John’s father, Gonzalo de Yepes, was of a prominent family in Toledo, Spain. At his marriage to a poor girl, Catherine Alvarez, he was disinherited, and tried his hand at the silk-weaving trade. When Gonzalo died young, Catherine was left destitute with three young sons, John being the youngest.
Sent to a poor school in Medina, John found work at the city’s hospital, and there laboured for seven years.
Already given to the practice of prayer, and to bodily austerities, he studied with the Jesuits. It was revealed to him that he was to serve God in an Order, the ancient perfection of which he would help to renew.
At twenty-one he took the Carmelite habit as John of St. Matthias. Though meaning to be a lay brother, he excelled in theology and was ordained in 1567.
Early on, he obtained permission to follow the original Carmelite rule, without the mitigations allowed by various popes.
When St. Teresa of Avila, the great reformer of Carmel, met John in Medina-del-Campo, she knew he was the man for the reform of the male branch of the order. Though John was small in stature, Teresa sensed his courage and commitment. With all the proper backing and credentials, she and John proceeded to found reformed branches of the Carmelite Order in Duruelo, Pastrana, Mancera and Alcalá. As a reformed Carmelite, John took the name of John of the Cross, indeed a prophetic title.
Around this time in his life, after tasting the joys of contemplation, John entered a period of aridity, scruples, and interior desolation. While assaulted with terrible temptations, he was also persecuted with calumnies. His book, Dark Night of the Soul is the child of these trials. But in the calm that followed the storm, St. John became a great mystic, writer, and is deemed one of the best poets that ever lived.
He later, along with St. Teresa, suffered much by confusions generated within their order, as a result of the reforms. He was imprisoned by his own brothers, as he was pressured to abandon the reform. He also suffered a severe beating at the hands of the Vicar General, which marks he bore until his death. After nine months of incarceration, he managed to escape, and fled to a reformed friary.
In 1579 he became head of the college at Baeza, and in 1581 was chosen prior at Granada. It is around this time that he began the writings on mystical theology that made him a Doctor of the Church.
But troubles within the order followed him. At one point he was stripped of all status and was sent to a remote friary. Another time there was a threat of expulsion of the holy reformer from the order. Ultimately, he died in a friary whose superior was hostile to him though, ultimately, repentant.
But John of the Cross had reached that level of sanctity where crosses were welcomed and gladly embraced in union with his crucified Lord. After suffering acutely for three months, he rendered his sterling soul to God on 14 December 1591.