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In the 1960s, game theorists working on nuclear weapons strategy formalized common-sense notions of strategy secrecy and unpredictability, which Trump has embraced. Trump is correct that providing enemies with precise information about deployment timeframes, and committing to a strategy regardless of how circumstances may change does marginally weaken the US's bargaining position relative to its enemies. But like any casual application of game theory, it doesn't tell the whole story.
For one, our enemies (in this case ISIS) aren't the only players in the game. Publicly committing to a military strategy demonstrates credibility by establishing a domestic political cost to breaking the promise, and is a classic case of the 'weakness is strength' idea. By announcing a pull-out date in Iraq, for example, the US sent a signal to other actors, such as local military, that the US's strategic flexibility is constrained. This shifts incentives for those other actors, focusing their priorities or timeframes regarding security autonomy.
Similarly for the norm of predictability, our allies and enemies around the world are less likely to engage in negative-sum defensive escalation if they can reasonably count on the US to not be erratic or crazy regarding military decisions. The US's unparallelled military status and influence places a uniquely high weight on these sorts of systemic, 'stability' effects.
It's plausible--though not guaranteed--that these sorts of benefits outweigh any one-on-one advantages that US transparency and predictability confers on ISIS. This is probably the position of Clinton and the Obama administration, as well as most of the foreign policy establishment. Trump has obviously reached a different conclusion, but is unlikely to have even considered these types of questions and tradeoffs.
Democracies at War
But transparency and predictability in military strategy are good ideas for another reason, unrelated to the game theory cost-benefit calculations: when it comes to military deployment, democratic accountability is fundamentally important.
Quibbling with the military disadvantages of political transparency almost misses the point. Overseas military deployment is one of the most sensitive and morally consequential topics in our democracy, and the notion that a presidential candidate would refuse to discuss it reveals a troubling disregard for the norms and institutions that keep our democracy humming.
If there's any shred of truth to the theory that elections represent in some flawed way an affirmative decision by the 'will of the people', then secrecy over such high-level strategic questions as 'will we decrease our propensity to commit forces overseas, or radically increase it with a policy of extractive neo-colonialism?' is patently absurd. Of course at some level greater transparency becomes counterproductive; we wouldn't want continuous disclosure or direct democracy in the realm of daily flight operations, for example. But the opposite extreme--total secrecy--is equally unworkable.
Democratic accountability doesn't stop at the water's edge, and establishing a precedent that it's okay to place military strategy off-limits to electoral politics is terrifying. US presidents already have tremendous scope and authority to act without democratic constraint, and the implicit vision Trump presents--retrospective evaluation instead of prospective--is not likely to be a sustainable one.
Returning to a cost-benefit perspective, maintaining a thriving and accountable democracy increases military effectiveness over the long-run, and outweighs by leaps and bounds any small strategic benefits to be gained from extreme secrecy. Democracies almost always win the wars they fight, in part because of higher-quality soldiers, but also because they tend to choose their engagements wisely. Trump's policies regarding strategic secrecy directly undermine this second advantage which the US enjoys.