Pepper was so valuable that it was often used as collateral or even currency. The taste for pepper (or the appreciation of its monetary value) was passed on to those who would see Rome fall. It is said that Alaric the Visigoth and Attila the Hun each demanded from Rome a ransom of more than a ton of pepper when they besieged the city in 5th century. After the fall of Rome, others took over the middle legs of the spice trade, first the Persians and then the Arabs; Innes Miller cites the account of Cosmas Indicopleustes, who travelled east to India, as proof that "pepper was still being exported from India in the sixth century".^[12] By the end of the Dark Ages, the central portions of the spice trade were firmly under Islamic control. Once into the Mediterranean, the trade was largely monopolised by Italian powers, especially Venice and Genoa. The rise of these city-states was funded in large part by the spice trade.

A riddle authored by Saint Aldhelm, a 7th-century Bishop of Sherborne, sheds some light on black pepper's role in England at that time:

I am black on the outside, clad in a wrinkled cover,

Yet within I bear a burning marrow.

I season delicacies, the banquets of kings, and the luxuries of the table,

Both the sauces and the tenderized meats of the kitchen.

But you will find in me no quality of any worth,

Unless your bowels have been rattled by my gleaming marrow.^[13]

It is commonly believed that during the Middle Ages, pepper was used to conceal the taste of partially rotten meat. There is no evidence to support this claim, and historians view it as highly unlikely: in the Middle Ages, pepper was a luxury item, affordable only to the wealthy, who certainly had unspoiled meat available as well.^[14] Similarly, the belief that pepper was widely used as a preservative is questionable: it is true that piperine, the compound that gives pepper its spiciness, has some antimicrobial properties, but at the concentrations present when pepper is used as a spice, the effect is small.^[15] Salt is a much more effective preservative, and salt-cured meats were common fare, especially in winter. However, pepper and other spices probably did play a role in improving the taste of long-preserved meats.

Its exorbitant price during the Middle Ages — and the monopoly on the trade held by Italy — was one of the inducements which led the Portuguese to seek a sea route to India. In 1498, Vasco da Gama became the first European to reach India by sea; asked by Arabs in Calicut (who spoke Spanish and Italian) why they had come, his representative replied, "we seek Christians and spices." Though this first trip to India by way of the southern tip of Africa was only a modest success, the Portuguese quickly returned in greater numbers and used their superior naval firepower to eventually gain complete control of trade on the Arabian sea. This was the start of the first European empire in Asia, given additional legitimacy (at least from a European perspective) by the 1494 Treaty of Tordesillas, which granted Portugal exclusive rights to the half of the world where black pepper originated.