For seemingly the first time in months, the humidity has finally calmed down. It’s late July, and the Myrtle Beach Pelicans are in Woodbridge, Virginia preparing for a doubleheader. A little breeze picks up at Pfitzner Stadium, an old metal hunk of a ballpark, making the flags dance in left-center field on this gorgeous late Sunday morning. Music plays softly on the speakers and the sun doesn’t leave a spot on the field untouched. Manager Buddy Bailey, keenly watching his players getting ready, smiles. “What a beautiful day,” he says. “It feels just like fall.”

A few hours later, the Pelicans lose both games to the Potomac Nationals. It’s onto the bus, this time a drive to Frederick, Maryland, about an hour and change north. How many of these has he ridden? How many miles of twisting back roads and sprawling highways has he looked out of the window to see? How much time has he been given to contemplate baseball, even life, just sitting in that front seat? The pages of the calendar never stops turning, years have bunched into decades and time is undefeated.

Buddy Bailey became the 11th manager in Minor League Baseball history to reach 2,000 wins. (Larry Kave/Myrtle Beach Pelicans)

What’s funny is, during games he never smiles. There are comments about it from fans and front office staff randomly throughout the year. Why does he never smile? How can his expression constantly be the same? But they don’t know him, the true him, and they don’t see what the players and coaches see.

The next day, Zack Short, an infielder from New York, is taking batting practice. He finishes his first round rather frustrated with himself. Bailey meets him at the side of the batting cage. Low line drives, Bailey says. Where do these towering fly balls get you?

Batting practice finishes and the players scurry to pick up stray baseballs. Short, walking off the field, is again met by Bailey. The two talk quietly near the third base dugout, and soon, everyone else is gone, climbing the stairs next to the stands to amble back into the clubhouse.

Buddy Bailey is in his 12th season in the Chicago Cubs’ organization and 29th as a manager in Minor League Baseball. (Larry Kave/Myrtle Beach Pelicans)

Suddenly, Bailey morphs into action. He may be a small-town Virginia boy, but his mind moves like a Manhattanite. Using his fungo bat as an example, he explains to Short a tiny, almost imperceptible, flaw with the infielder’s hands in the beginning of the swing. Bailey gives the bat to Short, and then carefully, delicately, maneuvers Short’s hands on the right path.

It’s an amazing sight to see. Fans have started to slowly trickle in, it’s not all that far from gametime, and here’s a manager so determined to make sure this miniscule split-second of his shortstop’s swing is perfect. Hit my hand, Bailey says, placing his left hand in the middle of an imaginary strike zone in front of Short. Watch your loading position. Okay, swing a little harder now. Do it again.

Countless practice swings later, the teaching session is finished. Bailey turns back to the dugout and, if only for an instant, the smile appears again. He doesn’t know it now, but in a few minutes, Short will use those lessons to record three hits that night, sparking the beginning of a 17-game on-base streak. And of the fans who went down to their seats early, most are either talking quietly to one another or staring at their phone. Almost nobody realizes that a chance to watch a legendary moment in an illustrious career just passed them by.

Buddy Bailey has managed in the Braves, Red Sox and Cubs’ organization, respectively. (Larry Kave/Myrtle Beach Pelicans)

Welby Sheldon “Buddy” Bailey figured he’d coach football or baseball in some capacity, but he thought it would be at the high school level. A native of Madison Heights, Va., Bailey earned All-American honors at nearby Lynchburg College and was drafted by the Atlanta Braves in the 16th round of the 1979 draft. At Spring Training in 1983, though he didn’t know it at the time, his life was changed forever.

The Braves were managed by Joe Torre, and apparently word had reached him that Bailey, a .210 career hitter in 119 career games at the minor league level, wasn’t going to impact Atlanta’s organization as a player.

“He said the organization needed someone who can manage in the rookie league, and some people in the front office that had seen me a couple years ago as a player in the minor leagues had recommended me to be the guy,” said Bailey. “I tried to talk Joe out of it like a dummy. I said ‘No, Joe I’m only 24 years-old I want to keep playing the game.’ He said ‘Well if you want to stay in the game for a long time, obviously this would be a better avenue for you because the organization is trying to tell you something.’”

