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 degree in canon and civil law (, i. 183; ). His choice of university must have been decided for him by his maternal uncle, Simon Islip (afterwards archbishop of Canterbury) [q. v.], to whom Whittlesey owed his education and much ecclesiastical promotion. He was collated archdeacon of Huntingdon in June 1337, according to a record quoted by White Kennett; but if this be correct, he was reappointed by letters patent on 20 June 1343 (, ii. 50). In the plague year (1349), when his uncle became archbishop, Whittlesey was made (10 Sept.) ‘custos’ of Peterhouse at Cambridge, but held this position only until 1351. He was a prebendary of Lichfield from 1350, and of Chichester and Lincoln from 1356, retaining the last down to his appointment as primate (ib. i. 626, ii. 106). He had also a prebend at Hastings (, p. 784). Along with his archdeaconry and prebends Whittlesey held the benefices of Ivychurch, near Romney (1352), Croydon (1353), and Cliffe, near Rochester (ib.; Anglia Sacra, i. 535). He is said to have acted for a time as his uncle's proctor at the papal court, and was certainly sent on a mission there by the king in 1353 (ib.; Rot. Parl. ii. 252; Fœdera, v. 747). Islip made him first his vicar-general, then dean of the court of arches, and finally secured his election (23 Oct. 1360) to the dependent see of Rochester, not, it would seem, without a bargain with the monks (, ii. 564; Registrum Roffense, p. 181;, iv. 224). The pope gave his consent by way of provision on 31 July following, and, owing to Islip's infirmities, Whittlesey's consecration was quietly performed in the chapel of the archbishop's manor-house at Otford, not a single diocesan bishop being present (ib. iv. 225;, u.s.). Two years later (6 March 1364) he was translated by Islip's influence to the richer see of Worcester, but does not seem to have resided (ib. iii. 58; cf., iv. 226).

After his uncle's death in 1366 Whittlesey can hardly have looked for further promotion, but fortune still stood his friend. Langham, Islip's masterful successor, accepted a cardinal's hat without the royal permission, and had to resign. A more colourless and pliant primate being desiderated, the choice fell upon Whittlesey, who was accordingly translated to Canterbury by a papal bull, dated 11 Oct. 1368 (, i. 19). He received the temporalities on 15 Jan. 1369, the pallium on 19 April, and was enthroned on 17 June, the usual feast being dispensed with on account of the plague. Whittlesey would hardly have made his mark in the primacy, even if he had not very soon become a confirmed invalid. He was unable in consequence to take part in the defence of the church in the memorable parliament of 1371, and rarely left his quiet refuge at Otford (, iii. 89;, iv. 228). But the pressure of taxation upon the clergy became so heavy that he dragged himself up to London for the meeting of convocation in December 1373, and ascended the pulpit of St. Paul's to make his protest; but he had not proceeded far when he swooned in the arms of his chaplain, and was carried out and rowed to Lambeth (, p. 380;, iii. 97). He lingered until 5 June, when he made his will, bequeathing his books to Peterhouse, and the residue of his property to his poor relations. His register appears to give this as the day of his death (Anglia Sacra, i. 794;, i. 20). But the record of Canterbury obits places it on the 6th (Anglia Sacra, i. 61). The date in Walsingham (i. 317)—5 July—though the month is obviously wrong, rather confirms the former statement. Perhaps he died in the night between the two dates. His remains were taken to Canterbury and buried in the cathedral near the tomb of Islip, between two pillars on the south side of the nave (, Antiquities of Canterbury, pt. i. p. 134). His epitaph, inscribed on brass, remained legible about 1586, when it was read by Godwin; but only a fragment survived when it was seen by Weever, who published his ‘Funerall Monuments’ in 1631.

It was Whittlesey who obtained from Urban V a bull exempting the university of Oxford from the jurisdiction of the bishop of Lincoln. The story in the ‘Continuation of the Eulogium’ (iii. 337–8) of the great council of prelates and lords called after Pentecost (20 May 1374) to discuss a papal demand for a subsidy to be used against the Florentines, in which the Black Prince is represented as calling Whittlesey an ass, is disposed of, so far as the latter is concerned, by the fact that he was on his deathbed at Lambeth when the scene is supposed to have taken place at Westminster. Nor is this the only incredible feature of the incident as there related.

[Rot. Parl., Rymer's Fœdera, original edit., Walsingham's Historia Anglicana and the Eulogium Historiarum (in Rolls Ser.); Anglia Sacra, ed. Wharton; Godwin, De Præsulibus Angliæ, ed. 1743; Wilkins's Concilia Magnæ Britanniæ et Hiberniæ; Tanner's Bibliotheca Scriptorum