"Des has a contract for as long as he wants, really," Penn said at the time. "He is absolutely there next year.
"We will deal (with the years after that) in the off-season. But it's not an issue."
Fast forward two months and Hasler is gone.
Sacked by Penn and his board with a year to run on his contract after six weeks of ugly headlines and a situation at the club that had clearly become untenable.
On numbers alone, no person has played a bigger part in Manly's history than Hasler.
Across a combined total of 559 games on and off the field, a Manly club record, Hasler won two premierships as a playmaker and two as coach.
And while his exit following the 2011 title win was ugly, he and Penn appeared to have buried the hatchet when Hasler returned to the club in late 2018.
A rainbow-striped jersey, and the fallout from its creation, erased all that good will.
Hasler remains adamant he did not know of club plans to roll out the inclusion jersey, which had first been pitched to Manly in February.
Nor did several of his players, with seven opting to boycott the crucial July 28 loss to the Sydney Roosters on religious grounds.
Manly would not win again this year.
The Sea Eagles' seven-game losing streak led them to plummet from the top-eight to well out of finals contention by full time of their round 25 defeat.
Hasler's future was immediately placed under the spotlight, with the former playmaker only guaranteed an extension beyond 2023 if Manly finished in the top six.
The coach, too, had seemingly caused ructions in the week of the jersey saga.
With Manly between CEOs, and owner Penn still back home in the USA, the long-term coach appeared in front of the media alongside captain Daly Cherry-Evans at the height of the issue.
In an 11-minute apology, the coach conceded the club had made a grave error in not consulting players before unveiling the jersey and apologised to everyone from his own squad, to the NRL, the LGBTQI community and people living with a disability.
When asked by a reporter why it was him facing the media on such an issue, Hasler responded, "You'll have to talk to management about that".
Penn had promised a thorough review of the saga when he touched back down in Australia on the day of the Roosters game.
He was determined to find out how the club's planned message supporting 'everyone in league' had turned so divisive, and hoped to uncover why players and some staff had been kept in the dark.
So far, Hasler is the only high-profile casualty at Manly in an off-season headlined by talks of a fractured playing group and a long-term succession plan with Anthony Seibold the favoured new coach.
At the heart of it, too, has been a power struggle at the club, with new CEO Tony Mestrov desperate to find stability and Hasler renowned as something of a micromanager.
The long-serving former coach is known for having his fingerprints on everything at the clubs he works at, and Manly are desperate to turn over the page to a new era.
The situation has not sat well with some former players, who are adamant the jersey saga cannot be split from Thursday's decision to dispense with Hasler.
"It was because of the pride jersey," a furious Mark Carroll told SEN.
"Why was Dessie out there to be hung out to dry? He did that speech, which was probably his best-ever speech, but he shouldn't have been doing it.
"Why wasn't the CEO or why wasn't the boss of Manly doing that?
"I can't believe he's actually had to fall on his sword because he bleeds maroon-and-white. Dessie has done everything for that club."
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