also instances, rare as they were, in which Cassano played a more withdrawn and supporting role as a left midfielder in a 4-2-3-1.

No matter the formation, the genius rested within the chemistry between Francesco Totti and Antonio Cassano. Two young men, neither blessed with extraordinary physical gifts, yet each possessed such an innate understanding of attacking football, that their touches, their timing, and their movements belied their relative lack of athleticism.

While Cassano has always been lauded for his versatility and nose for goal, make no mistake, he was not brought to Roma to unseat Totti as the pivot upon which Roma's offense turned; Totti's 54 goals across Cassano's four seasons in Roma is testament to that fact.

But, if you need to know what made the prospect of Totti and Cassano so enticing, look no further:

While I wouldn't dare call it a causal relationship, Totti's ascendency as goal scorer coincided with the arrival of Antonio Cassano. Requiring little more than a telling glance, Totti and Cassano were able to unleash a devastating series of touches, flicks, and backheels, weaving in, around, and in between defenders. This once-in-a-lifetime tandem completely eviscerated any obstacle thrown in front of them; the future was theirs for the taking.

But, we all know what happened next; Cassano burned his first bridge...in spectacular fashion.

You're not coaching those useless players you had at Udinese. This isn't your house - it's my house.

These were Cassano's words to new Roma manager Luciano Spalletti, as he made the step up from Udinese to Roma. Throughout the summer of 2005-2006, Cassano was pining for a new, and presumably more lucrative, contract, as his original deal was set to expire at the end of the upcoming season.

Of course, given that animosity, the chances of working out a new contract were effectively null, further complicating Roma's attempts to recoup any of the sixty billion lire they shelled out for Cassano. Roma, happy to expedite Cassano's exit, accepted a measly €5m from Real Madrid for the then 23-year-old; a substantial financial hit for a club never flush with cash and a damning blow to Roma's plans for the future.

(Burned) Bridge Over Troubled Waters

Although he would score three minutes into his Madrid debut, due to poor conditioning and his caustic relationship with Fabio Cappello, whom he reportedly told to ‘fuck off' more times than anyone cares to remember, Cassano's three-year stint at Madrid featured only 19 appearances and two goals. It was, by any estimation, a complete and utter failure.

From there, Cassano would save some face, turning in four largely successful seasons at Sampdoria. Of course, in true Cassanata fashion, Antonio would not go quietly into that good night. After refusing to attend an award ceremony, and the ensuing arguments with club President Riccardo Garrone, Cassano's tenure in Sampdoria was effectively done. While it wasn't as bombastic an exit as his previous two stops, Cassano essentially made his own bed, wasting the most successful stint of his career for reasons unknown.

Following a complicated three-way transaction, Cassano soon found his way to A.C. Milan, for whom he toiled under relative anonymity during the 2011-2012 season, obscured by more talented teammates like Zlatan Ibrahimovic, Alexandre Pato, and Robinho. There was simply no room for Cassano in the starting eleven, which made his transfer request--placed in the wake of the sales of several key Milan players--even stranger. He didn't like his role, yet he was upset when the very players standing in his way were jettisoned? Wrap your mind around that one, if you can.

Nevertheless, Cassano got his wish, a transfer to the club he supported as a youth, Inter Milan. Unfortunately for Cassano, following one season at the Meazza under Andrea Stramaccioni, he simply was not in Walter Mazzarri's plans for the new Inter. And it was off to Parma where he remains....for now.

Roman Regrets

While we can and should credit Cassano for his rebirth at Sampdoria and his success at Parma--flaming out at Madrid has ruined many a man, after all--these are the small ponds of Serie A. What could Antonio Cassano have achieved at Roma? Would the intervening nine years have been any different for the club and the player?

To answer that question, we'll start where he left off, Cassano's last match for Roma: December 11, 2005.

On this evening, Luciano Spalletti started Cassano and Totti up top in the base 4-4-2, supported by Simone Perrotta, Daniele De Rossi, Alberto Aquilani and Rodrigo Taddei. So, when we talk about what might have happen, it's really a question of where would Cassano have fit in with the Roma squads after the '05-'06 season?

For a number of reasons, including the lack of forward options and mounting injuries, Spalletti utilized the now-famous Totti-inspired 4-2-3-1, with Roma's #10 supported by everyone from Taddei to Ludovic Giuly, to Cicinho, to Mirko Vucinic. In a direct sense, Cassano would have been a marked upgrade over any of those players in their respective 2007 forms. Just imagine the sight of Totti in his false nine role, dropping back and seeing Cassano, Vucinic, or Mancini running rampant through the attacking third. Spalletti's Roma teams were already lauded for their ingenuity, grace, and effectiveness, but throw Cassano into that mix, and that Roma could have been extraordinary.

Really, we could speculate for days where Cassano would have fit in with Spalletti or Claudio Ranieri's machinations, but with Cassano, Totti, Vucinic, Mancini, Perrotta, David Pizarro, Jeremy Menez, and even Luca Toni in the mix, there was no limit to the attacking options at Roma's disposal. Totti could have dropped back into the hole behind Cassano and Vucinic, or even remained at the top of the formation with Cassano, Vucinic, Menez or Mancini out wide and Perotta, De Rossi or Pizarro directly behind him.

