Some of Cubs bench coach Ryan Flaherty’s earliest baseball memories come from joining his dad and the University of Southern Maine baseball team on their annual spring trip to Florida.
Ed Flaherty, who since has been inducted into the American Baseball Coaches Association Hall of Fame and amassed a laundry list of coaching awards in his 39 seasons at the helm for the Huskies, already had built an impressive résumé in those early years leading the Division III program.
Before the weather finally turned in the Northeast, the team would head south for baseball weather and a packed schedule.
“Spending 12 hours a day at the field, doubleheaders, eating at concession stands, just sitting in a college dugout,” Ryan Flaherty reminisced in a conversation with the Sun-Times
Young Ryan would serve as the batboy. And between games of doubleheaders, his grandfather Ed Sr. would sometimes take him to the Red Sox’ spring-training-complex parking lot in Fort Myers to seek autographs.
Looking back now, Ryan can see how much of an impact baseball had on his family. Many of the collective memories are tied to the sport.
Ryan now is generally viewed in the industry as a future major-league manager. And before joining Craig Counsell’s coaching staff entering the 2024 season, he was a finalist in the Padres’ managerial search.
But Ryan never felt pushed into baseball, even as the son of a highly regarded coach.
“I always just would really watch,” Ryan said. “And I’d ask questions, like, ‘Why did this happen? Why did that happen?’ But he never really coached me, per se. It was just the environment I was in.”
The environment
Ed, who’s in the University of Maine Sports Hall of Fame for his college baseball career, grew up playing every sport available to him and wanted the same for his children.
“I just knew the value of sport,” he said, “what it brought to the table for kids, the people you get to meet, the lessons you learn.”
In addition to baseball or softball, the three Flaherty children — Regina, Ryan and Regan (who would go on to be drafted by the Mariners in 2009) — all played some combination of basketball, football and/or hockey.
From years of hanging out at the University of Southern Maine baseball field — now named after Ed Flaherty — and the fieldhouse during the colder months, Ryan picked up tips from players as he mixed in during station work.
Finally, when Ryan was in high school, Ed let him stand in against live pitching — specifically, two-way player Adam Lemieux.
“First pitch the kid threw, Ryan hit a line drive,” Ed said. “I said, ‘Oh, God, he almost knocked my No. 1 pitcher out.’ So that’s when you started to think, ‘He’s all right; he’s pretty good.’ ”
College ball
Even with Ed Flaherty’s institutional knowledge, it was hard to pinpoint his son’s baseball potential.
“He was tall, he was lanky; as a coach, you could say this kid moves well,” Ed said, noting a poor 60-yard dash time in Ryan’s first Perfect Game event his sophomore year. “He looked like Bambi. His legs looked way bigger than his upper body.”
After a couple of showcases the next year, however, the calls started pouring in from college programs. Ed and Deborah kept every letter their son received from a coach, Ryan said. They still have a bucket of them.
At the time, Vanderbilt wasn’t the baseball juggernaut it is now, thanks to coach Tim Corbin. He was just a couple of years into his tenure then, and Ryan was getting scholarship offers from bigger programs.
Ed had several connections to Corbin, including then-Clemson coach Jack Laggett, whom Corbin coached under and Ed played with in college.
He recalls Corbin coming out to Corvallis, Oregon, for a week to watch Flaherty’s team in the American Legion championship.
“He says, ‘Eddie, I think he’s going to be a major-league third baseman,’ ’’ Ed recalled. “I said, ‘Really, wow.’ And then he offered him a very good scholarship, more than the others.”
An official visit sealed the deal.
In Flaherty’s three years with Vanderbilt, the Commodores began a streak of consecutive NCAA Tournament appearances that stretched to 19 this season, and they claimed the 2007 SEC regular-season and tournament titles.
When Vanderbilt was eliminated in the 2008 regional, Flaherty returned home to Maine to gather with friends and family, including his grandfather Ed Sr., for the draft.
The Cubs selected Ryan No. 41 overall.
“It was just surreal,” Ryan said.
Coaching tradition
Ryan Flaherty has a simple way of explaining his career change, once the playing opportunities dried up after eight major-league seasons.
“I knew I wanted to stay in baseball, and coaching was a way to stay in baseball,” he said.
When Ryan told his dad he was thinking about coaching, Ed’s reaction was: “Geez, that’s a long track, minor leagues and all.”
Ryan had a different route in mind.
He caught on with the Padres in December 2019 as a major-league advance scout/player-development coach. And by 2023, he had climbed to bench coach.
As Ryan’s coaching career was taking off, Ed’s was winding down.
Ed retired last year. Southern Maine honored him in late April, and the timing couldn’t have been better for Ryan. The Cubs happened to be playing that evening at Fenway Park. Counsell gave the OK for Ryan to drive up for the ceremony.
Family, colleagues and generations of former players gathered to celebrate Ed Flaherty’s legendary career.
“Ryan made some nice statements,” Ed said, “because Ryan grew up kind of playing on that field himself.”
In the year since, Ed has taken advantage of the extra time to golf, help out with the All-Star team for one of his nearby grandchildren and visit his sons out of state.
Ed joined Ryan on the Cubs’ trip to Tokyo in March, and he was set to visit Chicago this weekend for Father’s Day.
The two talk after Cubs games all the time, sharpening each others’ thought processes with a generational difference in styles. The Cubs’ use of an opener in select games this season provided fertile ground for conversation.
“It’s almost like a complete circle,” Ryan said. “As a kid, I’m 9 years old asking why this guy runs out for a cutoff man instead of the other guy, and having him explain it. Now he’s trying to figure out why the heck we’re pitching one pitcher in the first inning and that’s it.”
Said Ed: “I don’t understand guys coming out in the fifth inning all the time, but that’s the way of the world.”
Ryan is now a father himself. He and his wife, Ashley, have three kids: Ryan Jr., 5, Jade, 3, and Julian, 1. Junior’s interest in baseball is already showing.
“You watch him watch practice, and you’re like, ‘OK, I remember doing that,’ ’’ Flaherty said.
As Junior gets older, Ryan is faced with the decision of how much he wants to coach his son. He’ll find himself tempted to intervene, and a memory with his dad will stop him.
“He’ll figure it out,” Ryan said. “You just try to expose him to it. And if he likes it, he likes it. If he doesn’t, he’ll find something he likes.”