Tommy the Limo Driver

A couple of weeks ago I attended a software conference in Naples, Florida with the president of our company. We arranged a car service to take us from the conference back to the airport, Tommy’s Limo Service. Leah, a colleague, asked how we were getting to the airport and I said “Tommy.”

“Oh, you’ll like him. He has been sober for 25 years.”

“Leah, how the heck would you know that?”

So I was slightly worried that Tommy was going to be extremely chatty and way too eager to monologue our way to the airport. We have all been there, trapped for 45 minutes quickly running out of “uh huh’s” and other marginally polite ways to acknowledge and feign interest. But I could not have been more wrong. We were the ones that soon were asking question after question.

Tommy started slowly with comments about the feral pig situation near the Naples airport but that led to him telling us that his home was the equivalent of a petting zoo with 16 rescue dogs, a small donkey named Obama, a miniature horse named Romney, a raft of macaws and other parrots, and on and on.

“That is great that you do that much rescue. How long does it take to feed all your animals?”

“About two hours although it could take all day, you know what I mean? There is always something that needs to be done. Plus, my wife and I can’t really leave and go anywhere with all the animals at home. The Lord blessed us with really good neighbors, someone new moved in recently and I was really worried but she told me she thought it was great what we were doing. Even though we are in the country and have five acres there is still a hell of a racket.”

“Tommy, do you have any help?”

“Well, I had a guy who just got his ass handed to him when the economy tanked — good guy — and I told him he could live on my farm. This guy can fix anything so I told him he could fix up the barn, make a living area, and I’d pay for the materials. I thought he was going to do it but he didn’t. But about a month after that he said, ‘Tommy, I got a great guy for you. You won’t have to pay him anything, he’s got a shit little trailer, let him fix up the barn and live there and he’ll help you out. He can do everything, electrical, plumbing, carpentry, plus he likes animals.’

So I am thinking that is sounding pretty good. But then he says there is only one catch; he just got out of prison after 30 years. He shot at a cop. He was a dumb ass kid, he was drunk. He is really smart but I don’t think he got past the first grade. But he paid his debt. So I say, what the Hell, what’s his name?


So I have to tell my wife that a convict who was in prison for 30 years for shooting at a cop is going to be living in our barn. That did not go over too well, I can tell you that. She talks to her brother, who is also named Tommy, kind of funny, and he is a minister and he says to my wife ‘this will not end well’ so she comes back from talking to him and wants Sheldon gone.

I gotta tell you that really pissed me off. The God that I know is a God of second chances. I put my foot down and told her, ‘Sheldon is not going anywhere. I’m not moving on this.'”

“Did she ever get over that, did she start to like Sheldon?”

“Oh yeah, after a month or two she got over it. Plus, she was always after me to get help and now I have help. Sheldon doesn’t drink and he doesn’t smoke any of my pot I can tell you that.”

That kind of surprised me because Tommy was not a young man, somewhere in his sixties I would guess, but before I could give that much thought he went on.

“There is one thing about Sheldon, though; he likes to wear women’s underwear.”

“That doesn’t sound too bad but how exactly do you know that?”

Tommy laughed, “Sheldon is not gay but I came outside one day and he had all of these women’s thongs on his clothesline, all wild colors. I said, ‘goddammit Sheldon, I have people coming over – take down your damn thongs.’”

“So you’re sure they were his?”

“Well, one thing I should explain: Tommy thinks of himself as a woman in a man’s body. I guess he is a lesbian because he has a girlfriend and they dress up together and shit. He occasionally calls himself Jeanette. I once paid him $600 for something special he did, I can’t even remember what it was now, and he took $400 of that and bought a white wedding dress. I don’t care, you understand, his business is his business. I do have to yell at him sometimes to take off his falsies.”

“Tommy, Sheldon wears falsies?”

“Yeah, when we get to the light I’ll show you a picture on my phone. I have to yell at him, ’Sheldon, take off your damn tits, I got people coming over!’ But if he has done something really good, like fixes something we didn’t think he could, he would put them on and wear them around because he knows I won’t say anything. He knows he earned it.”

Tommy reaches around and shows us the photo of Sheldon on his iPhone. Not in a mocking or a demeaning way but with the same enthusiasm he has for things he cares about, like his giant talking parrot, his Presidential donkey, his rescued, half-wild wolf bred with a mastiff that almost took out a Doberman until Tommy intervened. So, there is Sheldon looking goofy and happy in a white T with an excellent rack and arms that look like they have pumped a lot of iron.

No matter who you are, when you go to prison you are not the same when you bounce out some 30 years later. If this is how Sheldon/Jeanette stayed sane, more power to him. But especially more power to Tommy, who is guided by his God, a God of second chances. That stayed with me. What would Jesus do? My guess is that he would happily have Sheldon in his falsies help Tommy take care of his flock.

2 thoughts on “Tommy the Limo Driver

  1. I might have a picture of Sheldon on my phone, courtesy of your travel companion. I laughed just as hard, if not harder, while reading this as I did when Sheldon and I were first introduced. (And you wonder why I wanted to attend the conference…silly you.)

  2. A great story. If you are ever asked to give a sermon – and if you can bring yourself to clean up the language just a bit – you have one ready-made. Congratulations!

Leave a Reply

Your email address will not be published.