Know When To Hold ‘Em, Know When To Log Off

How to wager on the Internet.

Hurry! Don’t miss your big chance to lose your wife and car in a game of craps. Bills are afoot in the House and Senate to outlaw online gambling before it really takes root. Though rapidly changing technology and the freebooters who run offshore casinos will likely stymie any new legislation, that won’t stop the feds from trying. So, if you’re interested in online gaming and/or wanton self-destruction, deal yourself in before it’s too late.

Or watch me instead. I don’t have a ton of gamble in me, as the Vegas phrase goes, but I have a very soft spot for a challenging game of poker. I also imagine that I know a lot about sports, and I enjoy controlled risk-taking. In short, your average, fairly well-informed sucker. So come along, as I demonstrate how to lose scads of money in four easy steps, without leaving my desk chair or deriving any sort of tangible return.

Step 1:

With at least 600 gambling sites on the Web and new ones launching every day, it’s tough to decide where to burn your cash. (Online gambling is banned on a state-by-state basis, so check with your local cops before taking the plunge.) No comprehensive guide to online gaming exists, and the sites that publish casino reviews take ads from those same casinos. Consumer Reports, where are you?

I happen upon Showgirls Casino, which, unlike many other sites 1) requires no software download to play its games, and 2) posts its odds (97.8 percent payback on slots, which is great–the average slot payout on the Vegas strip is 95.7 percent). In the standard routine, Showgirls has you deposit funds with a separate e-commerce outfit; then you draw on that account to buy virtual chips at the casino. Tapping the $500 I started with, I set up a $150 account with my credit card. Once I started, there isn’t much difference from a real casino. Pros: No destitute hustlers lurking about (unless you count my friends), and I didn’t have to leave the house. Cons: No cocktail waitresses, and a Java applet is no competition for a blackjack table’s perfect green felt. It’s a trade-off–you may love the privacy and convenience, you may miss the ambience.

Showgirls (based in the Dominican Republic) offers all the usual games–craps, roulette, etc. I immediately lose $40 in video poker (if you play, learn the strategy). Then I lose $15 in roulette and another $15 on the slots. Bam–down 70 clams in 20 minutes. Click, click, broke. How quick and painless money-losing can be when it’s all just numbers on a screen. A session of blackjack gouges $50 more (counting cards is useless here as the deck reshuffles after every hand). After an hour, I staunch the bleeding and ask them to mail me my remaining 30 beans. The site promises a check in a few weeks.

Net so far: -$120.

Step 2:

Most online casinos offer the same games and the same software. Slotland distinguishes itself with the lowest-budget design on the Web. Also, it posts no odds. I buy in for $25 and get a $10 first-time bonus for registering (most sites do this). After losing $7 on the slots, I withdraw my whole account–at a $3 profit! Then I go back in and deposit another $25, only to double my money on a single pull. (By the way, on wins of 75 cents or more, Slotland offers a link to a cheesy erotic photo.) For bare-bones gaming, this place will do the trick.

Net so far: -$92, though I’m still waiting for the Slotland check, too.

Step 3:

Because sports betting is illegal everywhere but Nevada, I predict that online sports betting will become big. My friend Andy Glazer, a pro gambling expert, says some sites cancel your sports bets if they think you’re too good or if they figure out that you gamble for a living. (Many online sites just plain stiff their clients for no reason.) Andy’s advice: If you must wager on sports, go to Vegas or stick with your neighborhood bookie–he’s probably more reputable, if more clearly illegal. If you do go online, use an Australian site, as they’re the best regulated.

Throwing caution to the wind, I try i-Sportsbook from Antigua, because it provides the easiest interface for my credit card deposit. I put $75 on the New England Patriots as a 2.5-point underdog and $50 on a Boston Red Sox playoff game against the Cleveland Indians. I win both bets, scoring 125 samoleans. My Pats lose but cover the spread (they only lost by 2, and the odds-makers spotted them 2.5 points). My beloved Sox beat the Indians. Within a few days, i-Sportsbook refunds my credit card deposit, as promised, and a week later I get a check for my winnings. Quite straightforward and trustworthy, but I was making miniscule, unthreatening bets.

