The occasion of Filelfo's removal to Siena was this:—When his position at Florence had become untenable, he received an invitation from Antonio Petrucci to lecture for two years, with a stipend of 350 florins. Filelfo replied that he preferred small pay and quiet to a larger income among the swords and poisons of his envious rivals. Accordingly he took up his abode at Siena for four years in the Piccolomini Palace. Like many greater and more admirable men, he had a restless disposition, always pleased with what is new, yet always grumbling when the taste of bitter mounted to his lips. The most honourable invitations now began to shower upon him. The Council of Basle, the Venetian Senate, the Emperor of the East, Eugenius IV., the Universities of Perugia and Bologna, and the Duke of Milan applied for his services. It was not, however, until the year 1439 that his love of change, combined with the allurements of higher pay, induced him to close with the offers of the Senate of Bologna. Once more, then, he crossed the Apennines, and once more, after a brief sojourn of a few months, he again quitted Bologna, and transferred himself to Milan. His reception by Filippo Maria Visconti was most flattering. Placing a diamond ring upon his finger, the Duke welcomed him among the nobles of his Court on New Year's Day in 1440. Thus began Filelfo's connection with the Lombard capital, which, though often interrupted, was never wholly broken till his death.

The munificence of the Visconti exceeded that of any of Filelfo's patrons,[267] while the mode of life at Milan exactly suited his vainglorious temperament. He loved to throw his money about among lords, to appear at high Court festivals, and to take the lead on ceremonial occasions in his rank of orator. There was, moreover, no rival strong enough to threaten the blasting of his popularity.[268] We find him, during his residence at Milan, continually engaged in the exercise of rhetoric. Public and private incidents of the most various character employed his skill, nor is there any doubt that his large professorial income was considerably increased by presents received from patrons and employers.[269] In addition to the labours of his chair, he engaged in various literary works. His Satires and Odes were gradually growing into ponderous volumes.[270] Other fugitive pieces in prose he put together under the title of 'Convivia Mediolanensia.' Meanwhile he carried on an active correspondence, both familiar and hortatory, with the scholars and the princes of his day.[271] There was no branch of letters with which, sustained by sublime self-approval, he was not willing and eager to meddle. As he had professed Dante at Florence, so here at Milan, by ducal command, he undertook to comment upon Petrarch, and actually composed a poem on S. John the Baptist in terza rima. There is something ludicrous in the thought of this Visconti, would-be Herod as in truth he was, commissioning Filelfo, the outrageous Pagan, to versify the life of Christ's forerunner. If Filelfo despised anything more than sacred history, it was the Italian language; and if there was a task for which he was unfitted, it was the composition of poetry.

During the second year of his Milanese residence Filelfo lost his wife Theodora. He speedily married again, choosing for his bride a beautiful young lady of good family in Milan. Her name was Orsina Osnaga. Since I have touched upon this matter of Filelfo's private life, it may be well to add that when he lost his second wife, he took in wedlock for the third time Laura Magiolini. By each of his marriages he acquired no inconsiderable property, and all his brides belonged to highly distinguished families. The best thing that can be said about Filelfo as a man is, that he was undoubtedly attached to his wives and to the numerous children they bore him.[272] This feeling did not, however, protect him from numerous infidelities, or save his fortune from the burden of illegitimate children.[273] It is even doubtful whether credence should not be accorded to suggestions of worse debauchery, repeated with every appearance of belief by his enemies, and on his side but imperfectly refuted. Filelfo was, in truth, a man of great physical vigour, whose energies the mere labour of the student was insufficient to exhaust. Loves and hatreds, domestic sympathies and turbulent passions, absorbed a portion of his superfluous force; nor was he at any time restrained by scruples of religion or morality. What was good for Greeks and Romans was good for him. It is also to be noted that the innate sense of delicacy which sometimes forms the safeguard of excessive temperaments was altogether alien to his nature.

During the disasters that befell the State of Milan on the death of Filippo Maria, Filelfo at first espoused the cause of the burghers. A letter to the Florentines is extant, in which he exhorts them to aid their sister commonwealth at the extreme hour of her peril. It was not natural, however, that a humanist, who had no zeal for freedom, and whose personal interests led him to desire a settled government at any price, should continue staunch to a republic so unnerved as that of Milan. When Carlo Gonzaga played the Milanese false by admitting the troops of Francesco Sforza, Filelfo was the first to welcome the new monarch with a set oration. He professed great admiration for the general who, by careful management and double-dealing, had placed himself at the head of the third state in the peninsula. Yet his correspondence at this period proves that his mind was uneasy, and that he desired a change. In an impudent letter addressed to Nicholas V., he solicited ecclesiastical preferment, suggesting that the promise of a bishop's mitre would secure his splendid talents for the service of the Papacy.[274] However desirous the Pope might be to engage Filelfo for his translation factory at Rome, the price demanded was too great. He could not recognise a vocation so clearly inspired by mercenary motives; and to receive into the high places of the Church, at his own request, a man accused of many vices, who had twice been married, would have established a dangerous precedent. Filelfo, receiving neither substantial encouragement nor a flat refusal, turned his thoughts to matrimony for the third time, and addressed a prayer on this occasion to Dame Venus, in which he besought the mother of Priapus to befriend her votary. The intelligent student of the Renaissance will not fail to notice the state of mind implied by the juxtaposition of this letter to the Holy Father and this ode to Venus.

