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In which situations should my opening lead be a trump?

For example, when the opponents have a 4-4 fit, or when I have a singleton etc.?

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Whether you should lead a trump depends on the sort of defense you'll want to execute on the hand. Broadly speaking, there are five lines of defense:

  1. A forcing defense (you force declarer to ruff, making them run out of trumps while the defense still has them). This is a reasonable approach when you or partner hold four trumps, declarer is in a 4-3 fit, or declarer is known to have shortness. Leading a trump here is usually fatal.

  2. A ruffing defense (you want to ruff declarer's winners in a side suit). This is a reasonable approach when you or partner are short in a side suit held by opponents. Usually you'll lead a singleton, or an ace in a suit partner holds a singleton in. Leading a trump is usually fatal.

  3. An active defense (you try to take your side-suit winners before declarer can establish a side suit). Against a trump contract, you may take this approach when dummy has shown a long, strong suit, when opponents have shown extras and tried for (or bid) slam, or when you can see that declarer's second suit is breaking. Leading a trump is usually fatal.

  4. A passive defense (you try to make leads that don't give away tricks). Against a trump contract, you may take this approach when you know or suspect that your tricks are safe, as long as you don't give declarer extra opportunities to finesse, create entries in dummy, etc. Leading a trump here is often safe.

  5. Cutting down ruffs (you try to prevent declarer from ruffing tricks in a side suit). This is often right when the auction indicates opponents are in a misfit, or when you have good cards in trumps, or when dummy has shown shortness in a side suit. Leading a trump here is often required.

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  • 3
    Form of scoring matters. A passive defense that keeps declarer from taking an overtrick is much more attractive at matchpoints (or board-a-match), while taking a gamble that partner has the right high cards or distribution for a ruffing or active defense to set the contract is more attractive at some form of IMP scoring (or rubber). – Alexander Woo Sep 15 '16 at 23:04
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Basically, the time to lead trumps is when you have reason to suspect that your opponents bid their contract on trumps and "distribution," rather than high card points. This is particularly true when your opponents have "sacrificed" to keep your side out of a game.

Another example is when you have 15 points, and your opponents bid three suits, only one of which fit. You can suspect that declarer and dummy are short in each other's side suit, and declarer plans a cross ruff. You lead trumps 1) to make sure that your opponents have to play two trumps on every trick and 2) to protect your high cards, especially tenace holdings like KJxx that you don't want to lead from.

Another example is when an opponent bids a suit, one partner's (takeout) double shows strength in the remaining three suits, and the other passes for penalty with something like AKxxx or QJTxx of declarer's suit.

In essence, you want to "draw" trumps so that your side's high cards will prevail.

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