He entered the 2011 general election as a young apprentice jockey and led his party to a humiliating defeat. To compound his misery, he had to grin and bear it while the then champion jockey referred to him as her "little son".
Fast-forward to 2016 and he entered the starting gates once again, this time as a seasoned rider who had come through a bruising internal election, survived many attempts to undermine him, and determined to win, although the bookmakers gave him only an outside chance.
But when the dust cleared on February 25, 2016, it was Andrew Michael Holness who had led his Jamaica Labour Party (JLP) to victory, albeit by the narrowest of margins, and a new champion jockey was crowned.
"He did the nearly politically impossible by leading his party to victory in the general election and convincing the people with the crafting of proposals he put on the table," said attorney-at-law and talk-show host Emily Shields.
Holness would again face the starter months later on November 28, 2016 in a local government election, and this time the victory was more emphatic, even though there were stewards enquiries and protests lodged by members of the vanquished People's National Party (PNP).
Before the curtain closed on the year, the former champion jockey, Portia Simpson Miller, finally admitted that she had run her last race while her "little son" was comfortably in the saddle of the JLP.
In the lead-up to the general election, Holness captured the attention of the media as he defended himself over allegations surrounding the house he was building in upper St Andrew, and outlined a strategy to convince Jamaicans to give him a second chance as prime minister.
After the election, it was all Holness as the nation waited on the announcement of his Cabinet ministers, then the wait was for the first budget crafted by his administration, after that it was the wait for his plan to deal with the International Monetary Fund and all the other issues faced by a new prime minister.
These ensured that Holness was almost a constant in the media, including online and social media, whether the news was good or bad.
For these reasons, he has emerged the clear news maker of the year, with leading members of the local media fraternity agreeing that while athletics icon Usain Bolt must be a consideration, it is hard to top Holness as the person who most dominated the newscasts last year.
"I have to agree that Prime Minister Andrew Holness has been in the news a significant number of times, positively and negatively, in 2016," said veteran journalist David Geddes.
According to Geddes, while the impact of Simpson Miller's announcement that she would not seek to continue as the PNP's president would make her a contender for news maker of the year, the number of times that Holness has been in the news would make him the winner.
"I think this would have redounded to the administration's benefit more though, if he had managed to have a few press briefings. I also believe that in 2017 the Holness administration will launch a comprehensive public relations plan, and this will be designed to convince people that they should be allowed a second term," said Geddes.
For another veteran journalist and broadcaster, Fae Ellington, the exploits of Bolt at the Olympic Games, and the number of news stories written about him before and after the games, make him a strong contender for the 2016 news maker of the year award. But Ellington agrees that the stories about Holness, complimentary or otherwise, could give him the edge.
"Throughout the year, Prime Minister Holness was constantly in the news for all kinds of things, and of course after February 25, it was very obvious why he would remain in the news," said Ellington.
"Overall, maybe it would be right to select Andrew Holness as the news maker for 2016," added Ellington.
Shields has no doubt that at 44 years old and in his second stint as prime minister, Holness was the news maker of the year for 2016.
She pointed to several news stories involving Holness over last year.
"Like the naming of the Economic Growth Council, though we haven't seen the manifestations yet, but I think it's a fantastic idea to be talking growth with an IMF agreement in place, and he has put a number of people around him, like Dr Nigel Clarke and the naming of Major General Anthony Anderson as national security adviser, that shows that he recognises that the crime problem is major.
"For the most part he has been in the news for positive matters, and the negative ones that have been there he has managed to contain them, so I would agree that he is the news person of the year for 2016," added Shields.
For news director Franklyn McKnight, Holness is the news maker of the year by virtue of his office as prime minister and what that platform allows.
"Then there are the forums, and the significant public relations apparatus he has. He has been making announcements that will have to be addressed sooner or later, and for that he remains in the news. Not for anything extraordinarily significant, but because of his office," said McKnight.
He pointed to other major news makers, including Tourism Minister Edmund Bartlett, "who is probably in the news more than the prime minister".
According to McKnight: "There is also Dennis Chung, in the news significantly for many reasons, and in particular about the National Solid Waste Management Authority. But the outgoing PNP leader has also been in the news; she made Holness the news maker. She has come off negatively in many ways. She looked bad and sounded bad, in comments after the elections."