Due to the desperation of the situation, Theodore, alongside John of Natala, was sent to the court of Charles VI of France as an imperial ambassador, bearing a letter from Manuel requesting the French king's military aid.
Further to this, Charles also provided funds for the two nobles to travel to the British Isles to treat with King Richard II of England, with the aim of soliciting further aid.
[4][5] Though the latter was too distracted by domestic troubles at this point to provide any support,[6] Theodore and John were able to return with six hundred French troops led by the Marshal Boucicaut, clearing the immediate approach to Constantinople and breaking the blockade.
[7] In the autumn of 1398, Theodore was named ambassador to Venice, where he maintained both a commercial presence as well as a political one, and was awarded citizenship of the republic by the Doge in December of that year.
[10] He is believed to have had the following issue: The Byzantist Donald Nicol, who initially attributed the offspring to Demetrios Kantakouzenos, later reversed his position and stated that it was more likely that Theodore was the actual father.