Military history is not only the story of greatness, of inspired leadership, of singular genius, and masterful campaigns, but also of folly, failure, and disaster. There are plenty of moments throughout history where you just have to wonder, "what the heck were they thinking?"
A new & correct map of the trading part of the West Indies : including the seat of war between Gr. Britain and Spain : likewise the British Empire in America, with the French and Spanish settlements adjacent thereto : adorn'd with prospects of ye most considerable towns, ports, harbours &c. therein contained from the latest & best observations London: Printed for and sold by Henry Overton, at the White Horse without Newgate, 1741
These moments are some of the most endearingly human parts of history (if, also, sadly, some of the most costly in blood and treasure). But their faithful recreation also poses a challenge to the wargame designer. Many times, the designer will have to resort to what are impolitely called "idiot rules", in which a player is required to do some fool thing simply because said fool thing was done by some fool historically. It's why, for example, most games on the Fall of France have some kind of rule in place to prevent the French from effectively protecting against an assault through the Ardennes.
I'm not a huge fan of this, as either a player or a designer. Having to pretend that my opponent's killer stack isn't there because I'm still following a mandatory movement rule for the next two turns isn't my idea of a good time. On the other side of that coin, however, I wouldn't want a game that falls apart, and has no chance of anything approaching the historical outcome, simply because one of the players has the good sense not to conduct himself like an utter loon.
It's a tricky, thorny problem, and I'm not going to pretend that I have the be-all, end-all solution. But there is one approach I found fruitful, and that is to tie historical goals to viable in-game incentives.
For example, during the Battle of Inkerman, one particular area saw an inordinate amount of action. This was the Sandbag Battery, which changed hands between the Russians and the British several times, and was the site of many a charge and a counter-charge. The blood expended over this little fortification was immense, but its actual strategic value was minimal: holding the Sandbag Battery really meant very little in the grand scheme of the larger battle.
"Second Charge of the Guards when they retook the Two-Gun Battery at the Battle of Inkerman, 5th November 1854", 1854, William Simpson
But psychologically it was important for both sides. I represented this in Blood in the Fog by giving the Russians an extra space on their Victory Track at the end of any Game Turn in which they held the Sandbag Battery hex. The Russians need all the help they can get, and so the Sandbag Battery becomes a coveted target. Similarly, the Allies are eager to deny them this advantage, and so you will see the same kind of fierce fighting over this largely insignificant little hex.
It's important that the incentive be viable, however, without being ridiculous. In Supply Lines of the American Revolution: The Northern Theater, 1775-1777: Is This Title Long Enough, I needed to incentivize the Patriot Player to recreate the laughably doomed 1775 invasion of Canada. I tried to do this in the earliest versions of the game by giving the Patriot Player a gigantic number of new/reinforcement Units should they take Quebec. It would be hard to do, but boy, once they did it, they would just have a steam-roller that would run right over the Brits! I thought, this reward is huge enough that the Patriot Player will make a go for it, and also huge enough that the Crown Player will do everything they can to stop them.
March to Valley Forge, 1883, William B. T. Trego
The problem is that players ignored it completely. Because the reward was so outsized, the Patriot Player knew he would be fought tooth-and-nail, and he figured, rightly, that it wouldn't be worth the bother. I can't think of a single game where the Patriot Player ever pulled it off, and the only times they even tried to do so was when I was playing that side (I normally play the Crown side).
The other problem is that the incentive wasn't viable from a historical perspective. Even if the Americans managed to capture Quebec, the chances of the Canadians actually joining the rebels willingly was pie-in-the-sky stuff (another reason why the whole plan was hilariously ill-conceived).
La Citadelle de Quebec. The current fortification is a later improvement on the smaller, wooden citadel built in the mid 18th century. The Citadel remains an active military installation.
In the final version of the game, I scaled back the incentive, while making its effects more meaningful. The Patriot Player gets a step closer to victory if he holds Quebec, which somewhat mirrors the Sandbag Battery dynamic, but, and this is the important bit, he also gets a step closer to victory the first time he attacks Quebec. So, even if capturing Quebec is off the table (it probably is) and perhaps not worth the effort (it probably isn't), trudging up there and making the attack is worth it.
In fact, it's worth doing it as early as possible. The Support Marker which determines Patriot Victory is very easy for the Crown Player to push back in the early game, and will remain so until the Patriot Player is able to establish a "buffer" zone, so to speak. That attack on Quebec can let them do that early on, making it easier to push the Support Marker to the Declaration of Independence, which establishes a minimum level beyond which the marker cannot fall for the remainder of the game.
In both of these cases, players are encouraged to pursue historical goals, even if they might be more than a little boneheaded in hindsight, because the game models historical (if purely psychological) reasoning. Much better, I think, then simply requiring that someone move in this direction for this many turns.