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Michael Douglas in 'Wall Street Money Never Sleeps'As a follow-up to my last blog post about the mentoring mistakes I’ve made, I thought I would write about the World’s Worst Mentors. Sadly, I have reverted to fictional characters in film roles to explain why they are such bad mentors, getting the “inside scoop” on real-life mentors was just too difficult. Still, the shared ideal between all my terrible mentors is their belief in themselves. They are not typical villains, but, anti-heroes who felt they were doing what was necessary to serve themselves; their families, their businesses, their friends and in one case, the empire. How wrong they were! So, my top five of the ‘World’s Worst Mentors’ are:

1.Gordon Gekko – Wall Street [1987] & Wall Street: Money Never Sleeps [2010]

Master of the memorable line “Greed is Good”, Gordon Gekko (Michael Douglas) has to take the No 1 spot in the list of the ‘World’s Worst Mentors’. In Wall Street he corrupts rookie trader Bud Fox (Charlie Sheen) into dealing in inside information; selling commercially confidential information about his father’s airline company, lying and cheating – all for the sake of making money for Gekko, the corporate raider! In Wall Street: Money Never Sleeps, Gekko has served his prison sentence and is released: he corrupts his daughter’s idealistic stock broker boyfriend Jake Moore (Shia LaBeouf) into sneakily signing over access to his daughter’ Swiss trust fund account so that Gekko can deal himself back into business. “It’s not about the money. It’s about the game between people” he says, before adding that “money is a bitch that never sleeps!”Gekko has to be the world’s worst mentor, not because of his manipulation of his two mentees (Bud Fox and Jake Moore), but, for the sheer influence he has on real life brokers and traders! Oliver Stone, the director of Wall Street and the sequel was appalled that so many of them looked to model themselves on the character of Gordon Gekko. Sadder still is that many of the characters in Wall Street are modeled on real life traders like Ivan Boesky and Michael Milken, involved in the insider trading scandals in the 1980’s. Truth certainly is stranger than fiction.

2. John Milton – The Devil’s Advocate [1997]

No 2 on the list is John Milton (Al Pacino) who corrupts young hotshot lawyer Kevin Lomax (Keanu Reeves). The film thematically raises the preposition that ‘is winning everything’ in culture dominated by making money. As Kevin is transplanted into the fast paced New York City and showered with gifts, he finds himself adrift from his own moral compass. It is only once his wife is committed to mental institution for seeing devilish apparitions that Kevin realises that his boss (Al Pacino) is Lucifer himself!

“Who, in their right mind Kevin, could possibly deny the twentieth century was entirely mine”, John tells his protégé “Underestimated from day one. You’d never think I was a master of the universe, now would ya?”! No, we certainly wouldn’t, but for sheer perseverance in pandering to the seven deadly sins, vanity is his favourite vice apparently, John Milton snags the No 2 spot on the ‘World’s Worst Mentors’ list

3. Vito Corleone– The Godfather (1972), The Godfather II (1974)

Don Vito Corleone (Marlon Brando) is the epitome of the world’s worst mentor and steals the number 3 slot on the ‘World’s Worst Mentors’ list. The star of Francis Ford Coppola’s first two Godfather films; Vito nurtures his younger son, Michael Corleone (Al Pacino) with advice like “I make him an offer he don’ refuse. Don’ worry” and “there are people in this world who go about demanding to be killed. You must have noticed them. They quarrel in gambling games. They jump out of their automobiles in a rage. They humiliate and bully people whose capabilities they do not know. These are people who wander through the world shouting, “kill me”. And there’s always someone ready to oblige to them!”

However, Don Corleone is included in this list not only for obliging people by killing them, but also for the decapitated head of a horse scene in The Godfather film. The “Capo di Tutti Capi” (“boss of all bosses”) indeed!

4. Supreme Chancellor Palpatine – Star Wars Episode II – VI

Supreme Chancellor Palpatine (Ian McDiarmid), also known by his Sith name Darth Sidious, is the central villain of the Star Wars saga. He is the one who connives to turn Anakin Skywalker (Hayden Christensen ) into his Sith apprentice by preying on his fears of loss. Palpatine convinces Anakin to kill Count Dooku. He spends the next several days grooming Anakin, convincing him that turning to the “Dark Side” will allow him to save his wife from death in childbirth, and that having a Sith Lord in charge of the galaxy will bring stability.

Anakin resists at first, but later relents, and ends up helping Palpatine kill Mace Windu. In the fight, Palpatine is permanently disfigured but accepts Anakin as his apprentice and renames him Darth Vader. He sends Vader to kill all the separatists, and at the next session of the Senate, declares himself Emperor. However, Vader is seriously injured in a duel with Obi-Wan Kenobi so Palpatine has him encased on a robotic body and suit!

In Star Wards Episode VI Return of the Jedi, Palpatine looks to turn Vader’s son Luke Skywalker to the “Dark Side” encouraging a light sabre dual between father and son with unexpected consequences.

For sheer villainy and looking to stretch his influence across two generations, Palpatine takes the No 4 slot in this list of the ‘World’s Worst Mentors’.

5. Katharine Parker – Working Girl [1988]

The only woman on the list of the ‘World’s Worst Mentors’, Katherine Parker (Sigourney Weaver) in the 1988 film ‘Working Girl’ is certainly the finest example of the species. Boss to the hapless Tess McGill (Melanie Griffiths), Katherine shows the subtlety of female mentors over male ones. She asks Tess to forward business ideas to her, deleting Tess’s name and re-branding them as her own before forwarding them to her boyfriend Jack Trainer (Harrison Ford). Injured in a skiing accident, Katherine asks Tess to run errands, pick up her dry cleaning, vacuum her apartment whilst also advising Tess “Never burn bridges. Today’s junior *prick*, tomorrow’s senior partner”.

Katherine contrives to get a marriage proposal from Jack Trainer with “We’re in the same city now, I’ve indicated that I’m receptive to an offer, I’ve cleared the month of June… and I am, after all, me.” Priceless!

Sadly, the film then disintegrates into a mushy romantic comedy with the witty Ms Parker booted out on her “bony ass”! Shame, as she really did get some of the best mad mentor lines.