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Bill Simmons: From Mailbag to Made Big

Nothing is original. The knowledge we have and the personas we take on are nothing but facsimiles of personalities from the past. This is definitely the case when it comes to my writing and the way I conduct my podcasts. Without knowing it, the copious books I read in the past and the endless times I spent watching my favorite broadcasters were in actually training sessions where I was learning from the best. I was like a mix between two of the main characters from my once favorite show Wonder Years, either I was entranced by the television like Kevin or I was acting every part the nerd reading copious books like Paul.

It was these two traits, watching TV like Kevin in ways that I could discern the minutia of every shot and concurrently reading and consuming books vociferously like a famished lion, that led to me seeking journalism as a major in college. But when I realized that journalism was subjective analysis covered in the guise of objectivity, I quickly decided to exit that path and chose mass communication instead. Meaning I chose not to commit and instead just committed to passionately pursuing the art of communication and vigorously pursued knowledge. In all honest, I guess you can say my first love was information—I could not get enough data and discovering new “facts”.

I am just like all writers who came before me, I am standing on the shoulders of big people which is why I am able to stand tall enough to observe and note the world about us. The giants who influenced me were many, writers like Ernest Hemingway, Alex Haley, Ralph Ellison,  William Faulkner, Angela Davis and William Faulkner, to be honest limiting the list of my favorite authors to just a few gives me anxiety thinking about whom to omit from my list. Even more than painters and musicians, writers hold a place in my heart that is reserved only for those who are able to transform words into an art. As far as I am concerned, when the greatest of writers start click-clacking away on their typewriters or start jotting on their notepads, it is one word that is worth a thousand pictures.

Let me add an unlikely name to the list of writing big people. Ladies and gentlemen, I introduce you to Bill Simmons. Yes, the same Bill Simmons who was once on ESPN by way of Grantland then on HBO and now can be found on his own media entity the Ringer. But to me, Bill will always be the Sports Guy, the once prolific writer who covered sports through the eyes of a fan. You see, that is what makes Bill special in my eyes. Bill was one of us, just a regular guy who had an extraordinary talent to put words together in a way that conveyed narratives. The narratives he wrote were brilliant because they were at once relatable yet so wonderfully original and unique.

At the core of Bill’s writing was a wit and a humor that he used to make the reader smile even when their particular team was ripping their hearts out. Bill grew up a sports fan in Brookline, he was every bit as Boston as clam chowder and Fenway park. This is what initially drew me to Bill’s writing, although I grew up in the Washington DC suburbs, for some odd reason most of my favorite teams outside of the DC football team were all Boston teams. I was a Celtics fan in the heydays of the Larry Bird and Magic Johnson rivalry. I was one of the few brown skinned guys to make no secret of the fact that my favorite basketball player was the redneck from French Lick. After the 1987 Red Sox debacle and the crushing defeat the Sox suffered at the hand of the Mets, I became an avowed Red Sox fan. Loyalty to a team only begins, by the way, when that team has torn open your chest cavity, yanked out your beating heart and crushed it like Scorpion on Mortal Kombat.

Bill and I thus traveled a parallel path. For close to two decades, I suffered as a Red Sox fan witnessing one collapse after another. It was after the implosion of the Sox and Grady Little’s still controversial decision to leave in Pedro Martinez that I discovered the styling of Bill Simmons. In search of some type of elixir to fix my bleeding heart after the Red Sox somehow gave away a game to the hated Yankees during the 2003 ALCS, I ran into the mailbag. Instantly I was hooked, Bill found a way to make me laugh through the melancholy that the Red Sox had inflicted on my soul.

Only those who have experienced the writing of Bill Simmons would understand just how addictive his missives are. It was not so much written words as much as the feeling that Bill was able to convey that he was actually talking directly to us. To this day, I chuckle when I think back to the ways his avid readers would curse him in the quotes he used in his mailbag articles because he did not write an article in a timely manner. The mailbag was an interactive blog that Bill Simmons used to take questions from his audience—questions about sports, life, love, politics, anything and everything was permissible to ask the Sports Guy. His responses used a mix of humor and insightful observations to induce both a levity and enlightenment to his readers.

I would soon find out that Bill’s talent went beyond just the mailbag. Simmons was communications in ways that defied logic. His ability to fill up articles on demand, to write topical articles almost the minute a particular game or an event took place, was awe inspiring. Remember how I said I am but a man standing on the back of big people? Well this is why I included Bill in my list of all time greats because he was the one who inspired me to write conversationally and to write on a whim. Bill wrote about anything and everything sports and beyond;though sports was his number one love, he also wrote just as profoundly about movies, songs, and current events. This is why Bill had a massive following, he offered original thought instead of vacuous banter—nothing about Bill was scripted.

