Not surprisingly, it was at the same time when Wisconsin got the resume-building wins it so desperately needed after letting them slip by in the nonconference season.
Opening the conference play with only six combined points in nail biting wins over two of the conference's sub-par teams, Jackson needed to pilot Wisconsin past No.15 Illinois and then go on the road to No.2 Indiana, two teams that would test any young point guard physically and mentally.
"That was an important stretch to our season," said associate head coach Greg Gard. "He approached it like any other games. His play helped us get moving in the right direction."
After back-to-back double-digit efforts in wins over Illinois and Indiana, Jackson started to see the slower pace, allowing him to facilitate the offense, distribute the ball and make plays within the offense. In short, he became the point guard UW needed him to be.
"I had more starts under my belt and got that full confidence," said Jackson. "I knew I could play. I've always expected that. It felt really good when you start to see things before they happen."
Jackson started off the season with the basketball world buzzing by him in a blur. After playing in only 17 of 36 games a season ago, he was suddenly thrust into a position to be a big-time contributor at the point guard position vacated by the injury to Josh Gasser.
But when Jackson tried to play like an All-American in preseason practices, he faltered and caused the Wisconsin coaching staff to go with redshirt freshman George Marshall for the first six games of the season.
"I think his personality, swagger and air about him has helped him through times when the goings been rough and he's had to improve," said Gard. "It hasn't always been smooth sailing, but that confidence has carried him through and not allowed him to get down on himself. He's had a lot to learn, he's grown a lot. He's not there yet, but he's definitely taken steps in the right direction.
"The belief in himself has been a huge aid in getting him through this."
There's no question Jackson has evolved for No.22 Wisconsin (21-10) – who faces No.6 Michigan (26-6) in the Big Ten Quarterfinals Friday afternoon here at the United Center – but the question is what area has Jackson improved the most.
Naturally a two guard but having rotated at the point guard role at Westerville (OH) South High, Jackson went from averaging only 5.4 minutes and 1.1 points last season to 27.1 minutes and 6.5 points in 31 games entering the postseason. He also was better with his ball handling, having 14 assists to only four turnovers on a three game stretch in late February.
Defensively Jackson leads the team with 32 steals and routinely takes the challenge of guarding the other team's top offensive guard.
"They have a really good team and it starts with Tray," said Michigan sophomore guard and conference player of the year Trey Burke, a former AAU teammate of Jackson's. "I work out with Tray in the summer and we're in the gym pretty much every day together."
It's evident that some of Burke's shot making has rubbed off on Jackson, and bubbled to the surface at the most opportune moments.
- In UW's 45-44 win over No. 12 Minnesota, Jackson scored the Badgers' final four points of the game on a pair of jumpers in the closing minutes, including the game-winner with 2.1 seconds left.
- During UW's double-overtime win over Iowa, Jackson hit a game-tying 3-pointer with 29 seconds left to send the game to overtime.
- In the regular-season finale at Penn State, Jackson buried a 25-foot 3-pointer as time expired to give Wisconsin the 63-60 win. He led the team with a career-high 15 points.
"We grinded it out and luckily we got the victory," said Jackson. "I think that any one of the guys on our team could have hit that shot because we all have that confidence. When you are in that position, you just have to step up. Hopefully more times than not it falls and it did on Sunday."
Jackson has also shown confidence in his abilities when he's been challenged. Two games after his big shot helped beat Iowa, Jackson had a chance to beat Minnesota on the road, but mismanaged the final 30 seconds that would have won the game in regulation. He tried to make up for it in overtime, but is 3-for-14 shooting performance and three turnovers spelt doom for UW.
He responded the next game with 10 points against Ohio State – his father's Alma Mater.
"It's been an ongoing process, even in practice," said Gard. "There are things in practice he hasn't done well and there are things in games he hasn't done well, so it's been a consistent, constant building of good habits of what you can or can't do. You are only as good as your last one."
The major adjustment for Jackson has been playing with big men. At Westerville, Jackson said he was the second tallest player on his team his senior year. Of the 13 players on Wisconsin's active roster, Jackson is the fourth shortest.
"I like to call them footers, guys setting screens and playing pick-and-rolls," said Jackson, who leads the team with 86 assists. "It's exciting playing with bigs. You have to bring everything you got. It's a totally different game when you have footers out there."
Jackson knows he will need to rely on Wisconsin's three footers – Mike Bruesewitz, Jared Berggren and Ryan Evans – if the Badgers want to win their first tournament championship since 2008. Of the 15 combined Big Ten Tournament games on UW's roster, the three senior forwards have 11 of those games, including all six starts. They also account for 62 of UW's 67 Big Ten Tournament points on the active roster.
It'll be Jackson first Big Ten Tournament game, and his responsibility once again is to find the footers and have some fun doing it.
"It's about going out there and just playing and being aggressive," said Jackson, referring to Wisconsin's 79-71 win. I remember specifically from last year against Indiana, that's what we did. Everybody came out and played loose and had fun. That's when we are at our best this year."