Sports Gambling Strategy: The Art of Tailing Bets

Everyone wants to be the best of the best. And in sports betting, that’s generally associated with becoming the most successful handicapper. Sports gambling media is littered with touts, Discords, coalitions, websites, models, and even dual-talented “experts” in both gambling and showing some skin (also, technically, “models”). But, while the glory often goes to those who find success giving out wagers, the reality is that 99% of people in this space either purely tail others or bet their own plays but don’t give out picks (or something in between).

While you’ll find tons of content and analysis on how to become the best handicapper, very little is written about how to become an expert at tailing bets. Sure, tailing doesnt come with any ego stroking, but learning how to effectively use the gluttony of information and options at your fingertips can make you just as much money as doing the analysis yourself, while both saving you time and avoiding the massive stress that comes with being a handicapper.

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And, while it may seem like a simple exercise, the reality is that learning who and how to tail takes a lot of skill. Hell, there are people who I respect purely as gamblers who are great at tailing bets, and even those who do give out picks almost always tail other people sometimes.

So, to keep things simple, here is a list of things to consider when it comes to becoming a top class “tailer” in sports gambling. Each could probably be an article in it’s own right, but I’ll save that wordy nonsense for another day.

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Betting Strategy: How to Tail Bets

Weed the Garden

First thing’s first - there are a million options to choose from and it’s not an easy exercise to figure out which are roses and which are poison ivy. Making that determination is largely both a product of time and personal judgment, but there are certain red flags to look out for. Obvious examples would be people who delete losing bets or accounts who recommend 10+ unit wagers, but a crucial factor to consider is how seriously the source is taking their gambling.

Joking about being a “losing gambler” or saying “this wont hit” when placing a bet is a light-hearted way to take off some pressure, but to be a successful gambler you truly have to hate losing. Look for people who take missed bets personally and seriously.

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Not Just What, but Why

I have very few hard rules when it comes to gambling, but this is one of them; I don’t trust people who won’t explain their reasoning. Any person can place a bet or a parlay, but I want to know why you think that bet is worth placing. Not only does it show me you’ve thought through the decision, it also gives me the ability to agree or disagree.

The “why” can come in a variety of forms - a detailed analytical write up, an expected value return (EV betting), or even just a general thought process - but you need to know there is a reason.

Reputation Matters

Having a big following is a good starting point to figure out who is worth tailing. The logic is obvious - those people have grown because they’ve succeeded, which is a good estimation of future success. But not every big account is worth its following, and many small ones outperform expectations.

I’m not here to list those who meet each category, but a good trick is to see whether people who know their stuff want to associate with that person. Cappers with connections to high quality websites like Dimers.com or big Discords have to be accountable for their work, which shows you that they meet some level of scrutiny, but you can also get insight from less obvious tells like interactions on social media. Be weary of black sheep.

Variety Without Excess

It may not be a surprise, but there are, in fact, STILL too many good handicappers for you to tail all of them. The reality is you cant, and shouldn't, try to tail every good capper you find, and the key is to choose the ones who work best for you.

Variety is still important. You should look to a range of sources to see if there’s any prevailing logic or to see different viewpoints on a bet, but spreading yourself across even three or four handicappers on a given day is too much risk. Learn to use as much of the information as you can, but ultimately you need to limit yourself to a healthy and productive number of bets to succeed.

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Optimize Your Resources

I have a lot of friends with Discords who aren’t going to like this statement that much, but paying for picks is a dangerous game. The margins are already slim in sports gambling, and the monthly output on a Discord or website when there are so many free options is hard to justify (in my opinion).

That said, it may also make a lot of sense based on how you value those services. If you think access to a specific gambler or the vast range of knowledge from a multitude of cappers is worth the marginal price, then it certainly could be useful. But doing so thoughtfully and deliberately is a crucial piece of the puzzle.

Does This Bet Make Sense to You?

Even when you commit yourself to tailing a certain person or strategy, the above question should never leave the back of your mind. As I tell people who tail me all the time, I am CERTAINLY not always right and you should have the final say in whether my logic checks out (after all, you’re risking your own money, not mine).

Trust is still necessary, but blind trust that stops you from thinking critically could put you at risk and prevent you from avoiding mistakes.

Think Long Term

 Gambling is a long term game. As far as tailing goes, that has a couple of implications, both of which are important. The first is to not give up hope on a strategy because of short term losses. Everyone has rough patches, and you need to weather the storm some days. The second, on the other side of the coin, is to not go down with the ship (RIP Titanis Sub). Sometimes it may make sense to move on and get a fresh start, and there’s nothing wrong with that.

The key, though, is to be thinking about those decisions based on how you expect them to play out over months or even years. Chasing profit in the short term can get you into trouble in a variety of ways and, while long term strategies don't always succeed either, they have a much better chance of survival. They didn't build Rome in a day, and you wont build gambling success that way either.