Filelfo was now fain to content himself with the patronage of Francesco Sforza, a prince who had no natural turn for literature, but who was wise enough to know that a parvenu could least of all afford to neglect the ruling fashions of his age. The letters he wrote at this period abound in impudent demands for money, querulous outcries over the poverty to which the first scholar of the century was condemned, and violent menaces of retaliation if his salary remained in arrears.[275] Not only Francesco Sforza, but all the patrons upon whom Filelfo thought he had a claim, were assailed with reptile lamentations and more reptile menaces. Alessandro Sforza, Lodovico Gonzaga, and three Popes in succession may be mentioned among the more distinguished princes who suffered from this literary brigandage.[276] Not without strict justice did a contemporary describe him in the following severe terms:—'He is calumnious, envious, vain, and so greedy of gold that he metes out praise or blame according to the gifts he gets, both despicable as proceeding from a tainted source.'[277] Filelfo's rapacity is truly disgusting when we remember that he received far more than any equally distinguished student of his age. Not the illiberality of patrons, but his own luxurious habits, reduced him to beggary. All the while that he was screaming in bad Latin verse, he lived expensively, indulging ostentatious tastes, and finding money for unclean indulgences. In order to confirm his claim on the Duke of Milan's generosity, he began a gigantic Latin epic upon the life of Sforza. Without plan, a mere versified chronicle, encumbered with foolish mythological machinery, and loaded with fulsome flatteries, this leaden Sforziad crawled on until 12,800 lines had been written. Only the first eight books of it were published in MS., nor were these ever printed.[278]

By fair means and by foul, Filelfo had managed to secure a splendid reputation throughout Italy. His journey to Naples in 1453 resembled a triumphal progress. Nicholas V. entertained him with distinction, read his infamous satires, presented him with a purse of 500 ducats, and offered him a yearly stipend of 600 if he would dedicate his talents to translation. Alfonso dubbed him knight, and placed the poet's laurel on his brow with his own royal hands. As he passed through their capitals, the princes received him like an equal. At Ferrara he enjoyed the hospitalities of Duke Borso, at Mantua the friendship of the Marchese Lodovico Gonzaga; the terrible Gismondo Pandolfo Malatesta welcomed him in Rimini, and the General Jacopo Piccinino in his camp at Fossombrone. Nor was this fame confined to Italy. On the fall of Constantinople he addressed a letter to the Sultan, beseeching him to release his mother-in-law and her two daughters from captivity; the humanist's eloquence obtained this favour from the Turkish conqueror, who refused to accept a ransom for the relatives of so illustrious an orator.[279]

Until the death of Francesco Sforza Milan continued to be the city of Filelfo's choice. After that event he turned his thoughts to Rome. Pius II., Paul II., and Sixtus IV., in succession, had testified their regard for him, either by moderate presents, sufficient to excite his cupidity and check his slanderous temper, or by negotiations which came to nothing. At last, in 1474, he received from Rome the offer of a professorial chair, with a stipend of 600 florins, and the promise of the first vacant post in the Apostolic Chancery.

The old man of seventy-seven years once more journeyed across the plains of Lombardy, ascended the Apennines, passed through Florence,[280] and began his lectures with the 'Tusculans' of Cicero, on the twelfth day of January, 1475, in Rome. The marks of favour with which Sixtus had received him were highly honourable. Filelfo was permitted to sit in the Pope's presence, and on Christmas Day he stood among the ambassadors while Sixtus celebrated mass. The vigorous old scholar at first felt that all his previous life had been a tedious prologue to this blissful play. Soon, however, a cloud arose on the horizon. The Pope's treasurer, Milliardo Cicala, was remiss in payments. Filelfo retaliated by describing Cicala's vices in the most lurid colours to Sixtus.[281] Though his style and eloquence were always vulgar, the concentrated fury and impassioned hatred of these invectives cannot fail to impress the imagination. Such a picture of the dissolute and grasping treasurer, painted by Filelfo and sent to Sixtus, has a sinister humour which might recommend itself to the audience of an infernal comedy. It is only necessary to have some knowledge of the three men in order to perceive its force. Nor did Sixtus himself long continue in Filelfo's graces. Frequent journeys prove how unsettled he became; at last he left Rome in 1476, never to return. When the Pazzi Conjuration failed at Florence, Filelfo wrote to congratulate Lorenzo de' Medici on his escape, and undertook the task of composing a history of the whole intrigue. Two long and violent letters addressed to Sixtus, accusing him of participation in the conspiracy, and heaping on him charges of vice, were the result of this determination.[282] These epistles were dated from Milan, whither Filelfo had retired in 1476, to find his third wife dead of the plague, and buried on the eve of his arrival. His sorrow on this occasion was genuine; nor is it likely that he derived much comfort from a curious epistle addressed to him by Paolo Morosini, who, himself a husband and father, attempted to console the septuagenarian professor by elaborate abuse of matrimony.[283] To such ridiculous vagaries did the rhetorical spirit of humanism lead its votaries.

Filelfo's last journey was undertaken in 1481. Ill at ease, and sore of heart, the veteran of scholarship still longed for further triumphs. All his wishes for some time past had been set on ending his days at Florence, near the person of Lorenzo de' Medici; and when an invitation to the Chair of Greek Literature arrived, it found him eager to set forth. He was so poor, however, that the Duke's secretary, Jacopo Antiquari, had to lend him money for the journey.[284] He just managed to reach Florence, where he died of dysentery a fortnight after his arrival, at the age of eighty-three. The Florentines buried him in the Church of the Annunziata.