On Wednesday night, his journey begins.
Along with Marlins vice chairman Joel Mael, game presentation and events supervisor Luis Dones and a trio of players -- catcher Brett Hayes and outfielders Mike Stanton and Bryan Petersen -- Jackson will be on the road for the next two weeks, through Dec. 15, visiting troops in Japan, Guam and Hawaii.
This is the fourth such visit to the troops the Marlins organization has put together and the second of the year.
"Everyone has said that it's a life-changing experience -- once-in-a-lifetime opportunity," Jackson said. "If you're not someone who's served in the military or doesn't have a close relative, it really opens your eyes to the level of sacrifice that these troops are making on our behalf and to see their living conditions, to see the type of things they have to deal with mentally and emotionally, physically, the distance, the rigors of the work, the training."
The activities planned, in cooperation with Armed Forces Entertainment, run the gamut: meet-and-greets, an adult softball game, a tour of Pearl Harbor in Hawaii and another of Hiroshima in Japan. There'll be baseball clinics, even dance clinics.
Joining the players and front-office reps on the tour will be team mascot Billy the Marlin, as well as Mermaids dance-squad members Ashley, Jackie and Stephanie.
"It's definitely an honor and a huge opportunity to go out and visit those who are risking their lives for us," Hayes said.
The locales the Marlins will be visiting this time are exotic, to be sure, but this two-week excursion would be wrongly labeled a vacation. In fact, if there were ever a time for a team to pass on a charitable opportunity, to keep its personnel and resources solely dedicated to the day-to-day tasks, it would be now in Miami. What the Marlins are going through this offseason isn't tantamount to, say, indoctrinating a new general manager -- the move into a new ballpark brings a seismic change in the off-the-field operations.
There's never been a busier six-to-nine-month period in Jackson's eight years with the organization, he said. But starting Wednesday, when he flies up to New York before heading out of the country, his focus and the focus of all the others he's traveling with will shift.
The organization knows it's worth it.
"My biggest concern was just time away from the office, particularly with the holidays kind of around it," Jackson said. "I don't like being out of the office that much. ... [The trip will] really just open your eyes and change your perspective on how easy we have it and how appreciative we should be of their sacrifice."
The Marlins made history in 2010, when they became the first Major League Baseball team to take active players to visit those serving in the United States military, visiting Iraq and Kuwait. Now, the trips are becoming tradition.
"We've tried to do some unique things and not just do the same old, same old," Jackson said. "We believe it's about more than just putting on some baseball games."