But his form soared following that decision and it was reported he was reconsidering in the weeks following, which culminated with a complete change of heart on a post-season holiday.
"I had a number of really positive chats with Hirdy (James Hird) and Paul Little, and the boys were constantly in my ear, encouraging me to change my mind," Winderlich said.
"Our recent family holiday gave me time to weigh everything up, and I felt I still had a real hunger and the ability to go around for another season.
"To have Mark Harvey return as an assistant coach is exciting for me personally, and it's a massive boost for the playing group and the footy club in general."
Winderlich also said regular sessions with a chiropractor made him confident his body could stand up to another season.
"My body is feeling the best it has in a long time. The sessions freshened me up and allowed me to play some really consistent footy last season," he said.
"While there's no guarantee, I'm confident in my body and excited about what this season has to offer."
Coach James Hird said the 128-game player would continue to bring leadership and versatility to the team in 2015.
"Jason is a very popular member of the playing group, and we all love having him around the club," Hird said.
"He adds a particular element of class to our forward line, but he is also impressively versatile.
"Jason's history with injuries has been well documented but his body held up well this year.
"He played one of his best seasons to date so we're thrilled that he's reversed his decision to retire because we know he still has plenty to offer."
GETTABLE: Giants up ante for FA, Dons trio's deals, North gun's future 'unclear'
Riley Beveridge and Cal Twomey are joined by Mac's Sports Tom McConville, discuss the 'Trading Revolution' and a special treat in honour of Harley-mania
02:15
Match Previews R7: Richmond v Melbourne
Sportsbet's Nathan Brown and Kane Cornes preview the game between the Tigers and the Demons at the MCG
01:23
Michael Barlow Medal: The best R6 cash cows
Roy, Calvin and Warnie deliver the round six Michael Barlow Medal votes
06:45
The Traders' Fantasy preview: round seven
Calvin, Roy and Warnie talk you through all the news, captains and more