The point, and the beauty of the Totti-Cassano pairing, was that they each possess such a unique blend of scoring and creating, such an exceptional understanding of the game, that formations tend to coalesce around them; there is no need for rigidity, they can be the agents of change or a piece of the puzzle.

And, let us not forget the impact Cassano's mere presence would have had on Roma's transfer market. With Cassano in the mix at center forward, there may not have been a need for Roma to dabble in the Julio Baptista market, to say nothing of their failed Adriano experiment. Could Cassano's presence have eliminated the need for Marco Borriello and his exorbitant contract? Would he have spared us the wretched sight of Stefano Okaka in the starting lineup? What about Pablo Osvaldo, would he have invaded Roma if Cassano was around? Would there have even been an Enrique experiment in the first place?

But that's Roma, what about Cassano himself?

Outside of his halcyon days at Sampdoria and his performance this season for Parma, what has he done that was so great? Has ever really made a mark? His first post-Roma experience in Madrid was an unmitigated failure, while his Milanese moments were few and far between. The magic he conjured in Roma, however fleeting it was, never saw the light of day in his more luxurious locales.

What could he have achieved alongside Totti for the past decade? Would he have become a perennial ten goal-ten assist man playing alongside someone as talented as Francesco Totti? Imagine Cassano at age 24--no problems, no egos-- playing the entire 2006 season under Spalletti's guidance, could he have made Italy's trip to World Cup glory a bit easier?

The mind wanders...

The Cassano Conundrum

Listen, there is a reason I wrote this and there is a reason you taking time out of your day to either read it or skip immediately to the comments and assail Cassano, he is an immensely talented player, inconsistencies and irreverence aside. Since his return to Serie A in the 2007-2008 season, Cassano has amassed 60 goals and 66 assists in 184 appearances; it doesn't get much more balanced and dynamic than that, now does it? This season alone, Cassano's 11 goals are tied for sixth in the league, his five assists place him tied for fifth, and his 2.7 key passes per match actually lead the league (as of week 30).

So what gives? Why is a player as gifted as Cassano, at 31-years-old, already on his sixth professional team? Why is someone so talented, so multifaceted, and so capable of killing a defense from every conceivable angle on his third team in as many seasons? Why has Cassano consistently burned every bridge built to carry his career to greater heights?

Well, for that answer, we'll turn to the man himself.

In a recent interview, Cassano was asked about the prospect of handling the whims and emotions of Mario Balotelli. While that is a matter for another day, Cassano, in drawing a parallel between himself and Super Mario, gave us a bit of insight into the mind of number 99.

I can only say one thing. Carrot and stick with Balotelli and take him as he is. Do not try to change him. He is a good guy. But he is a bit like me, I have to be taken in the right way. And I, too, in certain situations saw that the right way did not find me.

Far be it from me to indulge in arbitrary pop psychology, but if this quote doesn't smack of shifting blame, I don't know what does. The "right way" did not find him, as if forming a productive relationship is a one-way street.

But then, he hit us with this beauty.

The only teams I have to talk well about are Sampdoria, who remained in my heart, Inter and Parma. I don't give a damn about any of the other clubs I played for

The Sampdoria connection is obvious, they brought him back to Serie A and he scored 35 goals in the process, so that's all well and good. But take the two quotes together (and, in all fairness, they were from separate interviews on separate subjects) and they paint the picture of a petulant adolescent who steadfastly refuses to admit his own culpability in the deterioration of relationship after relationship.

So, it should come as little surprise that is constantly chasing something: teammates to support him, an opportunity to flourish, or simply a home. The real kicker is that he's had this chance, but pissed it all away time and time again, and for what?

Hindered by Hindsight

Cassano's song is a tired one; one we've heard from countless athletes, performers and those waiting for the crown, but when we're talking about sports, it resonates a bit more. Perhaps it's because we played the game ourselves--either as children emulating the moves and mannerisms of our heroes, or as adults, still carrying the illusion as a means to skirt the pressures of the real world, if only for a few hours on a Sunday--or perhaps it's because we wear their shirts, or decide their fates on our consoles.

Whatever the case may be, when we see athletes squandering or belittling that which we hold dear--the game, the crest, or even our failed dreams--our hearts ache just a bit, we become filled with animosity and plagued with regret. Not for what became of our lives, but regret that these men, these institutions meant to offer consolation, didn't evolve as we'd hoped.

It was one thing to turn his back on Roma for the more moneyed Madrid pastures, but to fail so spectacularly, to not even make a mark in Spain, made the manner and consequences of his departure, the regret for what may have been, harder to bear. We knew Antonio Cassano and Roma could have been a resounding success. We knew that Totti and Cassano could have rewritten the Serie A script of the past decade.

We knew that we missed out on something, but what exactly? Could Antonio Cassano have broken Roma's string of second-place finishes? What would have become of his partnership with Francesco Totti? Just how great could Cassano have been in Rome?

We'll never know, and that is precisely the point. We despise Antonio Cassano, but not because he's selfish or immature, but because he robbed us of that chance, of that dream, of those expectations, leaving us instead with an unremitting sense of regret.

So, when Cassano takes the field at the Olimpico on Tuesday, try not to dwell on what might have been, but appreciate what was; because it was beautiful.