It will be 19 years next July since Leonard fought his way into a three-man play-off with Frenchman Jean Van de Velde and eventual champion, Scotland’s Paul Lawrie.
Leonard, now aged 45, made his Open Championship debut in 1993 at Royal St. Georges as the then U.S. Amateur Champion.
Four years later, Leonard won the 1997 Open at Royal Troon and after all the official functions celebrated in darkness on the 18th green enjoying a pizza, a beer and a cigar.
Then at Carnoustie in 1999 Leonard was five shots adrift of Van de Velde heading into the final round and produced a one-over par 72 to eventually tie Van de Velde and Lawrie who had come from 10 shots back and shoot a 67.
The trio each hit poor drives down the first of the four-hole aggregate play-off with Leonard and Lawrie taking bogeys and Van de Velde a double-bogey.
All three missed the second green and took bogeys with Lawrie and Van de Velde then birding the third extra hole and Leonard par.
It gave Lawrie a one-shot lead heading down 18th for a second time that day and with the Scot hitting a career-defining 4-iron to four feet for birdie for a three-shot victory after Leonard had found the Barrie Burn for bogey and Van de Velde the rough also on route for bogey.
Leonard returned to Carnoustie in 2007 only to miss the cut but after sharing eighth in 2009 the Texan has missed six cuts in his last seven Open Championships cuts since 2010.
Instead the American is looking forward in returning to Carnoustie next July without his golf clubs and as a member of the NBC TV reporting team.
“All throughout my career, I have looked forward to heading over there to tee-up in The Open and I also have great memories of Carnoustie,” he said.
“Though in saying that, I am looking forward to going back next year and not playing (smiling) because it is so darn hard competing in an Open.
“I went to Royal Birkdale last year but it no longer excites to practice for a couple of weeks and to go over there and shoot a couple of 78s.
“It just not fun to me but I am now really enjoying being behind a microphone and bringing some of my experiences of playing in The Open so many times to those watching TV coverage of golf.
“It is where I see my value as a commentator as I have been there and done it, and very proud to say I’ve won an Open Championship and also competed at so many of The Open venues.”
Leonard was commenting after contesting last week’s Father-and-Son Challenge in Orlando where he made his debut in the event alongside his 77-year old father, Larry.
And Larry was asked if he had drunk out of the Claret Jug his son won at Royal Troon.
“Have I drunk out of it? A better question would be what I haven’t drunk out of it,” he said laughing.