Most players new to online poker start out at the play-money tables before firing away in real games.

Poker icon Barry Greenstein, however – who once played a near $1m coin flip on High Stakes Poker – has gone the other way around.

Still locked out of legal online poker in California, Greenstein converted to play-money poker to fulfill his contractual obligations with PokerStars.

Along the way he inadvertently ended up one of the biggest winners in high-buy-in play-money tournaments ever.

How did the former “Robin Hood of Poker” make the adjustment from playing for millions to playing for pride? We caught up with him at the 2016 PCA to find out.

Barry Greenstein: Robin Hood of Poker

PokerListings: How come you’re now a high roller in play money?

Barry Greenstein: I don’t know if I want to tell you the truth, but I probably will because I can’t help myself. As you know I can’t play poker for real money online because I live in the United States.

So PokerStars asked me to play at least some play money, maybe 3-5 hours a week. You’d be surprised how serious some people take play-money games. They might not be as good as real-money players, but they are good.

One difference is that you can often check the nuts on the river and players would over-shove to try and bluff you, which is something they also do at small stakes.

So, I started playing in play-money tournaments and I played the one with a 1m buy-in, which corresponds roughly to $5 if you wanted to buy that much play money.

I also started to play the Sunday Billion, which is the play-money equivalent of the Sunday Million except player fields are about 800 to 900 players. And before you know it, I won one, and only a couple of weeks later I won it again.

There was an article in the poker media where they said how impressed they were that I took play money so seriously. The truth was I didn’t want to play play-money cash games so I needed something to fill these 3-5 hours PokerStars wanted.

My drive to take it seriously was simply to last long enough; it wasn’t altruistic, it wasn’t my great discipline, it was more laziness, really.

But then what happens if you last long enough in a tournament you want to reach the final table. And within a relatively short time I had two wins and two seconds.

Had I done this in the Sunday Million I would probably be credited to be one of the best online players of all time.

If you’re competitive you want to win, and I’m honestly still upset about the two times where I came second.

Then I played in a 1bn dollar buy-in tournament and in the end it came down to Chris Moneymaker and me heads-up.

He was playing better than me but it came down to a coin flip which I won.

I outlucked him in this heads-up but the thing is, no matter what they say, there is nothing more valuable in poker than having the better hand, especially in the last hand.

PL: It’s interesting that Moneymaker is in these events, too.

BG: I assume he does it for the same reasons as he lives in the United States, too.

I’d have to go to Mexico or Canada to play online for real money, but I can play live in my clubs in Los Angeles so I don’t have a reason to go.

Also, I was overall a losing player online so I don’t have a great incentive to go.

It’s different for many young players because that’s how they earn a living, but there’s no question that I’m a much better poker player live than online.

PL: Has your opinion on play-money poker changed since you started playing yourself?

BG: No, I don’t think so. The only thing is that people enjoy it just as much as the real-money players. But if the Sunday Million comes back to the United States I will be back playing that one.

I can say though that in general, just as in real-money poker, the more you move up the stakes the better the players become.

The biggest difference between the two is that the play-money players are nicer to each other.

They might sometimes call each other names and say ‘how could you make such a bad play’ when they get knocked out.

So they sometimes get upset, but mostly they’re friendly to each other and they’re just having a good time.

PL: Are play-money players better than you thought?

BG: Yes. The benefit for me is that it keeps my game fresh.

I don’t get to play No-Limit live because that’s not my game in the casinos where I play, but playing these big online tournaments every week makes me think about hands just like the way I’d think about real-money hands.

It really doesn’t hurt. And if I look back on my career, No-Limit Hold’em should have been one of my best games.

But for years the WSOP Main Event was the only tournament I played over the year and I played badly because I was simply lacking practice.

I then started playing WPT events and some smaller events at the Bellagio simply to get more practice under my hands and now I can do that online in high-buy-in play-money events.