Well, he did it. In his final final as Linfield manager David Jeffrey came out on top.
Was there ever any doubt? Quite a bit actually when the County Antrim Shield decider on Tuesday night ended up going to a nerve-jangling penalty shoot-out
It wasn't just Linfield goalkeeper Jonny Tuffey who was key to the drama that saw the Blues overcome Crusaders at the Ballymena Showgrounds. I fancy fate played a hand too.
The first trophy Jeffrey won as a young player at Linfield was the County Antrim Shield courtesy of a 4-1 victory.
And here he was, in his last season as Blues manager, more than 30 years later winning the County Antrim Shield again... 4-1 on spot-kicks after a scoreless draw.
As Jeffrey lifted the giant trophy towards the delirious Linfield supporters he felt a huge surge of pride.
No doubt in a quieter moment at the end of another successful evening, Jeffrey would have reflected on that determined kid, with a big mop of blonde hair, all those years ago collecting his first medal.
I hope on Tuesday he afforded himself a smile thinking just how far he had come as a man, manager and Windsor Park hero.
The victory over Crusaders took Jeffrey to 31 trophies as Linfield boss. Staggering.
He is now level with the great Roy Coyle in terms of silverware carried into the Windsor boardroom.
Between them these two men, with different personalities but that same insatiable appetite to succeed and debilitating fear of failure, have brought 62 trophies to one club.. so far.
When Linfield chose Coyle and Jeffrey, they chose well.
It makes you wonder why the Blues haven't tried everything they can to stop big Davy from leaving because it'll be virtually impossible to find anyone better.
We'll come to that shortly but first the fascinating Coyle v Jeffrey debate and which one deserves to be labelled the best Blues boss ever.
Jeffrey could win the league title with Linfield this season taking his tally to 32 and I guess kill the argument, but that's for then... let's live in the now where with 31 trophies they can't be split on the numbers.
Coyle was manager of the Blues from November 1975 to April 1990. In that time he won an incredible 10 league titles, three Irish Cups, seven Gold Cups, four Ulster Cups, five County Antrim Shields, one League Cup and one All-Ireland Cup. Jeffrey played in many of those triumphs.
Jeffrey became boss in January 1997 and since then has won an amazing nine league titles, seven Irish Cups, six League Cups, six County Antrim Shields, one Setanta Cup, one IFA Charity Shield and one Floodlit Cup.
Still hard to separate them. Delve a little deeper though and a victor can be found.
There is a theory that Coyle's teams played against tougher opposition, but remember in his day there were more trophies available to win.
It's also worth noting Roy won the Irish League and Irish Cup double three times, while David did it on six occasions in seven seasons and in the 2005-2006 campaign he guided his team to the Grand Slam, claiming every domestic trophy available to them.
Both built several successful sides and made many outstanding signings (there were some duds too) though Jeffrey snapping up Glenn Ferguson from Glenavon when Coyle, managing Glentoran, was chasing him was the pick of the bunch.
In terms of management styles, Coyle ruled with a rod of iron while Jeffrey, also capable of being ruthless, has preferred to adopt more of a velvet glove approach. Whatever their methods, they clearly worked.
As both will tell you the pressure of being Linfield boss is intense. It's to their credit that they lasted so long in such an unforgiving job.
At the end of the season Jeffrey will leave as the club's longest serving manager and in my book, whether he beats champions Cliftonville to the title or not, he will do so as Linfield's greatest manager ever.
As to who is the greatest Irish League boss of them all, that's a different debate. After leaving Linfield, Coyle won trophies at Ards and Derry City and brought honours galore to Glentoran which takes some beating.
If anyone could do it in the future though, Jeffrey could, should he manage elsewhere.
While Davy made the decision to quit Linfield, isn't it strange, for all his achievements, a feeling in the local game still exists that he's being forced out, with certain board members content to see him go?
They will miss him when's he gone.
They have 31 trophies to tell them that.