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Life Lessons of a Legend

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Life Lessons is a dramatic and inspiring story of Captain Tony Tarracino's remarkable journey from the ghettos of Elizabeth, N.J. to becoming a living legend serving as the Mayor Emeritus of Key West. He made a career of being a mesmerizing storyteller, captivating personality, and Casanova of the sea. The Captain swears like a sailor on leave yet speaks of compassion as the word we should all live by. In Life Lessons you learn of his harrowing life on the sea, secret spy exploits as a gunrunner during the Cuban revolution, tales of the oldest bar in Florida - Captain Tony's Saloon, being immortalized by his friend Jimmy Buffett in the song Last Mango in Paris, and Tony's family of 13 children with eight different women. Life Lessons captures the legendary tales and riveting lessons learned from a life of great adventure lived on the edge.

358 pages, Paperback

First published September 26, 2008

6 people are currently reading
152 people want to read

About the author

Brad Manard

14 books

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5 stars
40 (40%)
4 stars
27 (27%)
3 stars
22 (22%)
2 stars
9 (9%)
1 star
2 (2%)
Displaying 1 - 26 of 26 reviews
Profile Image for Kirk Coco.
136 reviews1 follower
May 17, 2015
The amazing life of Captain Tony would certainly make a great book and movie. Unfortunately, it made a B-movie and then this poorly written and ABYSMALLY edited book. If you can suffer through the constant changes in tense and spelling errors, get past the 1950's Leave it to Beaver life the author must have read up to this point and the word "compassion" being clubbed repeatedly into the reader's skull, you might get a little bit of the amazing character who was known to many as Capt. Tony.
Profile Image for Chris.
1 review
July 22, 2019
Gave the book 3 stars because a third of the book is about Captn Tony, a third of the book is about the author and a third is BS (one for each). Overall, a good book and lots of neat historical stories. I am just not sure how much truth are in some of the stories. "Life Lessons" is an appropriate title.
Profile Image for Brad Manard.
Author 14 books
June 23, 2012
Having not been to Key West or familiar with Capt. Tony - or Jimmy Buffett for that matter, I read Life Lessons because I know the author. Not knowing what to expect, I found the writing fluid and fun. The story is both engaging and filled with thought provoking lessons from a true man of the past with a vision on the future. I never met Tony and in learning his history, I was at first skeptical, then intrigued, and finally, as Tony did in real live, drawn in and fascinated. From reading Life Lessons, I grew to think of him as a friend, one that I missed knowing, a person that would have enriched my life in person and did so through this book. If you have a playful spirit and a sense of adventure, along with a desire to have a positive impact on the world, I highly recommend reading Brad's book. Carolyn Clark
Profile Image for Kody Swencki.
65 reviews
January 3, 2026
I picked this book up in Captain Tony's while on vacation and I'm glad I did. Key West is a special place that my Fiancée and I instantly fell in love with so many years ago. This is something we have in common with both Captain Tony and Hemingway. The difference is, Captain Tony decided to stay and create a life we all dream of. This tells his story in all it's glory for better and for worse. While he was a flawed man with adulterous tendencies, no one can dispute his compassion for people and his love for life. He truly lived it to the fullest and created the legend that is his namesake. I would rate this a 5/5 but it was very repetitive in some chapters which slowed the pacing. Overall, worth the read to get to know an interesting Key West icon.
Profile Image for Randal Wallace.
27 reviews
February 13, 2025
I found this to be a fun book to read. Captain Tony’s life stories are exciting & his life philosophy is a good piece of advice to live by. The book is flows well & I thought a great first effort for the author.
That all said he does use the word compassion & find the jewel & say a kind word way to much. That was said so much it made you wonder if he wrote the book with gaps in the time he put in it and had forgotten he had already made that point. Overall though it’s a really good book and I recommend it for everyone especially if you’re like me and love the Florida Keys and Key West
Profile Image for Marla Upshaw.
42 reviews
May 30, 2023
I rarely ever read memoirs, biographies, etc...but as a lover of Key West, and especially Captain Tony's Bar (always our first stop in KW), I just had to read this. Wow! What a life lived to the fullest and his Life Lessons ... So much wisdom there. I highly recommend this book...a bit shocking, a load of smiles and a few tears...it's definitely worth the read.
Profile Image for Debbie Stanley.
145 reviews
February 9, 2019
This is an awesome story! I don’t think I’ve ever read a book that has made me feel this good! I didn’t want to read the last chapter because I didn’t want the book to end. I only wish I could have met this amazing man - Captain Tony Tarrasino.
2 reviews
May 19, 2020
Worth reading if you have an affinity with Key West and Captain Tony. The author’s repetitive use of the word “compassion” and phrase “find the jewel” was nauseating. The book was about 100 pages too long. However, it was interesting to hear the stories of Captain Tony and the history of Key West.
Profile Image for Nic Schuck.
Author 6 books23 followers
December 22, 2019
It was cute. Would’ve liked it better as a biography. Too much about the writer that I wasn’t very interested in.
Profile Image for Joe.
433 reviews
Read
November 27, 2020
Excellent. Awesome tail of a man who lived a life that some only dream of. Well written.
5 reviews
April 14, 2025
amazing lessons from an unexpected source
Profile Image for Al C.
11 reviews
November 15, 2025
This book seemed to be more about the author than it was about Captain Tony.
Hoping for an actual book about Captain Tony someday…
Profile Image for Cap'n Bobby.
5 reviews
March 30, 2013
I would recommend this book to anyone, especially to people who have an interest in Key West, Jimmy Buffett, or Captain Tony. I wasn't sure how I was going to feel about the book, a book written about a man, Capt. Tony, who had a reputation as a womanizer, gun runner, gambler, etc. Strangely, the message of the book was very spiritual, very Christian, very Buddhist, that life is about people. Treat people with compassion, find the jewel in people, always offer a kind word. It takes no longer to build someone up than it does to tear them down, so build them up. Since I have read the book, I find myself resisting my inclinations toward judgment and trying to act more compassionately. As such, this book affected me more than most books I have read, and, for that reason, I recommend it to you highly.

