Healy admits that a run of four defeats at the start of his Blues tenure left him with sleepless nights but Northern Ireland's record goalscorer revels in bringing silverware to his boyhood club and acknowledges that taking the job meant going from hero to zero with some local fans
When Linfield won the Irish Premiership in 2017, it was their first League title in five years - that's an eternity at Windsor Park.
David Healy broke the barren spell. As manager, he's won another couple of titles since, the Irish Cup, League Cup, County Antrim Shield and inspired the team to unexpected heroics in Europe.
All this having come into domestic football in Northern Ireland amid a blaze of publicity with people doubting him before the ink was dry on his contract. 'He doesn't know the League, he's too inexperienced, the job at Linfield will destroy him,' they said. Another was, 'He's too nice'. The country's record goalscorer still smiles at that one.
Healy has proved them all wrong. He has been a monumental success at Linfield and his team have a shot at winning a fourth title in five seasons.
As driven as he was clinical at international level, that was outlined when the 41-year-old took the job in October 2015, replacing Warren Feeney.
Healy was a national treasure, loved by all. Having grown up supporting Linfield, he was well aware that by becoming boss at Windsor the hate would come. Instantly for some rival fans, it was hero to zero stuff.
Healy spoke to his family as well as trusted friends and former Linfield boss David Jeffrey. A few warned him about what was ahead but the Killyleagh native, always his own man, dived into the choppy blue waters planning to swim not sink.
He tells Sunday Life Sport: "When Warren left Linfield, quite suddenly I was contacted, met a few people at Linfield and was quite quickly offered the job. I hadn't done that much coaching, had certainly never managed and from going to games knew how demanding the supporters were but I also knew Linfield were a huge club and the challenge appealed to me."
Giving an insight into difficult early days and sleepless nights, Healy reveals: "I was probably nowhere near ready for what was in store in the days and weeks that followed but it was an incredible grounding for me.
"We started well but then went on a tough run in November, losing four matches. That was a testing time. I didn't sleep more than two hours per night the whole of that November worrying about us losing four games on the spin. There were questions in-house at Linfield and from gleeful people outside who can't stand Linfield.
"I had to prove I was the right person for the job. I had to regather myself and have steeliness in my mind to turn things around. As a player, I tried to prove doubters wrong and as a manager, then and now, I like doing that. I also like to prove the good people at Linfield right that they were correct in appointing me."
On the abuse that has come his way while in charge of Linfield, Healy says: "There have been occasions when rival fans have overstepped the mark but I fully understand we are the biggest team in the Irish League, I am the Linfield manager and there are people out there who don't like our club.
"I know there are Irish League supporters who are big Northern Ireland fans and cheered me on as a player who don't want me to do well now but all I can say to that is I am manager of Linfield and I will try my best for the club, our fans and our players.
"It hasn't surprised me the feelings rival fans have towards Linfield but what has surprised me a little is the effort teams put in against us in comparison to other sides. I've seen it, even at Under-12 level."
Remembering the Sir Alex Ferguson way at Manchester United, where he started his career, Healy makes a point of knowing the names of the youngsters coming through the youth ranks at Linfield. Insiders will tell you his work ethic and desire to assist all at the club, and not just focus on the first team, is extraordinary. He has strong relationships with captain Jamie Mulgrew and the rest of the players and staff and sees assistant Ross Oliver as an instrumental figure in what has been achieved so far with the Blues.
Ask Healy if he feels he's been successful at Linfield in his time as manager and he'll tell you the club has and that's what matters.
Before Covid-19 struck, there were eyes on the former Rangers, Leeds and Fulham striker from England and Scotland watching his progress as boss. No doubt those will come around again. With Healy's current Linfield deal up at the end of next season, the Blues would be wise to tie down the Windsor Park legend on a longer contract for when a cross-channel call eventually arrives.
Asked about his future, Healy says: "I want to manage at whatever level I feel my managerial and coaching capabilities can take me to. Any manager wants to go as high as they can. It's all about getting the break and it could be a couple of years down the line or five years down the line.
"Linfield have been good to me and I feel I have been open and honest with Linfield. I have always seen any of my contracts out. I have the rest of the season and another year left on my current deal and the club may want to discuss how we want to go forward.
"When I signed my first deal at Linfield, I was asked if I was only going to be here for one season and use the club as a stepping stone. To give the amount of work, time and effort to Linfield, I don't think I could be accused of using the club as a stepping stone.
"There are times at Linfield where I probably don't win everyone's affection and I include a small minority of fans in that but I love managing Linfield Football Club and the challenge of it. I also love winning trophies, helping the team and our players to improve and I want to continue to do that for as long as I am at Linfield."
Q: How do you feel about Linfield going full-time?
