Oops, Italy Did It Again, Again!

There are many ways to frame what I'm about to say, and I'm sure someone funnier and smarter than me could find the perfect way to really maximize the impact of this sentence. I, however, think the bold-faced truth, with no embellishment, is the funniest way to deliver this news, and so: For the third straight time, the Italian national team has failed to qualify to the World Cup.

Thanks to two losses to Norway in UEFA qualifier group play, Italy botched its initial qualification process for the 2026 World Cup, capped in embarrassing 4-1 blowout fashion back in November, at home no less. That meant the Italians had to navigate two one-leg knockout matches to keep the hopes of a return to the World Cup alive. The Azzurri did dispatch Northern Ireland 2-0 in Bergamo on Mar. 26, while Bosnia and Herzegovina beat Wales in a penalty shootout on the same day. That set up Tuesday's win-and-you're-in showdown in Zenica, in front of a rowdy Bosnia crowd that was no less fervent in the face of a capacity reduction handed down by FIFA, due to previous incidents in a match against Romania last year.

At first, it looked like Italy would shake off the World Cup ghosts that have haunted them for the past decade. About a quarter of an hour into the game, Bosnian keeper Nikola Vasilj misplayed a pass out of the back directly to Nicolò Barella, who swung it to Moise Kean, who first-timed a well-struck shot that curled into the back of the net to put Italy up in the 15th minute:

Following the goal, Italy looked in control. A level-headed performance from there on would likely have been enough to keep Bosnia out and secure qualification and—oh no, Alessandro Bastoni has received a red card:

It's unfortunate to pick on Bastoni, one of Italy's best players, but pick on I shall. You can't do that. You really can't do that in the first half of a do-or-die World Cup qualification match:

Bastoni's was the type of tackle you either have to get spot-on or reserve for second-half stoppage time while clinging to a lead. It's definitely not a tackle you should attempt with 50 minutes left in a match of this caliber. While Italy saw out the last few minutes until halftime without incident, the atmosphere in the Italian locker room must have been dire.

And yet! Ten-man Italy actually came out to play in the second half. The next best chance came from the opening goalscorer as well. On the hour mark, Kean rocketed through the Bosnian defense on a solo counter-attack run, holding off two defenders only to sail the shot over the bar. Unfortunately for the Fiorentina man, he'd come to regret that.

In the 79th minute, Benfica right back Amar Dedic squared a cross to the far post that just floated over Haris Tabakovic's head, falling directly into the path of Bosnian legend Edin Dzeko, who forced a valiant save from Gianluigi Donnarumma. Unfortunately for Italy, the ball then fell to Tabakovic, who nudged it home for the equalizer. Cue pandemonium:

The remainder of regular time, and the extra-time periods as well, were marked by goalkeeper heroics. First, in the 87th minute, Donnarumma, who had already exhibited his world-class talent with a lead-preserving wondersave in the 72nd minute, was once again called upon, this time to keep Italy alive to fight into extra time. He delivered.

Extra time was Donnarumma's counterpart's time to shine. There, Vasilj pulled off a save that was equal parts ridiculous and awkward on a Pio Esposito point-blank header that kept his nation of 3 million people alive for a spot in its second World Cup. (Bosnia previously qualified for the 2014 edition of the tournament.)

That would be the last major action before penalties. I'll keep it short, because this was a rout: Bosnia sank of all its spot kicks with aplomb, while two Italians (Esposito and Bryan Cristante) missed theirs. With the shootout score 3-1 in Bosnia's favor, up stepped Esmir Bajraktarevic, a Wisconsin-born winger who came up through the New England Revolution academy before moving to Dutch club PSV last year. Donnarumma dove to the correct side on the 21-year-old's kick, but couldn't get enough purchase on it to keep it out, and Bajraktarevic—whose parents left Bosnia in the early 1990s due to war before immigrating to the United States in 2001 as refugees—secured Bosnia a trip to his native country.

The celebrations in Bosnia reportedly went all night:

On the other side, Italy joins Hungary as the only team to ever make a World Cup final and then not qualify for this super-sized 48-team 2026 tournament, one that seemed tailor-made to gift countries of Italy's pedigree easy qualification. Nothing is certain in UEFA qualifying, though, as Italy has repeatedly proven. This is in fact only the latest embarrassment in what has been 20 years of World Cup humiliation for the Italians. The last kick taken by an Italian in a World Cup knockout match was Fabio Grosso's tournament-winning penalty shootout kick in the 2006 final against France. Since then, Italy has:

• finished fourth in a group with Paraguay, Slovakia, and New Zealand in 2010;
• finished third below Costa Rica and Uruguay in group play in 2014;
• lost 1-0 on aggregate to Sweden in UEFA qualifier playoffs in 2018;
• lost 1-0 in a one-leg UEFA qualifier playoff against North Macedonia in 2022;
• and lost a penalty shootout to Bosnia and Herzegovina in UEFA qualifier playoffs in 2026.

It's bad when the only positive Italy can point to, since before the iPhone existed, is that it finished above England in a group where neither team advanced back in 2014.

There are plenty of reasons why Italy has fallen off of a World Cup cliff, even as it (rightfully and deservedly) won the Euros in 2021. Italy as a country has stopped producing truly world-class players, save for Donnarumma (who was excellent on Tuesday) and Bastoni (who lost his damn head), in part due to stagnant youth development and the generally middling quality of Serie A compared to its ostensible peers in Europe. The managerial appointments made by the Italian federation have failed to coalesce the talent Italy does have into a team that plays up to its own level. And Italy does not have enough talent or tactical acumen these days to overcome a player as good and experienced as Bastoni making such a massive mistake.

So now, for the third straight time, Italy will watch the World Cup from home. It's darkly funny that, had it qualified, Italy would have immediately become the favorites to win Group B in the tournament proper, which consists now of partial host Canada, Qatar, Switzerland, and Bosnia. This was Italy's best chance not just to make it back to the World Cup, but even to make it back to the knockout rounds, the promised land that delivered the Azzurri its fourth trophy 20 years ago. Instead, a different fourth will be looming large ahead of the World Cup's 100-year anniversary in 2030: Will Italy, one of the most important forces in international soccer history, finally fix what has ailed it in qualifying, or will such a momentous World Cup once again carry on without the country that has won the second-most titles in tournament history?