So a common man with an uncommon gift writing in his living room about sports soon enough found a niche then grew that niche into a mini-empire. Soon enough, the gargantuan came knocking as ESPN made an offer he could not refuse. Bill would end up moving to Los Angeles, a topic of much jeer to his Boston fans, and then started Grantland under the ESPN umbrella. Grantland was an homage to Bill’s sport journalist hero Grantland Rice. All the sudden, Bill went from local to corporate and that is where the journey took a twist. Fame has a cost, the same thing that made Bill a hero to his fan base, his freestyle non-scripted ways, would soon enough land him in hot water in the corporate halls of Bristol. When Bill made one too many unscripted—yet true—remarks about the NFL, ESPN decided to cut ties with Simmons. ESPN chose to remain in the good graces of the NFL conglomerate instead of standing by their employees. Who has time for free speech and truth telling when there is an NFL contract to be one and commercials to be sold!

Bill, to his credit refused to be muffled. He chose the honorable path out instead of taking a shellacking like a lot of color commentators and analysts take from the corporate whip in order to retain their proximity to Sports Inc. Bill learned a valuable lesson that all of us should note. Instead of submitting to the beast that is corporate America, he chose to be a free agent and an entrepreneur. Although he tried his hand once again at HBO, in the end he realized that the only way he could retain his authenticity and remain true to his roots was to start his own media company. And that is exactly what Bill has done; he invested his time, talent and resources to starting the Ringer.

Bill built up a massive following over the past 20 years, what started with email exchanges between his readers has now grown into a massive footprint where Simmons has over five million followers on Twitter alone! As I noted before, Bill has redefined communications as far as I am concerned. He is still able to write on demand on topics ranging from sports to movies and pop culture, he then jumps on a podcast to interview guests or pontificate on his own, or he appears as a guest on some TV show. One can become a global icon if he/she is determined in the face of rejection and has a gift to gab and write.

Thank you Bill Simmons for being an amazing writer and a terrific humorist. I’ve been meaning to write this for a while to thank you for the times you made me laugh through my moment of loss. No I’m not referring to sports, the time that I was the most dependent on your mailbag articles and your take on sport was when I had broken up with my ex-fiancee. This is the beauty of sport isn’t it, it lets us escape the nagging reality of life and instead lets us live in two hour increments of excitement. By the way Bill, you and fellow Bostonians should thank me personally for the Red Sox for “the Curse” was finally broken on October 27th 2004 which happened to fall on my 30th birthday. And I was right on Yawkey Ave partying it up with the rest of Boston Nation!

I don’t ask for too much from Boston for being the reason why the Red Sox won the world series other than a statue next to Ted Williams in front of Fenway Park. Something tells me that the Yankees have a better shot at getting a ticker tape parade through the Canyon of Heroes before I get a ticket to a Red Sox game let alone a statue next to “the Splendid Splinter”. I’ll just be happy with the memories of 2004 and the magical season and I’ll have the sweet satisfaction of forever holding the trump card of “remember 2004” when a Yankee fan tries to gloat about their bought and purchased rings!

Here is to the sports guy in all of us and a special thank you to Bill Simmons who translated his passion for sports into a gift that gives to him as well as gives back to others. If you have not gotten a chance to find out about Bill yet, he is a must follow on twitter (link), definitely check him out at the Ringer (link) and for old times sake, check out one of his hilarious mailbag articles (link). While you are at it, if you have a talent to write or the gift to reach people, be like Bill and take your talent to your own platform. Instead of throwing your pearls away for free on Facebook, start a website and see if your insights and perspectives can garner an audience. Bill was able to translate his talent into a small empire where his words are read and listened to by millions.

The mass media is dying because they are too scripted and too far gone into the profit chasing hole to dare to be authentic. Bill dared to be different, which is why ESPN could not stomach anyone who could actually articulate something original. Be just as audacious and try the same, who knows you just might be the next sports guy. In an age where originality is lacking, people are always on the lookout for anything that can make them either think or smile. Be like Simmons and see if humble beginnings can lead to a profession based on passion instead of work. It worked out pretty well for Bill and it’s going pretty well for me as well. But then again, I just followed in the steps of Red Sox…what did you think I was going to say the G word at the end after avoiding the New York football team’s name throughout this article? #BillMadeBig

Dedicated to Red Sox nation and New England sports fans world-wide #BostonStrong

Dedicated to Yankees and Giants fans world wide


Come on New York, don’t take it personal, we are allowed to joke about sports, besides NYC has the Knicks….ooops…let me stop before I lose the entire New York market for Ghion. 😉
Teodrose Fikremariam
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Teodrose Fikremariam

Writer at Ghion Journal
Teodrose Fikremariam is the co-founder and former editor of the Ghion Journal.
Teodrose Fikremariam
Follow Me

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