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In regards to his heritage, the Tolomei family was considered one of the most outstanding families in Siena. Although initially a jurist, Bernardo eventually founded the Olivetan Order, a Benedictine monastic order, in 1313; the Monte Oliveto Maggiore was built in Tuscany as the mother-house of the order.
The monastery owned most of the land in the Siena region, which was overseen by the order's private government. By the time of Bernardo's death, the monastery was left in a lucrative state thanks to his background as a jurist.
- Bernardo took his name out of admiration for Bernard de Clairvaux, a French abbot and notable Templar.