A: I'm excited. Credit to other Irish League clubs who have gone down this road already. Linfield have to make sure we aren't falling behind anyone on or off the pitch. We have been hugely successful here but we want to keep moving forward. Roy McGivern (Chairman) and Pat Fenlon (General Manager) and people at the top of the club have been pushing this and have come up with a plan and me as the manager, I want to oversee it. We may lose one or two players who may not be able to commit to full-time football but as a club we feel now is the right time to make the move to keep us where the supporters demand us to be and where the players and staff want to be.
Q: Last year you told me losing to Queen's in the Irish Cup was your toughest moment in football. Do you still think about it?
A: Absolutely. Through adversity and disappointment, you learn more about the people around you and I learned a lot that day. To give our players credit, following that defeat we were big and strong in our next game, winning at Cliftonville when a lot of questions were being asked about myself and the team. Our resilience and that victory catapulted us to another League title.
Q: On Tuesday, Linfield play Glentoran. The Big Two rivalry is finally as intense as it was when David Jeffrey and Roy Coyle were the managers. What do you think of Glentoran?
A: I have huge respect for the history and traditions of Glentoran as a football club and right now they are one of the talking points of the Irish League in terms of what's happening at the club and who is involved. Before he was recognisable in the League, I met Mick McDermott briefly when he came to watch one of our training sessions at Midgley Park. After that, steps were taken and Mick became manager of Glentoran. They have made giant strides under Mick and Windy (Paul Millar) and with all the investment at The Oval, I'm sure they will continue to provide a challenge for everyone. As manager of Linfield, I enjoy beating Glentoran more than anyone else. I'm sure anyone from Glentoran would say the same in relation to us.
Q: How can the Irish League improve?
A: In the five and a half years that I have been Linfield manager, I think the standard of play and coaching across the League has improved. I also think that the competitiveness of the League is an important trait and sometimes games here can be more value for money than Premier League matches in England but the majority of facilities and pitches at grounds have to and should be better. That would enhance the game here and be much better for supporters and players.
Q: It's 21 years this week since you first scored for Northern Ireland, aged 20, netting twice in a 3-1 win in Luxembourg. At that stage, could you have imagined you would hit 36 goals at international level and become the nation's greatest goalscorer?
A: I had belief in my ability but I wasn't thinking about breaking records then. I was actually behind others in the Under-21s pecking order but when Sammy McIlroy became senior manager, that turned out to be good for me. He had watched Manchester United reserve games I had been involved in, named me in his first squad and I'm forever thankful to him for that opportunity against Luxembourg.
Q: In the 2000s with all your goals, including famous winners against England and Spain, you were Northern Ireland's biggest sporting hero. How do you feel looking back on that?
A: Privileged and honoured to represent my country. All I wanted to do was help Northern Ireland. We had some great results in that period but we also had some bad ones. The defeats were hard to take but the most frustrating thing for me back then was the players who I felt let the country and our managers down, refusing to play or refusing to travel and making up excuses to get out of international duty. It annoyed me then and I still can't understand it now. Whether I had been scoring all those goals or not, I would have done anything to play for Northern Ireland.
Q: Does a week ever go by in your life when that goal against England in 2005 isn't mentioned to you?
A: Yes, people still talk about it. I have bumped into so many fans over the last 16 years who say, 'I was there'. I reckon we must have had 25,000 supporters inside Windsor when we beat England! I'm happy it brings back magical memories. It was a great night.
Q: Northern Ireland reached the Euro 2016 Finals after you retired. Was there a part of you that felt you should have been there playing in a major tournament after everything you had done in a green shirt?
A: Not at all. Would I have loved to have played in a major Finals at some stage for Northern Ireland? 100%, but I don't feel sad I wasn't at Euro 2016. I was delighted for Michael O'Neill and the players to go to the Euros and come home as national heroes. Our country doing well means more to me than personal glory and not just in football. I want to see our sports stars like Rory McIlroy, Carl Frampton and Jonathan Rea succeed and I want to see Northern Ireland flourish in fields outside of sport too.
Q: Who were the best players you played with at international level?
A: Steven Davis, an incredible talent, Keith Gillespie, who set up many of my goals, and Jonny Evans, a high-quality defender. It's great to see Steven and Jonny still playing so well at Rangers and Leicester.
Q: Which player you played against at international level made you go, 'Wow'?
A: Andrea Pirlo. We played against Italy and before the game they strolled out as if they had just come off the Milan catwalk. They looked immaculate in their Armani suits and sunglasses and Pirlo was so cool. When the game started, none of us got anywhere near him. He was unplayable.
Q: Is your biggest dream to manage Northern Ireland?
A: I would be lying if I said I didn't want to manage Northern Ireland at some stage. In my opinion, the ultimate in management is to manage your country but I understand that if it ever happens it would be a long way down the track. I could say I want to manage Northern Ireland in 10 or 15 years but by then I might be unemployed and not have a job in football. Look at people like our own Iain Dowie and Steve Lomas who had success as managers a while back but aren't working now. Of course it's a dream to be in charge of Northern Ireland in the future but in football management there are no guarantees.