Hennigan said that process took its next step via another tough decision he made in the final minutes of the Thursday's trade deadline.
The Magic traded veteran shooting guard and fan favourite J.J. Redick, along with centre Gustavo Ayon and reserve point guard Ish Smith to the Milwaukee Bucks in exchange for guards Doron Lamb and Beno Udrih, as well as forward Tobias Harris.
In a separate trade, Orlando also acquired forward Hakim Warrick and cash considerations from the Charlotte Bobcats in exchange for forward Josh McRoberts. The team said it intends to waive Warrick.
"As we evaluated all our options leading up to the deadline...We made the deliberate decision to go ahead and make this move because we feel like it sets us in a direction that we're trying to go, which is to create something that is sustainable," Hennigan said. "At the end of the day we liked the Milwaukee deal because we felt we were able to get back some players that addressed some needs for us. We got some players we feel fit the timeline we're trying to put together to create a competitive window."
Hennigan said the Magic talked to about a dozen teams about various trades. He said the decision to take Milwaukee's deal was made about four minutes before the deadline because the consensus was the pieces they picked up helped them long-term.
He acknowledged Orlando was also setting itself up for the future and he is looking to make his roster younger and build through future drafts.
Hennigan said he does that by acquiring two young players in the rookie Lamb, and second-year Harris. The Magic also pick up a true backup point guard in Udrih to play behind veteran Jameer Nelson.
The new players are expected to get physicals on Friday and could be ready to suit up as early as Saturday when Orlando hosts Cleveland.
But Hennigan's first call Thursday was to the departing Redick, who had said handled the news as a "professional" and was "a class act." But he dismissed the notion that the move was at all inevitable because of the possible asking price for Redick as he enters free agency this summer.
A former first-round pick in his seventh season, Redick was a coveted name on the trade market. A 2006 Orlando draft selection, he is averaging career highs in points (15.1) and field goal percentage (45.0).
Now in the final year of a three-year $19 million contract and is likely to seek a long-term deal this summer. By comparison Ayon, who was acquired this summer in a sign-and-trade deal, is making about $1.5 in his second season. Smith was a preseason free-agent signing and is making less than $1 million.
"It was not an easy decision for us by any means," Hennigan said. "It was a hard decision, and I'll be honest with you guys. But when you look at it, you take all the different parts and you analyze what was available, we felt like this was a move we had to do to further the process of trying to create competitive team that's gonna be competitive for a long time."
Redick said this week that he was pleased with Hennigan's candidness throughout the season and remained open to the idea of staying in Orlando to finish the season.
He also told reporters after the Magic's loss to Dallas on Wednesday night that he recognized he could also be dealt.
"I can sit here and say I don't want to come back, I can sit here and say I do want to come back. Ultimately, it's their decision," Redick said.
Redick was a restricted free agent when he signed an offer sheet with Chicago in the summer of 2010, but Orlando matched his deal. With no restrictions after this season, the Magic had no guarantee that he would re-sign.
Still, the decision to deal Redick was not an unexpected move for a Magic team that has parted ways with a franchise player in Howard and last season's NBA Most Improved Player in Ryan Anderson.
Having been a part of all three decisions, the 30-year-old Hennigan joked that "I started dying my hair two months ago." He said knows fans will begin looking for results from the moves sooner than later.
"What I can tell you is this is a pressure business," he said. "It is what it is. We feel that pressure. We embrace that pressure. It's something that you really have to look at from, I think, a bigger picture and bigger perspective and understand that there are decisions you make because you believe in the process.
"And we believe in what we're doing. We believe in the way we make decisions. We believe in the research we do. It's our hope that our fans believe in that with us."
Follow Kyle Hightower on Twitter at http://www.twitter.com/khightower.Suggest a correction