The free-agent center is expected to explore other options in July, but he could re-sign with the Lakers for up to $118 million.
"I really have always had a very positive relationship with him ever since the 2009 playoffs," said Jackson at a Time Warner Cable media event last week. "You get really close to players when you get in a final series. You not only go against them, but you also [gain] great respect for them."
The Lakers defeated Howard and the Orlando Magic to win the 2009 title — with Jackson on the bench.
"Dwight wants to get back to that place and I admire that about him," Jackson said. "The work that he has to do to get there is going to be continual."
Outside of his relationship with fiancée and Lakers executive-owner Jeanie Buss, Jackson doesn't have any true influence on the team's basketball decisions.
Jackson said he sent a couple of texts to Howard last year, giving him support after back surgery. As a New York Knick, Jackson sat an entire year with a similar injury.
"I told him to remember defense and rebounding are the keys to the game," Jackson said. "He texted back to say, 'Is this really you?'"
Howard hasn't revealed his preference publicly, and momentum suggests he might leave for the Houston Rockets — but the decision won't truly be made until July.
In May, Jackson questioned Howard's reason to return to play for Coach Mike D'Antoni.
"Would you? If you felt like your game wasn't going to be featured?" said Jackson on "The Dan Patrick Show."
Jackson will make his second appearance on Time Warner Cable SportsNet's "Through the Lens" on Tuesday night, reminiscing with longtime Lakers photographer Andrew Bernstein.