Buddy Bailey originally played in the Atlanta Braves’ organization. (Larry Kave/Myrtle Beach Pelicans)

Bailey declined the offer and went out for his day’s activities as a player. However, when he came back inside the clubhouse, he found that all his belongings in his locker had disappeared.

“I thought maybe someone is playing a joke for a minute,” Bailey said. “I asked a clubhouse guy and the clubbie said, ‘Oh, you’re a coach now, you’re in the other locker room.’ So I walk over by the coaches and my locker is right beside them.”

Baseball has a funny way of bringing you exactly where you’re supposed to be.

Bailey smiles when telling that story. It’s a fond memory of the very beginnings of a career that’s transformed his life. He helped build up the Braves’ dynasty of 14 straight division titles. He moved from Atlanta’s organization to Boston’s, where he helped lay the groundwork for the Red Sox’s historic 2004 World Series championship. Then it was onto the Cubs, where he’s tutored nearly every young star who helped Chicago take their first World Series since 1908.

The Pelicans honor Buddy Bailey on August 24 after he won his 2,000th career game. (Larry Kave/Myrtle Beach Pelicans)

Buddy Bailey is one of 11 minor league managers to ever win 2,000 games. And he’s one of only seven people on the face of the planet to have earned two of the most desired championship rings in the history of sports: Those of the 2004 Boston Red Sox and 2016 Chicago Cubs.

It all had to start somewhere, and the Braves put Bailey in charge of the 1983 Pulaski Braves, a team in the Rookie-level Appalachian League.

At just 26 years old, Bailey drove to Pulaski, a tiny town of about 9,000 people tucked away in the hills of Virginia. It was there that Bailey was going to manage players ranging from 18 to 22 in age. One of the players was named Urban Meyer, who, like Bailey, would find great success later on in coaching, only on the football field.

“We only had nine position players for the first night we played,” said Bailey. “When I got there, we didn’t have a catcher, so I was leading the stretch, I was catching the bullpens and I was catching the live BP. I mean, I was still a player but still trying to get it all done to get it right.

“Then I said, ‘Well, I have to have a clubhouse meeting.’ So I’m sitting in my office and walk through the doors and then I got nervous a little bit. So then I walk in, and after about two words, I looked at the players and they hadn’t been in pro ball at all. They were whiter than this piece of paper right here. I said, ‘Guys, you’re sweating bullets and more scared than me.’ Then I was fine and that was that.”

Buddy Bailey talks to his team after winning his 2,000th career game. (Larry Kave/Myrtle Beach Pelicans)

In his very first clubhouse meeting, the specific point where everything can be traced back to in his coaching career, Bailey hit on something that people have been trying to peg for decades in his career. No matter what organization he’s managed in, no matter what generation of players he’s tutoring, no matter what area throughout the country and even the world he’s in, Bailey has been able to develop a unique connection and relationship with his team.

“He’s pretty good with communicating with us when we have the pregame meetings,” Pelicans third baseman Jesse Hodges said. “He tells jokes, he likes to laugh with us from time-to-time. He relates to you, but in his own way. It’s tough to explain but he knows how to do it.”

“He’s got a very unique personality,” said Chicago Cubs field coordinator Tim Cossins. “He’s got a very engaging personality, he’s a huge character and I think people that are around him for three minutes or longer understand how big of a character he is. When you get around him, I think people can connect with him.”

In Bailey’s very first year managing, he molded a squad of players he was barely older than and guided the 1983 Pulaski Braves into a 46–26 (.639) club. But now, with Myrtle Beach in 2017, that connection is much different to attain. At 60 years old, Bailey is more than double the ages of his players. But it’s sometimes those old stories from when he was first starting out as a manager that can bring everyone together.

Bailey managed in Pulaski again in 1984 before moving onto the Low-A Sumter Braves in 1985. The next year, he was elevated again, back into the High-A Carolina League with the 1986 Durham Bulls.

Bailey managed the 1986 Durham Bulls. (Photo courtesy of the Durham Bulls)

So much about Minor League Baseball has changed for players from when Bailey first began. Buses are much more comfortable, clubhouses are way more spacious, fields are better maintained and there are many more amenities in each of those three places they seem to spend much of their time.

