The brother of Michael Comnenus, Theodore's entry into regional politics actually began in the court of Theodore Lascaris, emperor in Nicaea. It was under him that Theodore was first given office and recognition. Had Michael not asked him to come to Epirus in 1215 he might well have served Lascaris rather than become his eventual rival. Instead, he was informed of Michael's assassination and given command of the despotate. Soon after this he almost stumbled on the fortunate (for him) ambushing of the imperial procession of Peter of Courteney. Peter had just been crowned the new Latin emperor by the Pope in Rome and was making his way to Constantinople when he was captured by Theodore and imprisoned (and possibly killed too). The ensuing distress that this caused in Constantinople made it an opportune moment for Theodore to take advantage of the momentum while the hated occupiers remained leaderless. With an impromptu army he successfully laid siege to Thessalonica and the city's defenders surrendered in due time. After the liberation of Thessalonica he saw it as a distinct possibility that he might go on to recapture Constantinople as well. He had himself proclaimed emperor (ignoring the emperor in Nicaea) and planned for the big day.
But he had taken a bigger bite than he could chew. He realized that in order to have a hope of regaining Constantinople he would first need to unseat John Asen, the Bulgar king, because he had proven to be an unreliable gold digger. If he were to regain Constantinople, he figured, it would probably be at great cost in life and expense. This would only have been a tempting invitation for Asen to attempt his own takeover of Constantinople. So, although risky, he needed to take out the Bulgars first to eliminate their future threat. But Asen's army proved to be too much for his own. Theodore just wasn't strong enough yet. After a brief but decisive battle he was captured, imprisoned and eventually blinded. He would, rather surprisingly, continue to play a significant role several years later.
SB 2158 AR Trachy Obv: Christ seated, facing, raising hand and holding book of Gospels.
Rev: Theodore and St. Demetrius standing facing, together holding cross within circle surmounting triangular decoration on long shaft.
SB 2167, DOC IV 9 Billon Trachy Obv: St. Demetrius seated facing, holding sword across legs.
Rev: Half-length figures of Theodore and Madonna facing, supporting patriarchal cross emanating from globe between them; Manus Dei in upper field. 1225-1230 (Thessalonica). $470 4/1/01.