Jay Hershoff is a negotiator. As the founding partner of Hershoff, Lupino and Yagel his job is to negotiate family disputes and the culpability of those accused of a crime. Some 25 years ago he negotiated a $22 million deal with Baptist Health of South Florida to construct Mariners Hospital and just last summer inked his signature on a document that essentially saved Fishermen’s Hospital. As a director for First State Bank he has a front row seat to some of the biggest business deals in the Keys and he even successfully negotiated a hostage situation when his ex-wife took the keys to his ‘76 Porsche 911s, Targa.

A son of a plumber who graduated 12 out of 13 from Villanova’s school of economics, Hershoff was seduced by South Florida and earned his law degree from the University of Miami before embarking on a legal career that has spanned nearly five decades and taken him halfway around the world.

How does a recent college graduate from Baltimore with only $17 in his pocket end up in South Florida? In the middle of my senior year (’64), on Christmas vacation, two guys from school and myself drove to Miami in a Volkswagen. When I went back ten days later I had been to the Fontainebleau to see a show. I can’t remember who it was, maybe it was Frank Sinatra. I had been deep sea fishing. I had been to Jai Alai. I had been water skiing. I had been out to dinner. I had been to the dog track and when I got back to Philadelphia I had $50 in my pocket.

How did you explain this to your father – a plumber struggling with his business? So I said to my father, ‘That is the promised land. I am going to Miami and I am going to try and get into law school in Miami. If I can go down there, knowing nothing, and have the time of my life with no money and come back with more than what I started with, that is the place for me.’ He said, ‘What are you going to do if you don’t get into law school?’ I told him, ‘I am going anyway.’

What was Miami like for a young lawyer back in the late ’60s, early ’70s? I was pretty naïve back then. I thought Miami was the promised land – and it was. It was great. And it was crazy in those days. I would get called out in the middle of the night when the Sheriff’s Office went on a raid – especially for Bolita – Cuban numbers. We had clients that were involved in it. The guy I worked for was on the payroll for the CIA so whenever any of their informants got in trouble they would call him and he would represent them. There was always somebody in trouble. The government had the biggest scums on the planet working for them.

Any crazy stories that you can share with us? I had a friend murdered by the cartel in his law office one morning. Turns out they were after his partner and it was a mix-up. I had other friends from law school who went to prison for 15 years. All the judges were involved that I worked in front of. They were fixing trials and taking money. It was horrible.

How did you manage to avoid all that? I didn’t get involved!

What prompted you to establish an office in the Florida Keys? I had been coming down on weekends throughout the ’80s. People would show up at my house with bags of cash. Everybody was paranoid. Everyone was smuggling and everyone was in trouble. Except everyone I represented somehow got off. My wife didn’t want bags of money coming to the house, so I met with a part-time lawyer named Barry Segel back on Hood Ave. I said, ‘Barry, I don’t want to go back. Can I rent your office on Monday?’

One of the first deals you negotiated for Mariners almost doomed the hospital when it became apparent the developer wasn’t able to perform or meet the construction budget and a lawsuit was filed. How did you bring the hospital out of it? We were in the middle of the board meeting when the Baptist board chairman Bob Cole called. On the phone I said to him, ‘I am in a lawsuit and I am in charge of the community’s money. I want to know: if I settle this lawsuit are you gonna build our hospital?’ He said, ‘Mr. Hershoff, you are a lawyer and know I cannot give you that assurance. You are just going to have to figure this out and get it resolved.’ ‘Mr. Cole,’ I said. ‘If I were one of your sons and I came and asked you, what would you tell me?’ ‘Mr. Hershoff, it would depend which one of my sons asked,’ said Cole. Everyone cracked up and laughed and I said ‘Mr. Cole, thank you. You have just given me my answer.’ I settled the lawsuit over lunch at Ocean Reef and then Baptist built us a hospital for $22 million. I also convinced them to put the Tassel Building up before the development agreement expired.

The last 24 months have been a very busy time for you, leading the negotiations for Baptist to acquire Fishermen’s Hospital. Any ‘proud papa’ moments? I found out they didn’t have enough money to make payroll on a Friday. I got Baptist to give Fishermen’s a $3 million line of credit to make sure the doors stayed open. They had never done that without going through a whole process with analysis and committee. We got that done in a week and a half to keep the doors open right before we assumed ownership.

Why are you so passionate about the hospital? My life changed by living here. I have had a good life here. Honestly I didn’t do much in terms of civic stuff before I got here and got involved with the hospital. Now it’s a passion to make sure I do something to help other people. I have really been fortunate. I appreciate it and I enjoy it.

What’s your favorite place to eat? Ziggy’s.

You are a car guy. How many vehicles are in your driveway right now? Five, including a Mercedes convertible and a Jaguar XKR coupe. But there may only be four tomorrow. I am always looking at cars.

Has your life ever been in danger? Yes, but I really can’t talk about that.

If you can have drinks with anyone alive or dead who would it be? This is going to sound crazy. I would love to have drinks with Diane Keaton. I don’t know why. I just like her movies and what she stands for. She seems to be an interesting lady to have a drink with. But seriously, Barack Obama.

What would your current and former law firm partners say about you? That’s an easy one. ‘He made us a lot of money.’

What are the chances Rob Stober gets his name on the letterhead? I defer to Russ and Jim.

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