Here’s a cool thought experiment from Joe Posnanski (via the inevitable kottke.org) [NB: I have no idea who John Lovitz is either. But I’m guessing he’s some sort of sport guy]:

So, here’s the game: The Jon Lovitz Devil has consigned you to an eternity of being stuck in traffic in a wheezing Ford Escort without air conditioning, and the only radio station plays Michael Bolton 24 hours a day. But you have one chance to escape your fate. You get to choose one athlete, at his or her peak, and one sport. Ever. And if that athlete wins, you get a whole different eternity, with chocolate-covered strawberries, DirecTV and a deck that overlooks the ocean.

Ah, but there is one catch. You get to pick the athlete and sport. But the Jon Lovitz Devil gets to pick the terms.

It’s basically a clever way of stating the old question “who’s the greatest athlete in any sport,” because it forces you to consider all the possible circumstances under which they might not be the greatest:

I won’t lie … the venue and setup are a big deal. For instance, some people say they would absolutely take Roger Federer in his prime. And that’s great — Federer in his prime is about as good as it gets — but if the JLD chooses Rafa Nadal on the clay at Roland Garos, I wouldn’t feel too confident (or what about McEnroe at the U.S. Open, but both players have to use wood rackets).

This ability to switch eras and opponents is cunning, although it does mitigate in favour of modern athletes, I think, because if one were to pick, say, Rod Laver, the devil could say he’s playing Novak Djokovic circa 2011, on a hard court and with modern raquets. Laver never played with a modern raquet and therefore never had the chance to develop the crazy shots and playing styles that modern tennis players have. So while it’s highly doubtful that Djokovic will achieve the feats that Laver did, I’m fairly sure that if you transplanted Laver in his prime to the present day and threw him on a court with Novak, the result would be ugly (this is of course where the game gets hazy: should Laver-in-his-prime be allowed a year to acclimatise to the modern game and modern coaching? Probably not, under these rules, but that would be hella interesting. To just continue with this theme for a moment: imagine that the current top four were transplanted to the 70s or early 80s and had to play on fast surfaces with wooden raquets. I’d say Federer is the only one of them that would win things: the others just wouldn’t be able to play their shots. Murray, with his adaptability, range of shots and heavy use of slice might fare better than Djokovic and Nadal, but only Federer could be expected to prosper. One more argument in favour of him being the GOAT, I guess).

Another thing that’s tricky is team sports. In the rules,

if you choose Michael Jordan and a 5-on-5 basketball game (as most people would), he cannot say: “OK, well, then I want it to be a three-point shooting contest with Larry Bird.” That’s breaking the rules — the JLD is not allowed to change the fundamental game itself. If you choose Michael Jordan and team basketball, the JLD has to have a basketball game (with each player having four teammates of precisely equal skill).

But it’s a lot more difficult to imagine this scenario: one tends to think of football or other team players in the context of the specific group of teammates that you’ve seen them play with. So if I wanted to pick Cristiano Ronaldo (which I obviously wouldn’t, given his record against Barcelona), I would probably be thinking of him as either a Man Utd or Real Madrid player (ooh interesting question: which team is better: United 07-08, or Madrid now?). But the rules state that he and the one player that the devil picks for the opposition each play with 10 other generic players of equal skill. This scenario is so sterile – no tactics, no opposition strengths or weaknesses, that it becomes impossible to imagine how it might play out. If you pick a great captain like Martin Johnson, how can you assume that he would raise the level his team were playing at if they were all just generic players? Would he have 6 months playing with them beforehand?

So whatever, there’s still plenty of scope to talk about individuals. I think tennis is a minefield and you probably wouldn’t want to go there. Federer, as has been seen, is flawed because of Nadal on clay. Djokovic c. 2011 is very tough, although Federer did beat him at the French and should have beaten him at the US, so I’m not sure you’d want him playing for your eternal soul – plus I don’t rate his or Nadal’s chances against McEnroe in 1981 on grass with wooden raquets. All the old players are disqualified because you could transplant them to the present. In the comment thread on the original piece someone mentioned Steffi Graf 1988 – who had what is actually the sport’s greatest ever year – but she wasn’t facing Navratilova in her prime so tricky. Plus, by that point raquet technology was coming along and her forehand might not have been so devastating in earlier eras.

Pete suggested snooker to me yesterday and I can see that. Hendry circa 1994, 1995 was unstoppable – I don’t think any player since has reached a higher level in matchplay. But the late-90s Ronnie O’Sullivan – if he turned up – would present a hell of a threat,* and Mark Williams was pretty amazing in the early 00s. Then there’s darts, but I don’t really know anything about that.

OK I’m pretty exhausted now. Oh wait, yeah, people are mentioning athletics, and of course there’s Usain Bolt c. 2009 when he ran 9.58 and 19.19. Difficult to bet against over either 100 or 200 metres. Might be another story on a grass or cinder track – but not really. I thought for a moment of Paula Radcliffe in the marathon, she was fantastic, but the Athens Olympics puts paid to that. I also seem to recall a time when Haile Gebrselassie was setting world records at 5 and 10 thousand metres for fun… That could be interesting. Oh and Jonathan Edwards, triple jump, 1995. That Gothenburg performance remains one of the great feats in athletics.

There are a ton of other sports… Jahangir Khan went five years unbeaten in squash, for instance. Could be a good pick.

Do let me know if there’s something obvious I’m missing here. Am obviously not that knowledgeable about golf or US sports or all sorts of other things. I mostly just like talking about tennis.

*Having said that, the one time they did play when both were around their peak was the World Championship semi final of 1999, which Hendry won 17-13. It was one of the greatest matches of all time, with the 21st through 24th frames all won on century breaks, and  eight centuries overall in the match – one of O’Sullivan’s being a failed 147 attempt. I remember when O’Sullivan levelled it at 12-12 with a 110, the commentator saying that the only way the match could possibly get better would be if both players made 147s. Unfortunately the final session proved a bit of a damp squib, with O’Sullivan fading and Hendry tying up the match pretty comfortably. Still.

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