The "Chicago Way" to Trust

Having been born in the 70s, I am the age for Timothy Dalton to have been my James Bond, but very few people would describe him as the James Bond.  More often than not, that title goes to the late Sean Connery.  I would have never known either, had my parents not encouraged me to go see something on a different screen when they wanted to catch a movie on date night.   In the summer of 1987, while I was watching Dalton play 007 in The Living Daylights, Connery was playing Chicago Police Officer Jim Malone on a different screen in The Untouchables.  Despite having defined the character of James Bond for generations of moviegoers,  the role I always associate with Sean Connery is that veteran Chicago beat cop, working alongside Elliot Ness (Kevin Costner) to take down Al Capone (Robert Deniro).

In “3  Ways to Spot an Imposter” I described some red flags to warn you that the person you’re dealing with might not be who or what they are pretending to be.  In an early scene in The Untouchables, Jim Malone teaches a brief lesson on how to know if someone who is precisely whom they claim to be.   The scene takes place on a bridge, at night, where Malone and Ness meet for the first time...

Malone: Why are you packin' the gun?

Ness: I'm a Treasury Officer.

Malone: All right. Just remember what we talked about now.

Ness: Hey... Wait a minute!  What the hell kind of police do you have in this ******* city? You just turned your back on an armed man.

Malone: You're a Treasury officer.

Ness: I just told you I was.

Malone: Who would claim to be that, who was not?

Who indeed?!  If a person was going to excuse the presence of a pistol, I am certain there are half a dozen easier explanations (FBI, CIA, Secret Service, Private Security, “I have a permit”…).  Malone understood that NOBODY’s knee-jerk cover story would be “I’m a Treasury Officer.”

One way to turn this concept into practical advice is this: In deciding who to trust, keep an eye out for those whose claims do not fit perfectly what they think you want to hear.  In the world of financial advice, someone may mention a financial mistake that they had made in their past.  Such vulnerability is seldom dishonest since it is not at all self-serving.  In my own first meetings with potential clients, I volunteer some reasons that others may have found me to be a less-than-ideal fit for them.  This might have to do with how I build ultra-diversified portfolios (boring), how I disclose their fee calculation on every statement (some people would rather not look), or simply how I almost never wear suits to work.  My thinking is that everyone is better off knowing about any potential incompatibility sooner, rather than later.  Someone who is in it for the quick buck doesn’t think about “later”, much less about what is good for anyone but themselves.  An imposter will just tell you what you want to hear.

”Here endeth the lesson.” - Jim Malone (as played by Sir Sean Connery [August 25, 1930-October 31, 2020])

Related: The Two Keys to Survival