So when the Pelicans’ players decided to pop in the movie Bull Durham on the bus ride from a road trip back to Myrtle Beach, Bailey stood up at the front to tell his team a tale from the past.

“He started talking to us about the movie Bull Durham because we were about to play it on the bus,” Pelicans reliever Jordan Minch said. “He just told us this whole story. He was the manager of that team, and he was sat down and interviewed a couple of times for the screenplay. And that just kind of blew all of our minds, just kind of like, ‘Wow, this guy really has done it all.’”

“He basically told us that the movie is about him,” said Hodges. “The guy that made the movie was asking him questions and picking his brain trying to see what it was all about. There are guys in the movie that he was coaching at the time, and I love that movie so to know that it’s about my manager is pretty cool.”

Bull Durham may have incorporated Bailey and some of his players from the 1986 Durham Bulls into the movie. And just by chance, two years later, with the film debuting in theaters, Bailey was back managing the 1988 Bulls.

Buddy Bailey skippered the 1988 Durham Bulls. (Photo courtesy of the Durham Bulls)

“We were going to play in Salem and they called and said, ‘Hey, we didn’t get to tarp down the field, the field is really messy, we’re probably not going to take BP if you guys want to come later, okay thanks,’” Bailey said. “So since it was check-out day in the minor leagues, everyone has to crowd in two or three rooms. I called around, ‘You guys want to go to the mall?’ ‘Sure.’ So we go to the mall at 12:15–12:30 and guys got themselves something to eat. Then we saw that Bull Durham was going to play at like 1:40. So as a team, all of us as the Durham Bulls walked into the movie theater in Salem, Virginia, and watched the movie as the Durham Bulls.”

It didn’t take long for Bailey’s reputation as a skipper to grow. Managing as high as Double-A Greenville in his nine seasons with the Braves, Bailey posted a 598–523 (.533) overall record. Prior to the 1991 season, the Boston Red Sox offered the Bailey an opportunity he could not pass up: the chance to come back and manage in Lynchburg, a mere two miles from where he grew up in Madison Heights.

“He was the first manager that I worked with in 1991, my first year in professional baseball,” said Lynchburg Hillcats general manager Ronnie Roberts. “I really didn’t know what to expect, but Buddy was extremely nice to me. I started off as a groundskeeper, and he explained a lot to me and told me what they needed to do on the field and when they needed to do it.

“I saw him coming out at 9 a.m. just to throw practice. Those were the days when we didn’t have a pitching coach or a hitting coach, so Buddy did a lot of stuff that managers don’t have to do these days. (He’s) just an extremely hard-worker, passionate about the game and teaching the game. He was as happy about a guy getting promoted than anyone.”

Buddy Bailey has had the opportunity to manage in his home area of Lynchburg, Virginia. (Larry Kave/Myrtle Beach Pelicans)

Bailey piloted the 1991 and 1992 Lynchburg Red Sox, oftentimes in front of his family and friends.

“When my father was alive, he would come to the games,” Bailey said. “And after the fifth or sixth inning, if we were winning, he would ride out the nine innings. If we were down even one run in the fifth or sixth, he’d go home. He didn’t want to see us lose.”

Bailey’s father stayed the full nine innings for Lynchburg games far more often than he went home. Bailey steered the Red Sox to a combined 144–130 (.526) combined record in his two seasons in the Hill City, earning a berth in the Mills Cup Championship Series in each campaign.

The two seasons in his hometown again impressed the front office Bailey was working for. The Red Sox tabbed Bailey to head Triple-A Pawtucket from 1993–96, and again from 2002–04. In between stints with the PawSox, Bailey was the bench coach for the 2000 Boston Red Sox, and also performed high-level duties such as advance scout, field coordinator and roving catching instructor.

Buddy Bailey managed Triple-A Pawtucket for seven seasons. (Photo courtesy of the Pawtucket Red Sox)

However, whenever he was still in the lines of battle, Bailey proved he could manage among the very best in all of Minor League Baseball. Almost as evidence, Bailey was named International League Manager of the Year in both 1996 and 2003, making him one of only four skippers in the circuit’s storied history to earn two yearly managerial awards.

