The best and wisest of friends, Nikeforos Prinkeps Cheilas, is one of the small group of intellectuals of mid-century Mistra, and probably the most enigmatic. Cheilas first appears in 1433, when he gave a monody at the memnosyne for Cleofe. It is an extraordinary work, highly emotional, and full of powerful metaphors, but it is his only surviving writing. A number of letters to him have survived, which collectively give a strikingly detailed portrait of a complicated but valued personality. No letters of his survive. As Eugenikos wrote him in 1455:
Your letters are double treasures, O best of men, winged reminders of your dear countenance and our association, among us even when we have received nothing whatsoever.
It seems that Cheilas left Mistra with Theodoros in 1443 when he became Despot at Selymbria. This put Theodoros in Constantinople most of the time where he intended to pick up the throne from John. In the summer of 1448, John, seriously ill, still had not named an heir. Theodoros had been quarrelling with him over money, and it appears that with the aid of family members and aristocrats in Constantinople, and his entourage, plus the prospects of foreign troops and the promise of a foreign bride, Theodoros was ready to attack Constantinople and seize the throne. But there was a major epidemic of plague, he delayed his attack, contracted plague and died. His body was taken to Constantinople and buried at night in the Pantokrator. His friends and entourage – including Cheilas – sat by the tomb for seven days and nights in the traditional homage, in terror of what might happen to them.
Nothing happened. Too many important people had been involved, and details were covered over, except that everyone knew about it. Cheilas must have written a mound of mea culpas to everyone he had ever corresponded with. Bessarion received one, and responded with generosity in considering why Cheilas might have decided as he did.
You thought you were doing the right thing in deceiving us, having other considerations, and saying what was not the case, but you did not escape us in your attempt to conceal the truth in your concern for loyalty and good will toward our leader and despot, for his sake keeping his secrets truly secret. . . . It is no ordinary virtue for those who consort with dynasts to understand that they must hide the mysteries of those in power . . .Why would one not speak the truth to you and not praise acts worthy of admiration? Why would he not spare a friend from accusations or not supply the defense of one most dear to him. . . . We clearly do not blame you and we have acquitted you of any crimes already. Do not write your defense to us and give no thought to supplication. . . .
For you should view it as I do, that we were harmed by the loss of a brother and a wise friend, while we hoped that you would fare well, for by doing so you would clear away our dismay and comfort us that you were together with better companions. Or, if you willingly endured because you did not accept a division and separation from your benefactor, and were overwhelmed by love, that in itself was the better, and something for which--if you had not felt it--then you might need an apology, such as is not needed now, since you did feel it.
May you be in the midst of all good things, oh best and wisest of friends, and may you overcome all your griefs and, with the support of God, enjoy all the best of the great city. For the present, we wish you to cheer us with the occasion and beauty of your correspondence, and with better words about yourself. In the future, your brilliance will be seen brightly by us who love you. For they are well whenever and wherever your situation is better and pleasanter.
Scholarios was a man of many faces. Without revealing his support of Theodoros, and using language in keeping with his role as a judge, he wrote Cheilas:
Such is your case. We shall not believe you, and forget the evidence of your actions, and we shall not listen to you belittling your state when we have many fine witnesses who honor it, and justly so.
A good bit of the Scholarios letter to Cheilas comments on letters from him, overwritten and somewhat hysterical as was his style in distress (τοῖς γράμμασιν ἦν μετ´ὑπερβολῆς), but it also dryly indicates that their situations under Constantine had changed from what they previously had been under John:
You are abandoning us who have no wish to show contempt, and who respect the eagerness of a friend . . . Let this suffice us then. We share your happiness in the good will of our best leaders as we ourselves often enjoyed it in splendor, but now let us abandon and be free of it, thinking that we and you together with us are fortunate. We are enjoying this opinion equitably, and taking pleasure in a reputation for virtue in place of our former splendor. For we, along with them, shall celebrate the brother for his praiseworthy clemency -- don't you think? -- for through that all the best will come from both God and men.
You are prevented from writing frequently by the crowd of problems that surround you . . . Write, then, whenever you find it easier for you. . . . Write something short: that will be dearer and more precious than the longer effusions of others, and show by this your longing and purest feeling toward us as from the beginning.
Cheilas eventually returned to Mistra where he then became mesazon for Demetrios. In a letter to the Gemistos brothers, when their father died, Bessarion concluded:
Be well, and speak to Nikephoros Prinkeps Cheilas for me, telling him to know that he is loved by me for his goodness more than ever before.
There is much evidence for the emotionality of Cheilas' personality, and when hostile gossip produced hurt feelings , Eugenikos had written:
I learned from one of your countrymen here, a warm supporter of yours, and the good son of one of my associates, that certain ill-wishers here have corrupted the good and wise information that you receive, announcing complete untruths and have claimed that I have condemned you frequently and to many people when, by the grace of God, what I do is just the opposite, fervently and continuously. You are, with the aid of God one of those we praise, and we are not given to slandering.
John Eugenikos left his estate in Cheilas' care during his trip to Trebizond in 1454-55. Then he had a letter from his son George (the deaths of his younger brothers were discussed in the previous entry). Eugenikos wrote Cheilas with such graciousness that it becomes difficult to discover that Cheilas had been negligent. The wolves are a puzzlement: they are generally taken as raiding neighbors, but a mountain village on the slopes of the Taygetos range is likely to be a sheep-herding village and I suspect these are real wolves.
Not but that if you stood aside for a while from our common understanding and firm resolve for the better, something that happens to people who are distracted by many important things, as nature has it though it may be against their will, nonetheless keeping in mind the letter of warm mutual affection, and those bright hopes of ours for those around you, and what we set up for my son when I left, and you promised, what I begged from you in earlier letters for yourself and those under your care, a grant to us concerning everything where you are and whatever or ours there is. My son George needs help frequently, and the village along with him, which will provide for his and my survival when I, God willing, shall return. The village is frequently besieged, and excavations are dug under the fences by the wolves nearby, and who could be a better manager and a greater assistance for us than you, when you are led by God.
Again, thanks to Pierre MacKay for his translations.