Raymond was deeply religious, and wished to die in the Holy Land, and so when the call was raised for the
First Crusade, he was one of the first to
take the cross. He is sometimes called "the one-eyed" (
monoculus in Latin) after a rumour that he had lost an eye in a scuffle with the doorkeeper of the
Church of the Holy Sepulchre during an earlier pilgrimage to Jerusalem. The oldest and the richest of the crusaders, Raymond left Toulouse at the end of October 1096, with a
large army and company that included his wife
Elvira of Castile, his infant son (who would die on the journey) and
Adhemar, bishop of Le Puy, the
papal legate. He ignored requests by his niece, Philippa (the rightful heiress to Toulouse) to grant the rule of Toulouse to her in his stead; instead, he left Bertrand, his eldest son, to govern. According to
Raymond of Aguilers's
Historia Francorum qui ceperunt Iherusalem, after Raymond's forces took the route through the Alps and Northern Italy, they reached
Sclavonia (
Kingdom of Croatia) in winter of 1096. Described in biblical terms, for some 40 days passed through the mountains, forests and fog without trade and guide from native population who also attacked army's rear (at the time was a succession crisis in Croatia). To discourage their attacks, he ordered mutilation of six captive Slavs, and
Peter Tudebode in
Historia de Hierosolymitano itinere wrote that Raymond "lost many noble knights while passing through
Sclavonia". After "strenuous passage across Sclavonia", they entered
Shkodër the capital of the kingdom of
Duklja where Raymond "affirmed brotherhood and bestowed many gifts upon the king of the Slavs" (
Constantine Bodin), but once again were attacked by the Slavs. Then they marched to
Dyrrhachium, and then east to
Constantinople along the same route used by
Bohemond of Taranto. Along the route they confronted
Pecheneg and Byzantine mercenaries, capturing cities of Roussa and
Rodosto. At the end of April 1097, he was the only crusade leader not to swear an oath of fealty to
Byzantine emperor Alexios I Komnenos. Instead, Raymond swore an oath of friendship, and offered his support against Bohemond, mutual enemy of both Raymond and Alexios. This oath was taken, according to Jonathan Riley-Smith, due to "extreme pressure from other crusade leaders, as well as emperor Alexios". Due to the dualistic nature of the oaths Alexios demanded, one which promised to return former imperial lands to Byzantium and the second of which was an oath of homage and fealty, Raymond most likely found issues with the latter part of the oaths rather than the oath of returning imperial lands. This was because Raymond saw that the oath of fealty conflicted with his crusading vow to serve God. However, according to Riley-Smith, "[d]espite his attitudes toward the oath-taking, after the crusade, Raymond returned to Constantinople and became a strong imperial ally". He was present at the
siege of Nicaea and the
Battle of Dorylaeum in 1097, but his first major role came in October 1097 at the
siege of Antioch. The crusaders heard a rumour that
Antioch had been deserted by the
Seljuk Turks, so Raymond sent his army ahead to occupy it, offending Bohemond of Taranto who wanted the city for himself. The city was, however, still occupied, and was taken by the crusaders only after a difficult siege in June 1098. Raymond took the
palatium Cassiani (the palace of emir
Yaghi-Siyan) and the tower over the Bridge Gate. He was ill during the second siege of Antioch by
Kerbogha which culminated in a controversial rediscovery of the
Holy Lance by a
monk named
Peter Bartholomew. The "miracle" raised the morale of the crusaders, and to their surprise they were able to rout Kerbogha outside Antioch. The Lance itself became a valuable relic among Raymond's followers, despite Adhemar of Le Puy's skepticism and Bohemond's disbelief and occasional mockery. Raymond also refused to relinquish his control of the city to Bohemond, reminding Bohemond that he was obligated to return Antioch to the court of Emperor Alexios, as he had sworn to do. A struggle then arose between Raymond's supporters and the supporters of Bohemond, partly over the genuineness of the Lance, but mostly over the possession of Antioch. ==Extending his territorial reach==