PORTLAND, Maine -- With the sun setting and the temperatures dropping last Thursday evening, a bundled up Billy McMillon hopped out of the dugout and jogged to home plate as the public address announcer called his name and the half-filled crowd at Hadlock Field stomped their collective feet. It was Opening Day for Double-A Portland, and for the first time in 19 years, McMillon suited up as a Sea Dog.
The first time McMillon donned the Portland jersey was way back in 1995 -- when Bill Clinton was in the middle of his first term, America Online was gearing up to offer World Wide Web access to the general public, and many of this year's high school draft picks to-be were born. McMillon was a 23-year-old outfielder making his way up the Florida Marlins farm system.
Two decades later, McMillon is now the first-year manager of the Sea Dogs. He spent the last two seasons with High A Salem, the two before that with Low A Greenville. After he guided Salem to the Carolina League championship to cap off 2013, the Red Sox bumped him up to Portland.
Just like his players, McMillon is trying to climb the ladder to the major leagues. It isn't quite the same the second time around.
"It's way different," said the 42-year-old McMillon, who played parts of six major league seasons with the Marlins, Phillies, Tigers, and Athletics and retired after the 2004 season. "There are 12 position players on the team. There's one manager. I think you have to be a little more lucky and fortunate on the side that I'm on now. I think it's a lot easier to get there as a player than as a coach or manager."
McMillon doesn't remember a ton from his first stay in Portland. It was one of his five minor league stops in five years, and although the difficulty of Eastern League travel is starting to come back to him -- an eight-hour bus trip from Trenton to Maine that got the Sea Dogs home at 7 a.m. last week helped with that -- McMillon can't readily recall too many specifics.
Part of that, McMillon acknowledged, is maturity. He was a kid by comparison at the time, and he didn't completely appreciate a life in baseball. That 1995 Sea Dogs squad had a number of future major leaguers on it, including catcher Mike Redmond and an 18-year-old Edgar Renteria, but it wasn't until the end of McMillon's playing days that he started to keep mementos -- some physical, some mental -- to remember the good ol' days.
"It didn't dawn on me that some of the friendships that I had, some of the games might've been special enough to put some special emphasis on," McMillon said.
That's different now. When Salem won the title last September, McMillon kept a bat signed by the team and a photo of the celebration. When top pitching prospect Henry Owens threw a six-inning no-hitter Opening Day -- McMillon's 300th managerial win, he was told -- he kept one of the balls Owens threw.
McMillon's mission is the same as it was two decades ago -- ascend to the majors -- but the measures by which one earns a promotion couldn't be more different. The standards are far more intangible for a managerial or coaching prospect.
Further complicating McMillon's goal is the increasingly less linear path to a major league bench. In his coaching career, Redmond, for example, jumped straight to the Marlins bench to manage from leading a High A team, while Robin Ventura (White Sox) and Mike Matheny (Cardinals) are two examples of former players getting major league managing gigs straight out of retirement.
For McMillon and others who have followed a more deliberate path -- like Arnie Beyeler, Torey Lovullo, and Kevin Boles in the Sox organization -- it can be frustrating.
"I don't know what the formula is," McMillon said. "I just know that as I go about my job responsibilities here I just have to make sure I do the best I can. Hopefully somebody takes a liking to me, or notices me, or I prove to them that I can be an asset."
When an organization is considering moving a player prospect up a level, it looks for certain indications he is ready -- maybe a consistent plate approach, for example, or improved footwork defensively. When it comes to evaluating coaches, it's not as clear-cut.
"There's some nuance that goes into coaching and managing at different levels," said Red Sox director of player development Ben Crockett. "Certainly in this case Billy proved his ability to handle the lower levels and did a good job in Salem last year with a nice mix of younger and older players."
Some of those players joined McMillon in making the jump from Salem to Portland. Owens, catcher Blake Swihart, and second baseman Mookie Betts were all, at times, part of Salem's success in 2013 and are now playing for McMillon again in Portland.
That mirrors the transition for Kevin Boles, who is with Triple-A Pawtucket this year after managing Portland in 2013. Third baseman Garin Cecchini, righty Anthony Ranaudo, and catcher Christian Vazquez are among those Boles is guiding for the second year in a row.
The organization sees some value in that from a player-development standpoint.
"It gives the ultimate consistency in terms of teaching from one year to the next, which is certainly a positive," Crockett said. "When that doesn't happen, you get a new, fresh perspective, build new relationships, things like that. But I think on the whole it's definitely a positive, and obviously Billy had a lot of success with a number of players on this roster."
Added Swihart: "We know what he wants, what he expects every day, so it's easier to go out and have fun and play."
Tim Healey is a feature writer for SoxProspects.com. Follow him on Twitter @timbhealey.