Denny Crane, played by William Shatner, in the legal drama Boston Legal is one of my all-time favorite characters. Josh Bell, TV Critic for Las Vegas Weekly, describes Denny as “egomaniacal, sexually ravenous, prone to malapropisms“. That’s an apt description. In the show, Denny is a “renowned attorney of some fifty years of practice, who claims to have won 6043 cases and will never lose one”. With such an impressive resume, he sure has some life and business lessons for all of us.
3 Business Lessons from Denny Crane

1st Business Lesson: “There is always a way out”
Here’s a quote from Denny early in Season 1 of the show: “The secret of both trial law and life – pull a rabbit out of your hat”.
In life, business and sports, we have all witnessed several last moment miracles. Miracles because all hopes of a favorable outcome was lost. Yet, time and again, the underdogs claim victory.
They as Denny says, pull a rabbit out of their hats. One last trick, one last swing. It starts with a belief. A belief that not all is lost. A miracle is just around the corner.
When a man, although fictional, who has won more than 6000 cases, tells you that the secret is to pull a rabbit out of your hat, you better believe him.
Never give up as there is always a way out.
2nd Business Lesson: “Failure is not the end of the road”
Another quote and another business lesson – “If all else fails and you think you’ve lost, pretend you’ve won. Works for the president”.
Success and failure have something in common. They both don’t last long. Failure like success is often temporary.
A boxer is as good as his last bout. Memories of innumerable wins get shrouded by a resounding defeat. Boxing at the highest level is a tough sport. It is never easy to bounce back from a defeat. There is a lot at stake – sponsorship, fandom, pride.

You have to pick up the pieces, stand up again.
Okay, easier said than done. That’s where this advice from Denny works – “Pretend you’ve won”.
Losing or winning in sport, trial law, life or business happens first within us. What happens in the ring is the show we put on for the rest of the world.
Recovery from failure is shaped up by our thoughts and beliefs. Pretend to be a winner when all else fails. Yes, it is a false assurance but assurance nevertheless.
“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end.” – Denis Waitley
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When the world mocks you and looks down upon you, you have to be your own north star. Let positive thoughts and a winning attitude guide you back on your path to glory.
3rd Business Lesson: “No one can take away your freedom to choose”
“No matter how hard your day, no matter how tough your choices, how complex our ethical decisions, you always get to choose what you have for lunch.” – Denny Crane
More than anything, its our choices that define our destiny.
Life always gives us more than one choice. Right or wrong, we make the choice.
When your back is against the wall and you are at the lowest point in your life, career or business, you still get to choose your next step. In Denny’s words “you get to choose what you have for lunch”.
Do you want to choose not to stand up again?
Or do you want to regroup and get ready for the next bout?
It’s amazing how doors open up when you start looking for them. The world in that sense is a fantasy land. Opportunities lie hidden in a maze of self-pity and self-doubt. Rise above them and the vision gets clear.
Denny Crane – The Life Coach
Fiction proves to be a mirror for real life. Life inspires fiction and fiction inspires life. Today, we get to choose one of the iconic fictional characters, Denny Crane, to show us the way.
He is witty and with his unique sense of humor is always ready for a clever quip. Let us summarize the 3 life and business lessons we can learn from Denny Crane.
- No matter how bad the situation, no one can take away your freedom to choose what’s next for you
- Failure is never the end of the road. Regroup, learn and use it as your stepping stone
- If you look for it, there is a rabbit in your hat. Pull it out for that miracle. There is always a way out
Thank you Denny.
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Recommended Reading – Leadership Lessons from Dan Brown’s Bestseller “Inferno”
When in a position of power and leadership, our views are obstructed by ego, pride and a false sense of security. It’s unwise to reject unpopular suggestions without due consideration.
I am a strong believer in the statement “fiction imitates life”. I have often derived the best of life, business, relationship and leadership lessons from fiction. Great authors are great gurus.
Here are two leadership lessons from Dan Brown’s bestseller Inferno.