Sailorman Jack

I’ve been privileged to know a lot of crazy people in my lifetime. One of the craziest was Sailorman Jack.

When my first wife and I moved back to the USA from Belgium in 1976 we decided to take up residence in New York City. NYC was dirtier and more dangerous in those days than it is today (which may be debatable), but apartment rents in Manhattan were still higher than in most places and the job market was tighter. Having had some success with my recording career in Europe, I’d hoped to use that to my advantage in The States, but ’76 was the first year record companies began to see a decrease in their sales so most had put a freeze on signing new artists. And frankly, I just wasn’t that good of a musician.

So with that hope dashed I fell back upon generating a source of income in a way I’d hoped I’d never had to again: teaching guitar. I’d hit a rather novel way of recruiting students by how I’d advertise what I was offering, creating an ad with copy positioned against a background of music staves and shouting in boldfaced capital letters FIRST LESSON FREE! Beneath that were a few paragraphs briefly describing my background and instructional technique. At the bottom were telephone number tear-off tags. I’d print these ads up for about a nickel a page at a local copy shop then paper the town.

Before I knew it the phone began to ring and I built a thriving little cottage industry from my overpriced cracker box sized Upper Eastside apartment. Through this reasonably lucrative little endeavor, I met the two guys who would later become business partners in my entertainment promotion and marketing company, as well as my lawyer, my second wife, and a few friends. It also opened the door for a career-changing internship at PolyGram Records as well a less career-changing internship assisting as a psychotherapist/hypnotherapist, but that’s another story altogether. Last, but not least, it led to meeting one of the zaniest characters I’ve ever known, the legendary Sailorman Jack.

Jack, before he had even become Sailorman Jack and was still only Lawrence Kobacs, came in for his free lesson and told me he wanted to learn sea shanties. So I taught him how to tune his guitar and the chords for “Blow the Man Down”. After his lesson, I did some research as to what sea shanties were and then would teach him one each time he returned as a paying student. Turns out those sea shanties were the songs sailors sang while they worked aboard ships at sea. Whenever a job aboard a 19^th century vessel was large enough that it required multiple able bodies to perform, a shantyman would begin singing a shanty so the others could coordinate their muscular efforts in unison by following the rhythmic pattern set by the music. In other words, they were seafaring work songs. 

Sea shanties were usually lyrically rude, crude, off-color, and full of sexual innuendo regarding what the crew would do not only with the captain’s daughter but the captain himself, as well as the first mate, prostitutes in ports of call, or other individuals in faraway places old tars would likely encounter during their travels upon the seven seas. A few I still recall had titles like “Friggin’ In The Riggin’”, “Maid of Amsterdam”, “What Do You Do With A Drunken Sailor?”, “Haul Away, Joe”, and “Spanish Ladies” among many others.

After learning one of these cheeky chestnuts he’d pay me for the lesson (if memory serves me well I think I charged $5 for a one-hour session, which I thought was pretty good considering that was almost double the federal minimum wage of that era) and book another appointment for the following week. After mastering a new tawdry tune he’d let out a hearty shout of “Huzzah!” Each time we met he appeared to add a new article of attire and/or mannerism that referenced the look, language, and dress of a 19^th- century seaman. Thus, Mr. Kobacs began sporting bushy muttonchops sideburns and a large waxed handlebar mustache. Next, there was a Sherlock Holmes-style meerschaum pipe, the captain’s cap, a large pocket watch attached to a fob that dangled from his trousers, and naval blazer adorned with military medals and ribbons.

One day he announced he’d begun busking (playing music for tips from those passing by) on the NYC subway platforms and had adopted the pseudonym of Sailorman Jack when performing. Many of his impromptu platform performances were interrupted by run-ins with NYPD cops who told him if he didn’t pack it up and leave they’d either have to write him a ticket or take him in for an arrest. To this he’d respectfully respond to the man in blue that he knew the officer was only doing his duty, thank him for his service, and invite him to join him for a beer; an invitation that some accepted. Sailorman Jack soon had a collection of friendly drinking buddies from precincts all across The Big Apple, many of whom would turn a blind eye when they discovered him again singing his shanties in the subway and a few who would even sing along on the choruses of some of his salacious songs.

But soon the subways were no longer a large enough stage for this larger than life lunatic so he began booking shows in local clubs in Greenwich Village. Jack asked if he could hire me to put together and play in a back-up band for these shows, so I told him as long as he’d pay me I’d be happy to join him in his insanity. Mike, one of my other students at that time, and who would later become my friend, attorney, and co-founder of one of my future businesses, I recruited as part of the act now known as SAILORMAN JACK & HIS SALTY SEAMEN. We backed Jack’s guitar and voice by trading off on guitars, bass, concertina, harmonica, tambourine, washboard, spoons, jaw harp, kazoos, and various other sources of sound as we gigged about town. So he could sell cassette tapes of his music at the shows Sailorman would also book us to work with him in recording sessions. To my delight, we actually ended up making some pretty good albums. An added plus was it was the first time I was actually paid to produce records, and years later led to working in the studio with some very notable acts.

The funny thing was even with those stage shows at night Jack would still hit the subways to busk during the day. It was around that time New York Mayor Ed Koch was up for reelection and was putting pressure on the Manhattan Transit Authority to clean up their act and make improvements on the way they ran things beneath the city streets. So what did the MTA do? They commenced cracking down on those performing at the subway stations instead of improving service, cleaning up the trains, or providing better security to combat the crime that ran rampant underground.

Now, this move by the MTA really pissed off Sailorman Jack. So what did he do? He decided to run against Mayor Koch in the upcoming election. Mike, the lawyer, and I helped him form the Third Rail Party whose only plank in its platform (get it?) was to make subway service free for all riders. Past studies had concluded that the MTA was hemorrhaging so much money in the way it managed the token booths and turnstiles that fewer tax subsidies would be needed if it simply laid off the workers responsible for the turnstiles and working in the booths. Don’t believe me? Just Google it!

Once Mike had registered our Third Rail Party with officials Jack asked me to help him write a campaign song, book some studio time and assemble the SALTY SEAMEN to record “Dirty Ol’ Train”. I sent it out, along with a press release, to multiple media targets throughout the metropolitan area. Before you could say “All hands on deck!” newspapers like the New York Times and network morning talk shows were providing a fair amount of coverage for us. Jack would speak on those television broadcasts about his Third Rail Party subway platform and then we’d perform the song. Everyone from Imus in the Morning to The Howard Stern Show wanted to have us on their radio programs.

We made quite an impact, but of course, we lost the election. Afterward, I went on to write an unpublished book about it called “The Once and Future Mayor of the Underground”, and to launch several successful companies. Mike eventually moved to Florida to raise a family, and Sailorman Jack just simply disappeared from the spotlight. Years later, probably around 2010, some mutual friends told me they heard he’d moved to Ohio to form a pipe and tobacco collective. Shortly thereafter I received an anonymously sent envelope that contained only a clipping of a recent newspaper obituary. Sailorman Jack had died.

Of all the songs I produced and recorded with Jack, my favorite was “Fiddler’s Green”. It tells a story of an old salt who knows he’s knocking on death’s door and implores a fellow mariner to wrap him up in his oilskins and jumper and to just tell his old shipmates he’s taking a trip to that place where worn-out seafarers are eventually destined to go. So, I know if I don’t end up in hell one day I’ll surely meet up with Sailorman Jack again where the weather is clear and the dolphins do play. Where’s that you ask? Well, as any swab worth his daily ration of rum could tell you, of course, that would be Fiddler’s Green. Until then Captain, keep your eyes on the horizon, the wind in your sails, and smooth sailing.