He knew some in the Saints hierarchy had been angry with him after he had run a poor two-kilometre time trial at the start of pre-season.
He understood his sub-par performance that day had shaken the football department's confidence in him.
That the effort came on top of an injury-interrupted 2012 didn't help although, according to Winmar, he'd ended with an improved showing in the final month of VFL football.
The Saints say they had several chats with Winmar during 2012, including the post-season review, to communicate their concerns with his form and fitness.
After the disappointing time trial, head of football Chris Pelchen said the club counselled Winmar again.
"We explained that we would provide every possible chance for him to reach the necessary standards," Pelchen said.
Winmar had a year left on a two-year contract and was, in his view, fitter than his original time trial had indicated.
So he soon thought he was back on track.
When the draft passed, any anxiety disappeared.
But one final deadline for delisting remained.
St Kilda told him soon after the draft that he was being delisted.
While Winmar knew what was being said, the words passed through him.
The Saints had made a hard-headed decision.
"AFL list submission 3 at the end of November is the final opportunity for clubs to make changes to its playing list ahead of the next season," Pelchen said.
"It was at that time we made the difficult decision of parting company with Nick, who was a respected member of the player group and who will always be welcome at the St Kilda Football Club."
That left the 21-year-old, who played two games in three seasons (he played rounds nine and 10 in 2011) with few avenues to join another club. Only the rookie and pre-season drafts remained, unless a team wanted to recruit him as a delisted free agent.
While the club's actions were within the rules and Winmar's contract was settled, the AFL Players' Association thinks St Kilda exposed a major crack in the system and the rule should be changed.
They say the effect on a player that finds himself in Winmar's situation is too large.
And many in the football industry agree, knowing that a brutal culture needs to have boundaries that protect those who act in good faith.
The chances of another club selecting a cut player in a pre-season or rookie draft in that time frame are minimal.
Particularly when, as Winmar says himself, no matter what the circumstances, the perception that surrounds a player delisted at that time of the year is negative.
"It almost made me look like I was undesirable," Winmar told AFL.com.au.
What he was to the Saints, it appears, was less desirable than Fremantle's Dylan Roberton, who St Kilda signed a week later as a delisted free agent.
As the rules allowed the Saints to make the call when they did, they did.
The club says Winmar is always welcome so he is clearly, as many have said, a good kid.
The Saints have welcomed a review of the guidelines.
When the running defender's name was overlooked in both the pre-season and rookie drafts, it was no real surprise but it left Winmar in a bind as to how to spend 2013.
"It was almost too late for me to plan to do anything this year. I had no idea whether I was going to Uni [or] work even," Winmar said.
Despite his shock at the time, he admits the club was pretty good to him on the day but being a Perth boy in Melbourne he had few outside the club to turn to in the moment.
His girlfriend, Hannah, flew down from Sydney to help pick up the pieces and they returned to her place the next day.
Winmar spent some time there to clear his head and think about what his next step might be. He decided to return to Perth and play football for his original club, Claremont.
He is doing casual work and is resilient enough to say he's happy enough now that the dust has settled.
Despite not saying too many good-byes on the day he found out his days at St Kilda had ended he bears no hard feelings.
"I met some really nice people and good blokes. I wish the best for them," he said.
Now he is focusing on playing well for Claremont and, despite occasional reports to the contrary, he remains keen to resume an AFL career if another chance arises.
But he does think the rule is wrong and needs to be changed.
According to Winmar, players should get a chance after delisting to be picked up in the NAB AFL Draft and, just as importantly from the player's perspective, an unfair perception can be avoided.
"I definitely don't want this to happen to anyone else," Winmar said.