Having enhanced his game to unseen levels, the 27-year-old seems destined to return to the bright lights of the big show - a bittersweet realisation for everyone at the North Shore club.
Speaking on the eve of the second game of the grand final series at Perth Arena (tipoff 11.30pm NZT), Jackson shrugged off any talk of his own swansong but he did appreciate the finality of the occasion for Boucher and, possibly, coach Andrej Lemanis.
"Everybody's talking about it but that, but [for me] we'll probably talk about it after the season," he said. "We definitely want to make history together, we definitely want to try to close out this series together - we're doing everything together because this might be the last time.
"But we haven't really thought about that, we're just worrying about Perth and their gameplans and everything that they'll probably throw at us tomorrow night. We've got our hands full with that."
Jackson is not wrong about that, with these Cats too tough for even Gareth Morgan to eradicate. The Breakers couldn't win game two on the road in the same situation last season but Jackson was pleased to again find Perth in the opposite corner.
"It matched up perfectly," he said. "Everyone wants to see No 1 vs No 2 going at it in the championship game. I wouldn't have it any other way.
"It's great we get the chance to play in a great venue - it's a really nice place to play and hopefully we can close it out and win here."
Jackson has seen his fair share of nice venues, having led Cleveland State to the NCAA tournament in college before playing for the Cavaliers, Spurs and Wizards inbrief NBA stints.
But as far as this part of the world goes, no venue provides the atmosphere of Perth Arena. With the vacant blue seats extending high into the rafters during yesterday's practice, the venue seemed set to provide the Breakers a typically friendly Western Australian welcome.
"We really don't worry about the crowd," Jackson said. "We play for this moment and we grow over the course of our careers to play with the loud noise."
Jackson admits that focus may have been lacking during the 15-point defeat to the Wildcats in the last game of the regular season - with the Breakers having clinched the minor premiership and choosing the occasion to honour Boucher - but he was adamant that was a one-off.
"There were a lot of things playing into that, but now we're not making any excuses for this time.
"We're looking forward to playing a tough team. We know they're going to be fighting for our lives so we're expecting it to be a tough 40 minutes."