“Genius. I think what most people don’t get to see, which we are all lucky to see, is during Spring Training, we have our daily reviews of our past days,” Cossins said. “When we have our game reviews, Buddy goes through it without a note sheet, without a paper, and he’s 100 percent accurate.

“We call him ‘Rainman’ in the meeting, and it’s just his recall. He will talk about games from 25 years ago as if they happened yesterday. That’s a special talent.”

“It seems like he studies the team that he’s going to play against two or three days before, in advance, and knowing which pitchers I’m going to have available to make a tough lineup,” said Buies Creek Astros manager Omar Lopez. “He’s going to make me think two or three times, which pitcher I’m going to bring up to face his hitters.”

Buddy Bailey shakes hands with Buies Creek manager Omar Lopez. (Larry Kave/Myrtle Beach Pelicans)

“He probably has more knowledge for the game than anyone I’ve ever been around,” Pelicans infielder Trent Giambrone said. “I feel like he’s very strong-suited for what he does, like he knows what’s going on before it even happens. And what’s pretty cool about that is that he helps prepare us for that.”

But even with all that success, baseball has a funny way of taking you back to where you belong. Bailey moved onto the Cubs organization and managed in Daytona (A+), Tennessee (AA), Iowa (AAA), and in both 2016 and 2017, Myrtle Beach. Back in the Carolina League for the fourth time, Bailey again has found his way back home to Lynchburg.

“When he comes here to manage, he has a whole cheering section,” said Roberts. “Sometimes when he is here managing the Pelicans, I feel like he has more people here cheering for the Pelicans than the Hillcats do on some nights. He’s very well-known, very well-liked and everybody who knows him likes him and they’re proud of what he’s done.”

“Baseball is baseball, it doesn’t matter where you’re at,” Bailey said. “You’re taking the team in to represent the Chicago Cubs, which we are with the Myrtle Beach Pelicans. And that, to me, is the №1 commitment I have being in Lynchburg, Salem, anywhere is no different.”

Buddy Bailey has won two minor league championships, six Venezuelan Winter League titles and the 2009 Caribbean Series. (Larry Kave/Myrtle Beach Pelicans)

Every so often when the Pelicans head up to Lynchburg, that faint smile will come out, if only just a brief second. But those who really know him, truly know him, know to ask him about Venezuela.

Bailey has been heading to Venezuela every winter since 2002. In America, many fans just see him simply as a minor league manager. He’s there during the games, but they’re more there to see the future of the game, not the past. But as the skipper of Tigres de Aragua of the Venezuelan Professional Baseball League, Bailey is something of a legend in the present. He’s steered the club to six league titles and the 2009 Caribbean Series title, in the process earning the 2006–07 Manager of the Year award.

“Inside the country, baseball is №1,” said Bailey. “There’s a real love and passion for the game of baseball, and I can’t describe it. People almost have to go see it for themselves and see how it is.

“Obviously, playing in the finals like that and getting to that level of emotion and responsibilities, it’s a real challenge and pumps your adrenaline. So anybody in life that really doesn’t love adrenaline rushes because of the responsibility or whatever the moment is, you’re probably not going to have much success. You’ve got to welcome it, and down there doing that, it’s a great thing and fulfills something inside of you that’s challenging every day.”

Buddy Bailey manages Tigres de Aragua in Venezuela. (Photo courtesy of Tigres de Aragua)

Similar to his first opportunity in the United States with the Braves organization in 1983, Bailey initially declined his first chance to manage in Venezuela. But while nobody in the country could move his locker down into South America, the next year, Tigres de Aragua gave him one more phone call.

“I thought I have to go or else they will shut the door and not give me another opportunity,” Bailey said. “So I’m going to go, and luckily I had a 19-year-old kid that was going be a superstar, Miguel Cabrera.”

Helped by the presence of Cabrera in his lineup, Bailey again made a strong impression in his new job, Although the 2002–03 season was cut short due to the Venezuelan general strike, Bailey set the tone for what’s turned out to be a legendary career in a place he calls one of his homes during the year.

“(I) just tried to do the best I could to learn the culture, said Bailey. “I was so focused on baseball my first year because I wanted to prove myself that there really wasn’t many distractions at the ballpark.

