He attended the Jesuit college at Medina, and excelled in theology and philosophy.
In 1563, he joined the Carmelite Order and took the name “John of St. Matthias.”
He was ordained into the priesthood in 1567. While celebrating his first Mass, he met St. Teresa of Avila and was asked to follow her.
In November 1568, John founded the Disclaced Carmelites and changed his name to John of the Cross.
In 1572, he traveled to Avila to see Teresa and became her spiritual director and confessor. While there, he had a vision of the Crucified Christ and made his now-famous drawing, Christ “from above.”
In 1577, John was ordered to leave the monastery in Avila, due to a growing rift within the Carmelite Order. However, his work to reform the order was already approved, so he chose to stay.
Later that year, a group of Carmelites kidnapped John. They placed him on trial for disobedience, and he was punished with imprisonment.
His cell was so small he could barely lie on the floor. He was barely fed, publicly lashed, and his only luxuries were a prayer book and an oil lamp. To pass the time, he wrote poems. After nine months, he managed to escape.
John spent the rest of his life traveling and establishing new houses across Spain.
He died on December 14, 1591, from a skin condition that resulted in an infection.
Saint John of the Cross was beatified by Pope Clement X in 1675, and Canonized by Pope Benedict XIII in 1726. He is recognized as one of the Doctors of the Church and is the patron saint of Contemplatives, mystics, and Spanish poets. His feast day is celebrated on December 14.
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More on St. John of the Cross: http://www.catholic.org/saints/saint.php?saint_id=65