For those of you who love Key West, the book will remind you of your trips to the end of the road. You will find yourself visualizing the island, a mental and emotional return to the southernmost city. For those of you who are Buffett fans, there are plenty of Buffett references and several intriguing stories about the mayor of Margaritaville. The book also shows what one man, Capt. Tony, did with his life, thus implying what anyone can do with his or her life.

The book, however, does have some flaws. It's a book about Capt. Tony, but the author, Manard, at times comes off as a bigger Buffett fan than a Capt. Tony fan. Manard is not a great writer yet. There are moments when the story suffers from stylistic choices the author has made. For example, the author inserts narration into dialogue in manners that get in the way. In other words, there are times in which the author should have cut off all narration and just let Tony speak. It is Tony's voice that makes this read memorable, not the author's.

Cap'n Bobby
Profile Image for Andrea Bastien .
78 reviews
April 11, 2019
As an amateur book collector, I was irresistibly drawn to a book sold in a Key West tavern. It may be the only place I’ve never bought a book from, and i was happy to spot and purchase this story. In many ways this was the perfect read for a vacation in the Keys. Reading about the life and stories of captain tony was like reading a history of Key West itself. That being said, the narrators particular style of telling and retelling, of intertwining his story with Captain Tony’s was not my favorite. It was genuine, but the framing of his perspective around Captain Tony’s seemed almost apologetic, as if he was more concerned with how the world would see Captain Tony than how Captain Tony told his story. The story is incredible, the character comes alive, and no apologies are necessary.
Profile Image for Dan.
44 reviews
September 17, 2012
A gambler on the run from the New York Mob, a boat captain, bar owner, gun runner for the CIA into Castro's Cuba, Mayor of Key West and on top of all that, he fathered 13 children from 8 different women. We Captain Tony died at the young age of 92 his oldest sone was 72 his youngest was 20. The very true story of Captain Tony. The owner of Captain Tonys Saloon in Key West and the subject of Jimmy Buffett's song, "Last Mango in Paris." Not really a page turner and the first book by the author, but I enjoyed it immensely. I read the bulk of it on an airplane going to and from home. Key West is a truly wonderful place to visit and Captain Tony is part of the islands history and flair.
1 review
July 12, 2014
I must tell you, the book was not what I expected, not at all. I was thinking I would read a quick biography on the man, myth, and legend. I was surprised at how you unfolded the life of a complicated man and made his life mission so simple to understand and implement. Every time I would read a chapter you placed me exactly at certain points on the Island that I know all too well. Having local knowledge of Key West makes this read that much more rich in my opinion. I really enjoyed the way you two developed a friendship that changed both of your lives forever. The story telling is fabulous and when I finished it this morning it left me wanting more.
Profile Image for Mickey Asteriou.
Author 11 books3 followers
June 17, 2013
What we have here is an ethical conundrum. The book's refrain is to show compassion, to share a word of kindness. So, do we follow this advice and concentrate on the fascinating tales of Captain Tony themselves; or do we fixate on the awkward, forced writing and the embarrassing amount of spelling and grammar errors? At book's end, you have to ask yourself: are you the kind of person who can find the jewel in this book and give it five stars, or are you going to be an a-hole and give it two.
314 reviews18 followers
January 15, 2013

The story is both engaging and filled with thought provoking lessons from a man of the past with a vision on the future. I have never met Tony and in learning his history, I was at first skeptical, then intrigued, and finally, as Tony did in real live, drawn in and fascinated.


Won on goodreads.
Profile Image for Tami.
67 reviews
November 30, 2010
Glad I read it because it was on my list. Writing 'style' drove me crazy, and the book itself - well, never mind. Lots of people love it & thats great. I'm not one of them, so I'll stick with 'if you can't say something nice, don't say anything at all . . .'
23 reviews
September 17, 2009
"I went down to Captain Tony's..." The beginning of the famouse 'Last Mango in Paris' Jimmy Buffett song resulted in one fan, now author, to write a book about Tony's adventures and advise. A good quick summer beach read.
Profile Image for Marty Hughes.
31 reviews
December 28, 2010
Good book on a legend that we will miss. I met Captain Tony in his old bar a few years ago. I was complaining out loud that the shot glass prices were too high. Captain Tony sitting over on a stool out of my sight lowered his cigarette and said, "Seven dollars is a little high".
Profile Image for Caitlin.
7 reviews1 follower
January 26, 2016
As a huge fan of Key West,this has become my all time favorite book. This book makes you look at yourself and your relationships with others. Captain Tony was a big proponent of compassion and his message is clear in this book.
Profile Image for Kris.
53 reviews
August 3, 2011
Great book about a Great man. Had the pleasure of meeting him twice.... Bad rep, but a wonderful and hopeful heart...
Profile Image for Darby.
34 reviews1 follower
September 11, 2012
Terrible writing on a great subject.I found spelling or grammatical errors on nearly every page, it seemed. It distracted from what should have been a fantastic story.
Profile Image for Debbie Burgess-Shaw.
46 reviews
February 22, 2016
The author knew Captain Tony well. He created a human story about an island legend. Did not enjoy the writing as much as I loved the story.
Displaying 1 - 26 of 26 reviews

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