Muggles' Guide to Harry Potter/Characters/Dexter Fortescue

Overview
Dexter Fortescue, only seen as a portrait in the Headmaster's office, is described as 'a corpulent, red nosed wizard'.

Order of the Phoenix
Although he is not named, we see Fortescue shortly after the attack on Arthur Weasley. Having collected all the Weasley children and Harry in his office, Professor Dumbledore attempts to wake up Phineas Nigellus Black's portrait, to confirm that Sirius Black is ready to receive a large number of visitors. Phineas expresses unwillingness to help, at which the other portraits in the office express indignation. Three are particularly vocal, those being the wizard later identified as Fortescue, Armando Dippet, and an unnamed witch with a particularly thick-looking wand, almost a cudgel, who offers to chastise Phineas.

Fortescue is first named when Dolores Umbridge is explaining to Cornelius Fudge how she learned about Dumbledore's Army first meeting in the Hog's Head. She explains that Willy Widdershins had been there and reported back. Professor McGonagall, also present, comments that she had wondered how Willy had gotten off so lightly after all those regurgitating toilets, and Fortescue erupts, saying that they did not cut deals with petty criminals in his day. Dumbledore responds, "that will do, Fortescue."

When Dumbledore sends Harry to his office after the battle in the Ministry, Fortescue is among the first portraits to awaken and notice that he is there. He asks if this means Dumbledore will be returning, and comments that it has been dull in his absence. He also remarks that Dumbledore holds Harry in high esteem.

Deathly Hallows
After the final victory at the Battle at Hogwarts, Harry returns to the Headmaster's office to speak with Dumbledore's portrait. As he enters, he is greeted with loud cheers and applause from all the portraits. Dexter Fortescue is mentioned by name, waving his ear trumpet.

Strengths
As he is a former Hogwarts Headmaster, Fortescue was presumably a very intelligent and magically proficient Wizard during his lifetime. He appears to have an assertive personality, freely speaking out with his opinions. He appears to have a good opinion of Harry, and apparently feels it is important to mention that Dumbledore thinks highly of him.

Weaknesses
Judging by the ear trumpet seen in his portrait, Fortescue must have had some hearing loss, probably due to advancing age.

Relationships with Other Characters
As they share a common surname, Dexter may be an ancestor of Florean Fortescue, owner of the ice cream parlour in Diagon Alley. Florean has a vast knowledge about medieval witch burnings and seems to have an aptitude for teaching, suggesting he could be related to the former Headmaster. Nothing in the books either supports or refutes this relationship.

Along with the other Headmaster portraits, Fortescue acts as advisor to Albus Dumbledore and assists him as needed. He also speaks his mind to the other Headmaster portraits, vocally chastising anyone who he believes is acting inappropriately.

Fortescue appears to like Harry and interacts with him more than the other portraits.

Analysis
Fortescue quite clearly has rigid ideas about propriety, and readily expresses them. He probably sees his role in the office panoply as being the guardian of The Correct Way, as clearly everything has deteriorated so badly since he was Headmaster.