Can he do it on a cold Saturday night in Wellington?
That question could be answered in a couple of months, when the All Whites put their World Cup hopes on the line against South America's fifth-best side at Westpac Stadium.
New Zealand clinched their place in the intercontinental playoff this week. The South American qualification series has two rounds to play.
But right now, sitting fifth and on a collision course with the All Whites is Lionel Messi and Argentina. The question posed to open this piece might soon be asked of a man regarded by some as the greatest footballer of all time.
So with two matches remaining for Argentina to claw their way into one of the continent's four automatic berths - providing New Zealand with what on paper would appear a smaller speed bump on the road to Russia - here's another query: should Kiwis be hoping for A-list opposition or the easier path?
There's no doubt in the mind of this observer but, before we discuss the desirability of a date with Messi, let's examine that so-called easier path.
As it stands in South America, Brazil are the only team whose 2018 ticket has been booked. Second-placed Uruguay, who finish with matches against the group's bottom two teams, are almost safe.
Which leaves Colombia, Peru, Argentina and Chile scrapping for two automatic spots.
And given Argentina (beaten finalists), Colombia (quarter-finalists) and Chile (knocked out by Brazil in the round-of-16) all impressed at the last World Cup, one of those teams are not like the others.
It's true, Peru last featured at the World Cup in 1982 and possess no player of the calibre of Colombia's James Rodriguez or Chile's Alexis Sanchez.
But what's also true is Peru are ranked by Fifa as the world's 15th-best team. And before we justifiably quibble over the merits of that particular list, Peru are ranked 11th by the more mathematically-sound Elo rating system. (New Zealand are 123rd on Fifa and 73rd on Elo.)
The beauty of football, of course, is that rankings matter little over 90 minutes; the All Whites are more aware than most of that axiom. But what about over 180 minutes, when the second half of the tie is played in South America?
Which, if it's Peru, means 80,000 locals barracking for their country to make their first World Cup in 36 years. And the effect of that home advantage seems difficult to overstate, considering that in this qualifying campaign, Peru have lost just two of eight home games (2-0 to Brazil and 4-3 to Chile) while defeating Uruguay and drawing with Argentina.
What I'm saying is that Peru are good at football and, not to sound defeatist, the All Whites are facing mission impossible no matter whom they play. So why not Argentina? Why not be treated to Messi and Sergio Aguero and Angel Di Maria in a competitive match on New Zealand shores?
Such a clash would be an occasion unrivalled in Kiwi sport - when other all-time greats such as Serena Williams and Tiger Woods visited, individual motivation was questionable.
For Argentina, on the other hand, failing to reach the World Cup would be a national disaster.
And, remember, Oceania will from 2026 receive automatic entry to an expanded tournament. Which means, after Qatar 2022, future qualification is essentially guaranteed and will depend on ties against the likes of the Solomon Islands, who boast few footballing geniuses in their ranks.
Can Messi do it on a cold night in Wellington? It's uncertain but, while we still enjoy the privilege, we should all want to see him try.