He was arrested for failing to attend court for a traffic summons last year, and served four days in detention after being charged by the Singapore Police Force in 2013 for going absent without official leave (AWOL) to play in a Malaysia Super League (MSL) match.
Released by Tampines Rovers at the end of the 2017 S-League season for disciplinary issues according to then Stags coach Jurgen Raab, national left-back Shakir Hamzah could have easily turned out to be one of those talented footballers who strayed and never got to fulfil their potential.
But, thankfully for the 26-year-old, he came to his senses before it was too late.
After a solid season in which he played 21 Singapore Premier League and 10 AFC Cup games - Shakir missed five matches only through injury and suspension - and scored four goals for Home United, the indefatigable defender's energetic displays have been rewarded with a one-year contract with MSL side Kedah, his first with a foreign side, and a pay rise.
Before he leaves for Alor Setar with his wife, two daughters aged two and one, and a two-month-old son on Thursday, The Straits Times caught up with Shakir on Saturday.
He shared how he decided to turn over a new leaf only when he was restrained by cable tie during last year's arrest at Changi Airport, right before his former club Tampines departed to play pre-season friendlies in Terengganu.
He said: "I forgot about my court date. Later, I was released on bail after about one hour in the station but, in that time, I realised it was time for me to become a better person.
CHANGE FOR GOOD
I see talented players like Mario Balotelli who are so good but got nowhere in their careers. If I have a similar heck-care attitude, I won't go far, and I feel I can still improve to become a better footballer.
SHAKIR HAMZAH, on his decision to turn over a new leaf and be serious about football.
"I see talented players like Mario Balotelli who are so good but got nowhere in their careers. If I have a similar heck-care attitude, I won't go far, and I feel I can still improve to become a better footballer."
There was also speculation that Shakir was going through some relationship problems, but he insisted that his 29-year-old wife Erni Maulood and father Hamzah Haron are key to his turnaround.
He said: "They had been scolding and reminding me that if I continued to be ill-disciplined, how could I further my career?
"In every relationship, there will be problems and fights. In the past, I loved to create problems which made it frustrating for my wife and I. But I thank God for giving me such a patient wife who never gave up on me. I can only repay her by being a better husband and father.
"When I was younger, I was immature and did not think of the consequences before I did something.
"Now that I'm married with three kids, I understand that there is no point getting into trouble because it affects my family and not just me any more."
After seeing Shakir play nine out of 10 national team games this year - scoring one goal and contributing to three clean sheets - former national coach Fandi Ahmad is convinced Shakir will do well for Kedah.
"He is a very reliable wing-back who can play in more than one position. He is good in defence and provides an attacking option with his overlapping runs," said Fandi.
"He will surely be an asset to his new team with his tremendous fitness, speed and aggression."
Kedah coach Aidil Sharin, who was also Shakir's mentor at Home United both last season and 14 years ago at the club's centre of excellence, added: "He is Singapore's best footballer this year. His work rate and defensive stability are rare qualities in this region.
"Some coaches may have had a hard time with him, but he has been superb with me and, hopefully, we will be successful together again."
Even as those around him attest to his positive transformation, there is something Shakir will not change - the ferocity of his game that caught the eye of coach Diego Simeone after he snapped at Radamel Falcao's heels and dispossessed Diego Costa when Atletico Madrid visited Singapore in 2013.
The 1.79m, 65kg defender said: "I am not the biggest left-back around, so I have to rely on my speed and I have to be clever in how I defend against them.
"If I have to impose myself against a bigger striker, I will not hesitate to do so, otherwise they will know they can take advantage of you.
"I'm grateful to sign with Kedah. My longer-term aim is a better contract, or move on to play for a better team from a better league because I won't be satisfied to remain on the same level."