Harcourt "Harry" Woolf is the DSU (Detective Superintendent) at Stopford House in 1974 and Gene Hunt's former mentor. He first appears in the second series premiere, discussing the 'mugging gone wrong' with DCI Hunt and DI Sam Tyler. He comes across as a good street cop navigating the shark-infested waters of his current, more political, post. From the pictures in his office, he seems to have been at least as rabid a Manchester City fan as Hunt.
Harry Woolf is fond of Gene Hunt, as his own former 'boy wonder', and draws comparisons with Sam which, slightly surprisingly, Hunt does not refute exactly, adding the rider 'minus the looks, of course'. Presumably in protection of his own career, Woolf is anxious that the Tony Crane case be handled by the book, and not offer opportunities for claims of police misconduct. He keeps an eye on proceedings throughout.
In the next installment, the team are introduced to, in Woolf's words, 'Arnold Malone. He'd be my nemesis, if he knew how to spell it.', a crime boss who, it seems, engineered the springing of Dickie Fingers from the custody of Sam, DS Carling and DC Skelton. As Woolf approaches the sunset of his career, Malone is his 'Moby Dick', the one that got away, and the team undertake to make every effort to put him away - legally, Sam hopes.
Malone, pulled in for questioning, taunts Woolf, and is nearly assaulted by him.The matter is further complicated when Sam discovers Woolf taking meds in the locker area, and is informed, in secrecy, that his superior has terminal cancer. Meanwhile, Gene's sources tell him he's looking for a new mastermind behind the recent robberies, a Mr. Harcourt.
Dickie Fingers, when 'reacquired', refuses to talk with Hunt in the room, and, when he leaves, proceeds to tell Sam that the 'new boss' is, in fact, Harry Woolf, the man who was behind the original production order that saw Dickie transferred from prison into police custody. Uncertain of what to do, Sam has an uncomfortable encounter with Woolf when the latter wants Dickie sent straight back to prison. Hunt's reaction to Sam's report is to take the handset of a telephone and bash Dickie's hands, claiming that he (Dickie) is just a mouthpiece for slander by Malone.
Sam insists that they 'do it properly' and inform Woolf of the accusations against him and investigate them. Woolf is pleased to see procedure observed, and the matter appears to be laid to rest. Sam, however, is not satisfied, and enlists Glen Fletcher's help to tail Woolf. The DSU quietly informs his old DI, and Hunt turns up and abducts Sam. When the testosterone clears, they find themselves looking at the corpse of Dickie, who has been executed by a professional hitman.
Another confrontation with Malone leads to Hunt changing his tune, and deciding 'we sort this out ourselves' as he and Sam track down Woolf. Using Fletcher as a decoy, the duo raid Woolf's office, finding, thanks to Hunt's knowledge of him, the Lancashire Building Society bank book and cash hidden behind various pictures. The deposit account is in the name of Mr. Harcourt Woolf, which infuriates Hunt, since it shows that 'the street' knew before he did that his superior was bent. They then hear over the radio that Fletcher has been 'made' by Woolf, and dumped out of his car. Woolf is on his way back.
When the DSU appears, he attempts to bluster his way through, asking Hunt to remember his contribution to the city and let him vanish with his money, then draws a gun. Hunt then points his gun at him, but Woolf gets in his head, causing him to doubt his own ability to arrest his father figure. Fletcher, however, has made it back to Stopford House, and also draws on Woolf, while Sam tries to defuse the situation. This Gordian Knot is cut by Hunt shooting Woolf in the leg, and Fletcher disarming him. Hunt's last words to Woolf are "I'll call you an ambulance. Guv.". When, later in the pub, Sam says, "He'll die penniless and alone, then.", Hunt's instant response is, "No, I won't let that happen.".
It seems hard to credit that Gene Hunt could work as his DI and be unaware of his legal name.