Transfer drama is nothing new in world football, but Major League Soccer has had its fair share of near-misses that left fans stunned. Perhaps none more dramatic than the saga of Andrea Pirlo’s near-move to Orlando City in 2015 — a deal that was reportedly minutes away from being finalized before collapsing in shocking fashion.
At the time, Orlando City was desperate to make a splash. The club had just joined MLS, and while Brazilian icon Kaká was already their marquee player, management wanted another global superstar to elevate the brand. Negotiations with Pirlo, fresh off a Champions League final run with Juventus, looked promising. Reports even suggested that Orlando had a private jet waiting to bring the Italian maestro to Florida.
Then, the twist.
Just as fans began celebrating online, news broke that Pirlo had instead chosen New York City FC, signing a Designated Player contract alongside Frank Lampard and David Villa. The sudden reversal stunned Orlando supporters, who had been led to believe the midfield legend was theirs. For many, it felt like a gut punch — the kind of heartbreak only soccer transfers can deliver.
The fallout was immense:
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Orlando fans accused the front office of overselling the move.
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NYCFC instantly became a bigger draw, with Pirlo’s arrival sparking a surge in ticket sales and media coverage.
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MLS, as a whole, gained credibility, but Orlando was left wondering how close they’d come to changing their destiny.
Looking back, Pirlo’s stint in New York was a mixed bag. While his passing vision and technical brilliance were evident, his lack of pace and defensive work rate frustrated many fans. Still, the “one that got away” narrative remains alive in Orlando City circles.
As one Orlando supporter bitterly posted on social media after the collapse:
“We had Pirlo in our grasp… and then he slipped through like sand.”
It was a reminder that MLS, just like Europe, is a theater of transfer drama — where even the deals that don’t happen can leave a lasting mark.
