So when Reggie talks -- and he does a lot of that these days -- the Yankees listen.
He's almost always behind the batting cage before games, shooting the breeze with manager Joe Torre and general manager Brian Cashman, and he's been known to sit down next to Alex Rodriguez's locker and talk hitting with A-Rod.
This isn't a constant thing, though. Reggie picks his spots, bouncing around Yankee Stadium from time to time through the regular season and making the occasional road trip.
But now it's October, and, well, you know his nickname. Reggie says he feels now is the time for him to be available for anyone who wants to talk playoff baseball.
"I'm always a moving target," Jackson says. "I'm here for support, to answer questions and be here for them -- get them focused properly.
"I can read the club pretty good. I can talk to a player. My job is a little easier because I can see through the storms. I can tell them a lot of the time what's coming."
Torre says it's a positive influence, especially during the postseason.
"Reggie, at this time of year, this is his month," Torre said. "And Reggie is there for guys to sort of pick his brain a little bit, because the big part about playing this time of year, especially the guys who haven't played very much in October -- and I was one of them -- is to get a feeling of the game.
"For the great ones like Reggie, the game sort of slows down a bit. When you're not as experienced, everything seems to go a bit faster."
Jackson cited rookie second baseman Robinson Cano as an example of someone who has benefited from Mr. October's advice.
"I just told him that things might look tough, but he'd turn it around," Jackson says. "He might not have believed me when I said it, but look at him now."
Cano's three-run double ended up being the key hit in the Yankees' 4-2 victory over the Angels in Game 1 of the American League Division Series, and he added an RBI double to give the Yankees an early lead in Game 2.
One thing Reggie has to temper is talk of his own past accomplishments. Torre admits that Jackson's otherworldly playoff feats can intimidate players who haven't seen much October baseball.
"His expertise ... unfortunately, everybody doesn't have the ability Reggie had," Torre adds. "So when Reggie starts talking in terms of 'hit this one this far' or 'that far,' not a lot of people can relate to that. I don't care if you're veteran status or just a rookie.
"But Reggie is fun to have around because of his enthusiasm for the game."
That enthusiasm stretches beyond the Yankees or the Bronx. Jackson says that every time he returns to Angel Stadium -- he played for the Angels from 1982-1986 -- is special. While with the Angels, Jackson hit his 500th career homer on Sept. 17, 1984.
"The Angels hold a special place in my life," Jackson says. "The guy who checks my ID when I come in the park was here when I was here, so it's always been a good place for me."
Still, it's a no-brainer who Jackson's rooting for in this series. He unabashedly predicts a Yankees victory, mostly based on the fact that their offense is full of sluggers and the team came into this series hot.
"I know our guys are a handful," Jackson says. "It's like being in a 31 Flavors and asking for a double scoop, then the guy goes and brings you a gallon.
"There are really good leaders here, and they're playing at a very high level."