“You get wrapped up in it. In some stadiums, you might get 12–15,000 a night here and there, but when you get into the postseason and you’re playing in front of 18,000 or 25,000, that’s another element even for anybody that’s in the minor leagues. The whole city lives and dies with their team.”

Buddy Bailey is a legendary skipper in the Venezuelan Professional Baseball League (800Noticias)

It hasn’t all been easy to navigate. In November of 2011, Tigres’ catcher Wilson Ramos survived a two-day kidnapping before being rescued by authorities. One month later, tragedy struck in a more permanent form when relief pitcher Roseman Garcia passed away in an automobile accident.

“We had played a game in Caracas and his girlfriend was in,” Bailey said. “Instead of riding the bus, he was going to ride with them. Some of the players said, ‘Oh, just follow the bus,’ but he wanted to go. It was crazy because we were coming down a four-lane road and traffic stopped because there was a wreck. And we were probably 300 yards behind the accident, and a couple of players got off and wanted to go check it out. So they get out, walk there and they were crying because it was him, their teammate. And we were scheduled to play the next day. Obviously, the game was cancelled. The next day was going to be his funeral so we played a doubleheader. We needed to win some games and we did. It was really a sad moment, and I think he kind of looked over us to get us through all that.”

Through both of those heartbreaks, Bailey kept his team together. And somehow, Tigres de Aragua won the league’s championship that season.

Buddy Bailey is congratulated by his coaching staff after his 2,000th career victory. (Larry Kave/Myrtle Beach Pelicans)

“He has so much knowledge about this game that he can share with everybody and help us to succeed,” said Lopez, who has managed against Bailey in Venezuela. “I consider Buddy Bailey to be another Venezuelan citizen because he’s been going there, and he’s not afraid to go there. He loves our country. And to me, he’s a legend, and to a lot of people, he’s a legend.”

Through the good times and the bad, legend is a word that comes to mind from members of various front offices Bailey has worked in, his players and even his opponents.

“One word, just legend,” Minch said. “I think Buddy Bailey has a different demeanor about himself. He expects the best of you every time out. He has guys doing early work everyday, getting their mind right for the game, making sure you’re ready to play. We all have that one goal of playing in the Major Leagues. He does a great job at developing players and getting us to reach our dream.”

“Legend,” Pelicans outfielder Connor Myers said. “He’s at 2,000 wins, he has so much knowledge of the game, and he’s a good guy too. It’s really cool to play under Buddy.”

Buddy Bailey is 11th all-time according to Baseball Reference in minor league victories. (Larry Kave/Myrtle Beach Pelicans)

“Buddy helped show me the way because I came in as a rookie at the age of 40, and Buddy just kind of took me under his wing and said, ‘When it’s time to do this, you need to do this,’” Roberts said. “He was understanding, he helped me do that without being demanding and getting angry at me when I screwed up. He was great to work with both of those years. I enjoyed 1991, 1992 a lot.”

It’s an amazing emotion to feel like you’re right where you’re supposed to be, exactly when you’re supposed to be there. Baseball has an incredible way of making that happen. For Buddy Bailey it’s been a few decades of riding buses, winning championships and molding future big leaguer. A small-town Virginia boy has been all over the country and all over the world, and no matter where or when he there, he’s always in the right spot at the right time.

“I grew up old country boy in Virginia, and had to go mow the yard, and get the weeds out, and bale hay, and slop the hogs, and water horses and cows, and slop the pigs,” said Bailey. “I think it’s helped me though, because as a kid, it taught me you’ve got to go put in a day’s work.

“When I went to college and was getting a degree, I thought I was going to be a high school football or baseball coach. And then luckily that day came when Joe Torre called me and the Braves wanted me. I got to bypass a lot of that. I got into pro ball, right place and right time. I’ve been in three organizations that are really professional, top-of-the-line organizations that have treated me well. I hope I have given them the dividends back by busting my butt trying to help them develop the players and be contenders in the big leagues. So it’s a trade-off, and I’ve looked back and really can’t complain about any of it.”

The extraordinary moments are the ones before a game. The humidity’s dropped, the sun is splashed over the field and it feels like that perfect day for a ballgame. Buddy Bailey has just fine-tuned another swing, and that adjustment may help make a star of the future. But if you look closely, you might catch the faint smile of a legend, not just of the past, but one still of the present.