Raymond McGuire, African-American Investment Banker (2006)

Max Can't Help It!
8 min readMar 23, 2021

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NOTE: I wrote this article in May of 2005. A couple of young men, my guess both someone Mr. McGuire was mentoring at the time, wrote me angry emails so I pulled the story (I hoped they’d feel heard). However, I’ve never forgotten it because I felt this story explained why someone like Barack Obama would win the Presidency. Because of that prediction and Mr. McGuire’s seeking to become Mayor of NYC I’m going to give this piece another try.

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Raymond McGuire (from mid 2000s)

The New Invisible Man

PLEASE NOTE: This piece is pure philosophical fantasy. I have never met Mr. McGuire or talked to people who know him. In the past week, some readers who say they know Mr. McGuire have commented that my portrayal is 90% inaccurate. I’m sure they’re right, though I hope you find some of the ideas interesting nonetheless.

Raymond McGuire, a top mergers and acquisitions banker, who is also an African American, made the headlines this week after his departure from the embattled Morgan Stanley for Citigroup. Most likely he just wanted to join his long-time associate, Joseph Perella. Curious, I searched for more information about Mr. McGuire, using Lexis, Factiva, ABI/Inform and all the major online repositories of business text. Nowhere could I find mention of Raymond McGuire’s parents or how he ended up at Hotchkiss, an exclusive prep school in Connecticut. The more I stripped away the facts the more I was left with an invisible man.

An invisible man Ralph Ellison wrote about, in his novel, published in 1952, about five years before Raymond McGuire was born.

In the 1981 introduction to The Invisible Man Ralph Ellison wrote that he originally planned to write the book about a black military officer during World War II. He wrote, it would “focus upon the experiences of a captured American pilot who found himself in a Nazi prisoner-of-war camp in which he was the officer of highest rank and thus by a convention of war the designated spokesman for his fellow prisoners. Predictably the dramatic conflict arose from the fact that he was the only Negro among the Americans, and the resulting racial tension was exploited by the German camp commander for his own amusement. Having to choose between his passionate rejection of both native and foreign racisms while upholding those democratic values which he held in common with his white countrymen, my pilot was forced to find support for his morale in his sense of individual dignity and in his newly awakened awareness of human loneliness.”

Is Raymond Mcguire, wealthy and powerful as he is, lonely? I believe yes. It is the same loneliness that afflicts very successful people of any race. But African-Americans like Mr. McGuire face additional pressures. Ellison wrote about his 1940s character,

“he had to either to affirm the transcendent ideals of democracy and his own dignity by aiding those who despised him, or accept his situation as hopelessly devoid of meaning; a choice tantamount to rejecting his own humanity. The crowning irony of all this lay in the fact that neither of his adversaries was aware of his inner struggle.”

This is exactly what struck me when I read about Raymond McGuire in the media this week. How could he affirm the ideals of capitalism when most people probably look at him as an affirmative-action exception? His resume is too perfect, too Harvard. A few years ago, when asked how to succeed on Wall Street, Mr. McGuire told a reporter, “I would say that what it takes to succeed here, if I could capture it in a few words, would be unequivocal commitment to excellence and distinction.” That’s what everyone (especially whites) says on Wall Street. But that everyone on Wall Street didn’t grow up in the racially difficult 60s and 70s.

For starters, while some people, both black and white, were fighting for social equality during Raymond McGuire’s youth, the intelligent blacks were suffering more than ever.

I saw this first hand. I’m four years younger than Mr. McGuire and I worked as a messenger, part time, on Wall Street during high school in the 1970s. Although my school was half black there were no black messengers. There were few jobs low enough on Wall Street that a black person could get them. At Hotchkiss, Raymond McGuire could distance himself from the race question, but not much. In the Westchester neighborhood where most successful investment bankers lived, Scarsdale, I had a girlfriend, who at the time told me about her friend who saw a black person riding on a bike outside the window and innocently asked her mother how that person “turned” black? True or not, the story captures the simple fact that most suburban whites did not live near, nor interact with, blacks in the 1970s.

Times may have changed for the current generation, but not Mr. McGuire’s or mine. At my 25th High School reunion only one black person attended though, as I said, half the school was African American.

What’s interesting to me, however, is not the passive question of Mr. McGuire’s loneliness, but the complex question of, if lonely in this specific black way, did it make Mr. McGuire more effective? I think it did. And I believe if you follow this chain of reasoning you will conclude that a black President is not only possible, but probable. We’ll have a black President because only a black President will have the mental toughness necessary to lead a country so at turns arrogant and self-pitying. But that’s another story.

