220, Lot: 552. Estimate $100. Sold for $86. This amount does not include the buyer’s fee.

BULGARIA, Second Empire. Ivan Aleksandar. 1331–1371. AR Grosh (21mm, 1.27 g, 7h). Christ standing facing before seat, raising hands in benediction, IC XC and monograms across field / Ivan Aleksandar and Mihail Asen IV standing facing, each holding cross-tipped scepter, holding Christogram-tipped staff between them; monograms across field; stars flanking base of staff. Raduchev & Zhekov Type 1.13.3-6; Youroukova & Penchev 74-80. VF.

The nephew of Mihail III Asen, Ivan Aleksander became emperor in 1331, following a coup which drove out the rightful though ineffective ruler, Ivan Stefan. The new ruler set about consolidating his position by regaining territories recently lost to the Byzantine Empire. In 1331 Ivan Aleksander campaigned around Adrianople and reconquered northeastern Thrace. After defeating the Byzantines at Rusokastro, a peace was struck, essentially reestablishing the status quo between the two powers, and an alliance was made with the betrothal of Ivan’s eldest son, Michael Asen IV, to Andronicus’ daughter Maria (Eirene), the marriage eventually taking place in 1339. To safeguard his throne in the meantime, Ivan installed his eldest son, Michael Asen IV, as co-emperor in about 1332; he followed this up with the coronation of his younger sons, Ivan Sracimir and Ivan Asen IV, in 1337. It was possibly the intention of Ivan Aleksander that these younger co-emperors could establish immediate control over important cities and regions, and administer them directly.

Throughout the 1340s, relations with the Byzantine Empire and Serbia were periodically strained. Attempts to repel the Ottomans repeatedly failed, and Ivan Aleksander's third son and co-emperor, Ivan Asen IV, was killed in battle against them in 1349, as also happened to his older brother Michael Asen IV in 1355 or a little earlier. A new and more successful attempt against the Ottomans was made in 1355, this time by John V Palaiologos. Although Ivan Aleksander's daughter Keraca Marija was married to the future Andronicus IV Palaiologos as part of the arrangement, the alliance failed to produce concrete results.

To continue his policy of having sons as co-emperors and to replace those who had died, Ivan Aleksander divorced his first wife, and married a second time. The sons of this new union were crowned as co-emperors, Ivan Šišman in about 1356 and Ivan Asen V by 1359. However, Ivan Aleksander's long-range plans had failed as the last surviving son from his first marriage, the co-emperor Ivan Sracimir, became effectively an independent ruler in 1356.

In 1364, hostilities yet again broke out between the Bulgarians and Byzantines. Ivan Aleksander was forced to sue for peace. The relatively successful resolution of the crisis in the northwest did nothing to help recover the losses in the southeast. The Ottomans under Murad I conquered Adrianople and Plovdiv. Preparing to meet them, Ivan Aleksander died on 17 February 1371.