If we trace its roots all the way back to the late 19th century, then football looks very much like a tribal sport. You had groups of men who shared the same neighborhood, the same family ties, or perhaps even the same occupation banding together to develop this new sport, and indeed even the notion of athletes as professionals. Given those intimate ties, it's not surprise players and fans were bonded to one club for life, sowing the seeds of all the great rivalries we enjoy today.
However, once the game became professionalized and players were tempted by larger paychecks or better working conditions, those bonds slowly started to erode, leading many players to do what was once unthinkable: crossing the party line and suiting up for one's rival.
Now, if you're a fringe player, it's not that big of a deal, but many big names have crossed some of the most tenuous divides in global football in recent times. Luis Enrique, Luis Figo, and Ronaldo playing for both Real Madrid and Barcelona, Zlatan and Balotelli for Inter and AC MIlan, Gabriel Batistuta, Claudio Caniggia and Oscar Ruggeri for Boca Juniors and River Plate. And then there's the curious case of Kenny Miller, who crossed the Old Firm line in Scotland not once but twice, playing for Rangers then Celtic then Rangers...and then Rangers again between 2000 and 2018.
Given the increasingly cosmopolitan nature of modern football, these perceived betrayals don't sting quite as much—though Ruggeri had his car and his parent's house allegedly burned by jilted Boca supporters—but it's still not a regular occurrence.
Roma and Milan aren't exactly direct rivals, but they are two of the more storied clubs in Italian football and have seen their fair share of players don both shades of red. While legendary striker Gunner Nordahl played for both the Rossoneri and Giallorossi back in the days of black and white photography and Cafu made the switch in the early 2000s, the recent history of players shuttling back and forth between the Olimpico and the San Siro is...uh...a mixed bag.
Since the two sides are colliding tomorrow, why not take a quick look at the gaggle of men fortunate enough to live in two of the world's greatest cities over the past 15 years or so? (Please forgive me if I forgot a few)
We don't need to rehash the Cassano and Roma melodrama again, but needless to say it was a disaster. Cassano had arguably the best stretch of his post-Roma career in Parma and Sampdoria, scoring over 50 goals, but Fantonio had a nice run in Milan, scoring seven goals in 33 appearances in the 2011-2012 season.
Stephan El Shaarawy
Again, another player with whom Roma fans are quite familiar. The Giallorossi's winter 2016 gamble paid handsome dividends, with the Pharaoh scoring 40 goals over parts of three seasons before cashing in and heading to China. His Milan career was really a flash in the pan, but total it all up and SES scored nearly 80 goals in his 11 seasons in Serie A.
The first man on our list who who moved direct Roma to Milan, Mexes was a fan favorite in the capital, forming arguably the club's best defensive pairing of the past 15 years with Juan. Roma definitely got the better half of Mexes’ career, but the Frenchman did make over 100 appearances (all comps) for Milan during his five seasons in Italy's fashion capital.
I'll be honest, I'm not even sure I can conjure an entire paragraph out of this one. There was a brief moment in time when it looked like Borini would be Roma’s next great forward—scoring nine goals in 24 appearances in Roma's ill-fated 2011-2012 season—but rather than nurturing that talent, they cashed in on Liverpool's €13 million offer. Borini would spend a few seasons in Sunderland before returning to Italy, signing with Milan in 2017, going on to score four goals in 51 league appearances.
Similar to Mexes, Roma definitely wrung the best out of Destro's career, squeezing nearly 30 goals out of Mr. Right before loaning him to Milan in the winter of 2015. Destro looked good wearing the number nine in Milan, but with only three league goals in 15 appearances, he was more sizzle than steak.
The jewel in the crown of the Luis Enrique experiment, Bojan was meant to find his footing in Rome, finally living up to all the potential he showed as a youth player with Barcelona. And truth be told, his Roma career wasn't as bad as we remember it—seven goals in 33 appearances during his lone season—but Walter Sabatini opted not to get bogged down in his complicated contract (Barcelona had an option to buy in 2012, an obligation in 2013 but Roma could purchase him outright for an additional €28 million on top of the €12 they already paid), loaning him to Milan instead, with the Rossoneri assuming Roma's spot in that awkward agreement.
Bojan would go on to play with Ajax, Stoke City, Mainz, Alves and, most recently, the Montreal Impact and is somehow still not even 30 years old.
This was by no means an exhaustive look, but for two of the biggest club's in the country, they've shared an odd assortment of riches, haven't they?