Wall Street, it turns out, is a perfect arena for the mental strength of people like Raymond McGuire, and by that I mean black, Hispanic, Asian, et cetera, because, as Ellison wrote on page 1 of his book, “I am invisible, understand, simply because people refuse to see me. Like the bodiless heads you see sometimes in circus sideshows, it is as though I have been surrounded by mirrors of hard, distorting glass. When they approach me they see only my surroundings, themselves, or figments of their imagination — indeed, everything and anything except me.”

Smart people like Raymond McGuire, who recognize this, have exploited this handicap to their benefit. Whereas a white investment banker starts with the foundation of historical destiny, it also weakens them. A black banker is always struggling against perception, good or bad.

An investment banker, like Raymond McGuire, gets involved with two companies who want to merge, though it may start out as only one company wanting to acquire the other. At least, this is what you’ll read in the paper. It sounds very rational; it’s anything but.

In reality, there will be one person, say the CEO, who wants to initiate a deal, for reasons that are seldom spoken. He will have at least two right-hand men. There will be a couple of lawyers and a couple of lead directors on the board. In all, there will be at least seven people, probably more, who will all have slightly different agendas, personalities, hidden angers and desires.

There will be another seven people or more at the other company. So at minimum, Raymond McGuire will have to get at least 14 people to agree to a deal. To understand the enormity of that challenge think how hard it is to get 14 of your friends to agree on which restaurant to go to — 90 to 365 days in a row!

All Raymond McGuire has to do, like any other investment banker, is get them to the contract signing. This will require crafting a complex financial contract between the parties. During this journey they step outside and they aren’t two feet out the door when they come upon a puddle, blocking their way.

The investment banker says ‘no problem, I can fix this’ and lays face-down on the problem. This is what all investment bankers do, no matter what their color. If you had to compare investment banking to any martial art it would be Judo. The investment banker exploits weakness, the fact that the clients only see their needs and fears. The investment banker is just an, excuse the term, whore in their eyes. They don’t think he is smarter than they, just more connected.

Anyway, as the investment banker lies face down in our proverbial puddle, the fourteen principles then walk over the banker to the other side. The banker gets up from the slime and there is soot and soil all over his suit. He doesn’t act, in any way, that there is any crud on his person. His voice doesn’t quaver nor eyes twitch. They keep walking and the banker talks as confidently as ever.

Till another dirty puddle blocks their path and again the investment banker lays down in the dirt and grime. While the principles are walking over the banker, one brings up an arcane problem with an accounting issue with an offshore subsidiary in a supplemental set of books. After the banker gets up he offers a potential solution to the problem, not forgetting to give credit to one of the people who just stepped on his back, whether they thought it up or not.

The group is amazed that the banker was able to think through the pain and grasp the situation perfectly and know the exact solution to the problem.

After many episodes where the banker gets down in puddle after puddle the group stands in awe at the strength and personal integrity of the banker, his ability to maintain his wits and his poise. They start to give him some credit.

This gives them confidence. Because, for all their wealth and perceived power these are weaker men. Much weaker than the investment banker. They don’t know, they don’t really know, how to get down in that puddle to get ahead.

Long before Raymond Mcguire ever laid down on a puddle as an investment banker, he had to bear a million little humiliations to put his intelligence in play.

The black community is not a home to exceptionally smart people like Raymond McGuire. The smart black executive probably doesn’t know who to avoid first, the white people who believe in a, quote, black community, or the shrewd African Americans who make a very profitable living selling the black-community-con to the white community; Jesse Jackson’s Rainbow Push, for example.

The meaning of life is best found when no meaning was placed in the box before you opened it. Raymond McGuire has, and had, no such luxury. I doubt I would have written this piece about a white investment banker. Just another reminder of how much (I’m sure he would think idiotic) scrutiny smart black people must withstand. A final proof Mr. Raymond McGuire is an extraordinary person for reasons well beyond the depth of most business media.

— Max Rottersman

NOTE: I have never met Raymond McGuire and I expect he will not approve of this piece. What investment banker would? So keep in a mind, it is a fantasy using Mr. McGuire only as the theoretical starting point.

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Max Can't Help It!
Max Can't Help It!

Written by Max Can't Help It!

Trying to connect what hasn't been connected.

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