Many of us indulge in virtual history: the endless fascination of what would have happened if – Hitler had been assassinated in 1935; or Churchill killed at Omdurman; and so on. In literature, meanwhile, most of us enjoy page-turners: books which fill their readers with the desire to pursue the excitement.

But there is another sort of page-turner whose readers can never be gratified – a literary equivalent of virtual history. Even once the pages run out, we are unsatisfied. We want to know what fate has in store for certain characters.

There are at least two good examples in Shakespeare. The first concerns Vienna, and Measure for Measure. The play ends after one of the most moving passages in all literature. Isabella believes that the Duke of Vienna’s Deputy, Angelo, is a monstrous hypocrite who has arranged her brother Claudio’s death. The Duke has sentenced Angelo to a well-earned journey to the scaffold. But the Deputy’s spurned fiancée, Mariana of the Moated Grange, begs the Duke to spare him. She also implores Isabella to join her plea. The Duke expresses incredulity at the request: this is the man who had her brother killed. There is then a stillness, as if the heavens were suspended in their motions. A great actress would hold the pause until it was painful… more pain… before falling on her knees and joining Mariana to ask for mercy.

Within a few moments, everything is resolved. Claudio had not actually been put to death. Angelo is pardoned, and the Duke marries Isabella. All’s well that ends well, as it were.

But what about the next day? Angelo, conscientious as always despite his faults, turns up for duty in the courtroom. The clerk, keeping his voice in neutral, informs him that the trials all involve the latest malefactors swept up in the Duke’s drive to clean up the stews. The wickedest of them all, Lucio, has legged it out of town (thank God for that, Angelo thinks to himself). But there is a brothel-keeper, a pandar and two whores. Angelo decides that it is time to persuade the Duke to reassign him.

For the ideal way of doing that, we could commit a monstrous anachronism and move two Centuries onward. We are still in Vienna, but now Mozartian Vienna, among the cast of Figaro. Count Almaviva is about to go to London as Ambassador. A job-swap would be the perfect solution for Angelo. One suspects, however, that the Count would not agree.  

The second instance involves a move to Venice, indeed, to The Merchant of Venice, and to one of the most enchanting female characters in all of literature. Portia ranks high in the canon with Rosalind and Elizabeth Bennet: to know them is to love them (one could also mention Athena – but loving her would be more complex, and more perilous). We first encounter Portia in her well-named house, Belmont, a palace of enchantments. But there is a drawback to all this affluence designed for pleasure. We learn that she may neither marry ‘who I would, nor refuse who I dislike’. Her late father, a hugely rich man who distrusted the hot-blooded impetuosity of the young, designed three caskets. The suitor who chooses the right one wins fortune and fair lady. Father was obviously a harsh old so-and-so. Although it is not quite as bad as the fate of Turandot’s failed aspirants, the losing gentlemen must swear to eschew matrimony. The more unsuitable candidates, including a Scotsman, are quickly brushed aside. Then comes Bassanio.

There is an irony. Bassanio is exactly the sort of young fellow whom a strict father would distrust. We have all met Bassanios: captain of the Eleven at their public school, good-looking, oodles of charm, they find it easy to command the admiration of females (and males: viz Antonio). They find it equally easy to believe that the world is designed for their pleasure, and to luxuriate in entitlement and self-indulgence: imagine a second-rate Boris Johnson.

Bassanio hears about the heiress Portia, borrows three thousand ducats from Antonio to equip himself with bella figura, sets off for Belmont, and chooses the right casket. She is delighted, relieved and generous. Until ‘now I was the lord of this fair mansion, master of my servants, Queen o’er myself.’ In future, everything will be Bassanio’s, subject to his holding on to a ring of betrothal.

Then the drama begins. Antonio had to raise the ducats he lent to Bassanio from Shylock, the parsimonious Jew. The bond: a pound of flesh. But Antonio’s argosies miscarry. He is at Shylock’s mercy. There is no mercy. Portia, disguised as a lawyer, tries to appeal to Shylock’s better nature. There is no better nature. He wants revenge, and one can understand why: The Venetians are an unattractive lot, who have often insulted him. Antonio went so far as to spit on his gabardine.

Portia excepted, Shylock is the only impressive character in the play. He has a ruined majesty, like an oak-tree whose acorn fell in stony soil. Instead of growing straight and stately, it has struggled upwards, warped and gnarled. But it was the Venetians who created the stony soil. In the great exchange between Portia and Shylock, it might be tempting to suggest that at one or two moments he almost weakens in his bloody resolve. But no, he stands by the law – and gets it.

Then there is general rejoicing. Portia leaves, discards her lawyer’s disguise and is reunited with Bassanio. But he has given away the ring, to Portia disguised as the lawyer, who would accept no other fee. There is a delicious scene when Portia makes game with him and proves yet again how clever she is and how witty. But will that all be wasted on the unworthy Bassanio?

There are two possible outcomes, and as in other works, the ring is crucial. Should Bassanio be forgiven for parting with it in a moment of understandable generosity? Or was it a sacred trust? Portia might succeed in training this unformed cub and making him into a proper man, a worthwhile husband and father. Or she might fail.

It is easy to imagine his arriving from Venice with a boatload of thirsty and roistering boon-companions, who have come for the weekend but are still there three weeks later, debauching her maids, draining her father’s wine-cellar – not to mention his treasury. There could be recurrent exchanges with her steward. ‘My lady, the Lord Bassanio has asked for another three thousand ducats.’ ‘But of course’, she replies with a brave face: ‘My Lord must have what he wants.’ Behind the stoical visage, is she wondering: ‘My father’s wealth was beyond the dreams of avarice. Is it beyond the extravagance of my husband?’ She was Queen formerly – has she now abdicated her throne to a rake and a wastrel? Almost her first words in the Play are: ‘My little body is aweary of this great world.’ Would Bassanio have led her to the despair that follows on from weariness?

It is an appalling thought. It almost calls for a movement, to free the Belmont One. Lorenzo, perhaps the most attractive Venetian character, has lured away Shylock’s daughter Jessica, plus a considerable quantity of gold coins. They take refuge at Belmont. In one of the house’s enchanting groves, lost in each other, they cite previous love partnerships: ‘on such a night.’ But from Dido onwards, they all ended in grief. Is Shakespeare sending us a signal? It is certainly a poor omen for the romantic unions which end the play, including that of Bassanio and Portia.

All hope is not lost, of course. As Shylock discovered, it is never wise to underestimate Portia. But if there were a heaven, not least among the many questions we might wish to ask, there would be one for Shakespeare. How did things work out between Portia and Bassanio?