Sports aren’t the only events to bet on at these sites. One offers George W. 6-to-5 odds to win the White House (bet $5 and, if you win, get back that fiver plus an additional $6). Al Gore is 9-5 to win, and Bill Bradley is 7-2 (bet $2 to win $7). You can also bet on the outcome of the Microsoft trial, or whether Leonardo DiCaprio will OD before Sept. 1, 2000.

Net so far: $32 in the black!

Step 4, in which unfortunate things happen:

Your best bet in any casino is at the poker tables–real poker, not video poker–because you play a game of skill against shmoes like yourself, not a game of mathematical chance against a machine or a deck of cards. The more poker skill you acquire, the better your odds. At a meatspace casino or a virtual one, the house makes its money by taking a small percentage rake from each poker pot, or renting the seats by the hour. There aren’t a lot of live poker games on the Web, but unhappily, I found one.

All the live poker sites I visited–,,–require a download of the same software. I decide on because Mike Caro, a pro poker player whom I’ve met and like, endorses it. I put $150 in my account with ease, but when I try to play I get an error message about being unable to link up with the Planet Poker server. This error message appears on a few different computers hooked up to a few different corporate networks that I try, making me think that the network administrators have configured their “firewalls” to disable these games. I succeed in connecting to when I borrow a friend’s laptop and connect through his Internet service provider.

Once in the poker room, you scan the virtual tables for empty seats, and click to sit down or to join the waiting list. After a 45-minute wait, I still can’t find a chair for the low-stakes Texas Hold ‘Em game ($3 and $6 bets, pots around $30 or so). Impatient, I jump into a higher-stakes game ($5 and $10 bets, pots more like $100), which turns out to be a horrible idea. These players are much better than the low-stakes players and take my money in a hurry. The playing interface is smooth and simple, popping up your options to fold, call, or raise when it’s your turn. But not only does my Web connection fail in the middle of one hand (if this happens, the game assumes you have called the bet, then kicks you off the table when the hand ends), I flat get beat when I risk any chips. Players with handles like “nineball” and “fatso” just outplay me. On one tough hand that lost me $60, I was pretty confident with my three jacks–only to see “sleepy” make a gutshot straight on the last card to whup my trips and steal my chips. I lose $150 worth in under an hour, but I love the challenge. Of all the online games, this is the one I could get frighteningly into. (Though in the future I’ll stick with the low-stakes games.)

The drawbacks of live online poker? You can’t read bluffs in your opponents’ trembling fingers and bobbing Adam’s apples. The only guaranteed way to get a bead on players is to watch for betting patterns to emerge. Another thing about these games that makes me nervous is that two players in cahoots at adjacent computers could rig the table, playing in tandem and driving up the bets when they know they’ve got the hand won. Finally, it’s hard to gauge the competition. With the online anonymity, for all I know I was playing against Phil Hellmuth Jr. But the game seemed fair, and I was simply overmatched.

Final net: -$118, though I’m still waiting on the Showgirls check, and as for the Slotland check, no, yesterday’s e-mail confirmation of my withdrawal did not convince me that it’s actually on the way.


Online gambling is here, probably to stay, and it’s going to be unfathomably big. If you think video poker at airports is ” convenience gambling,” wait till you see co-workers feed their paychecks into online slots from their desks. Depending on what kind of person you are, this may mean you should 1) establish an offshore casino in the Antilles before the Department of Justice cracks down, or 2) wait for this stuff to shake itself out before you blow 20 bucks playing Web roulette. As long as Indian casinos are only a few hours away, giving your credit card number to a distant and foreign Internet operation might not be worth the risk. If you do log on, though, perhaps I’ll see you at the virtual Hold ‘Em table. My handle is “seth.”