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Writer's pictureTerry Pace

If I Were Free

Updated: Oct 11, 2020

By Jesse Winchester (RIP 1944 - 2014)


Jesse Winchester is one of my favorite singer-songwriters. I have typically listened to him at least once a week for the past 20 years. His songs are well crafted to bring out the meaning or emotion within the stories he tells. Most consider his music to be country, folk, folk-rock or Americana. His songs have been recorded by numerous others over the years. Perhaps his best known or most popular songs are Brand New Tennessee Waltz, Biloxi and Mississippi you’re On My Mind. Winchester became a force against the Vietnam war in the 1960's and 70's. He also became close friends with Robbie Robertson of the Band, who help promote and produce some of his music. His voice is the perfect match to his songwriting, as he has a way of expressing the depth of the music through his singing.


In this song, If I Were Free, he sings about his love for someone with aching wisdom (and much wisdom is aching; truth and beauty are not always easy). Here is an example from the third verse of the song:


If I were wise, then I would see

What makes you love

a foolish man like me

I'd stand by you, just like a tree

Oh, I know that's what I would do

I would chain myself to you

I would never leave this room

if I were free


The genius of this song, is that Winchester says so much without saying the actual truth, since the truth can often hurt so we often leave it unsaid. as a psychologist, I learned to listen for what is not said as well as to what is. Both matter. The refrain of this gentle song is always "If I were free." But he never really says what it is that prevents his full freedom. For me, this is so often the way life is. We are all restrained by dynamics both within our beings and in the world we live in at any time. Externally, there are always things such as social differences, economic traps and beliefs, political differences, religious differences, age, gender, distance, family that can keep people apart. These divides that leave us lonely and alienated, sometimes even from those we deeply love. So much heartbreak in this old world and in how we approach living in it.


But there are also countless internal traps that hold us at bay or leave us adrift. Often, these are developmental in the course of our lives and we cannot see or understand what these chains even are. Trauma that leaves us fearful, even of love which is the most vulnerable thing of all, or that has left us with the belief that we are defective and cannot love or be loved. Distrust left over from other heartbreaks or betrayals, fears of judgements or rejection from others; depression that ravages our mind and body, illnesses that leave us bound, to only name a few of these inner hauntings. What this song is about, but masterfully left unsaid and thus given even a more powerful voice are all of these sources that limit the freedom of our lives and diminish health and peace and often foster projection of these ghosts onto others with viciousness and violence, perpetuating the very sources of our own distress in the lives of others, ironically damaging the lives especially of those most loved by us or closest to us, and so the circle of life, damaged thought it may be get passed along.


I have always understood my motives for becoming a psychologist in this framework. I tried to spend my working life offering help to those haunted and bound by such distress, disease and social injustice. People often ask me how I could be with people who are so hurt and experience such sadness with them and I have always had two answers. First, what an honor it is to have the trust of others to be with them in the fullness of their sorrows and hopes; to witness such courage. Second, most people gain some significant measure of freedom and healing through their therapy and to also witness and share in these steps and stories of change; in their recovered or new found responsibility, brilliance and joy is a reward I could never repay. As Winchester sings, "I would never run again if I were free."




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