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Ryan Flaherty

Ryan Edward Flaherty (born July 27, 1986) is an American professional baseball coach and former who played eight seasons in (MLB). He currently serves as the bench coach for the Chicago Cubs. Flaherty was born in , and is the son of Ed Flaherty, a longtime head baseball coach at the who was inducted into the American Baseball Coaches Association Hall of Fame in 2005. At , he earned the Gatorade Maine Player of the Year award as a senior and was ranked the 141st-best professional prospect in the country by Baseball America. He attended , where he played under coach . Selected by the Chicago Cubs in the first round (41st overall) of the 2008 MLB Draft as a supplemental pick, Flaherty spent his early professional career in the Cubs' minor league system as a versatile infielder capable of playing second base, third base, and shortstop. In December 2011, he was chosen by the Baltimore Orioles in the Rule 5 Draft, leading to his MLB debut with Baltimore on April 7, 2012. Over his playing career from 2012 to 2019, Flaherty appeared in 547 games primarily with the Orioles (2012–2017), along with stints with the Atlanta Braves (2018) and Cleveland Indians (2019), batting .215 with 37 home runs and 142 RBIs while providing defensive utility across multiple positions. He participated in postseason play in 2012, 2014 (with the Orioles), and 2018 (with the Braves). Following his retirement from playing after the 2019 season, Flaherty transitioned into coaching, joining the Padres organization in December 2019 as a major-league advance and player-development coach. He quickly advanced to the role of bench coach for the Padres from 2020 to 2023, working under manager and later . In January 2024, Flaherty joined the Chicago Cubs under manager as their bench coach, a position he has held through the 2025 season. In 2025, Flaherty emerged as a candidate for several MLB managerial vacancies, including those with the San Diego Padres, Baltimore Orioles, and , though he remained with the Cubs after being passed over for the Padres role. His rapid rise in coaching ranks has been attributed to his playing experience, analytical approach to the game, and connections from his time in both the Cubs and Padres organizations.

Early life and education

Early life and high school

Ryan Flaherty was born on July 27, 1986, in , to parents Edward and Deborah Flaherty. His father, Ed Flaherty, served as the longtime head baseball coach at the , leading the Huskies for 39 seasons until his retirement in 2024 and winning two national championships. Growing up in a baseball-centric family, Flaherty developed an early passion for the sport through local youth leagues in and informal games with his siblings, including older sister and younger brother . Flaherty attended in , graduating in 2005 as a standout three-sport athlete in , , and soccer. During his high school , he excelled as a and , earning recognition as the High School Player of the Year in his senior season and ranking as the No. 141 high school prospect in the country by Baseball America. His defensive prowess and left-handed swing were highlights, contributing to Deering's undefeated season in 2004. Beyond high school, Flaherty achieved significant amateur success by leading the Nova Seafood team—composed largely of Deering players—to the 2004 Championship, the first national title for a team, where he also won the Telegram League batting title that year. Following his high school graduation, Flaherty continued his career at .

College career

Flaherty attended from 2006 to 2008, where he played for the as an . During his freshman season in 2006, he batted .339 with 49 , 19 doubles, and 2 home runs over 62 games, primarily splitting time between first base and while earning honorable mention Freshman All-American honors. In his sophomore year of 2007, Flaherty emerged as a standout, hitting .381 with 57 , 23 doubles, 3 triples, and 4 home runs in 67 games, primarily at . He was named a Second-Team All-American by both and the American Baseball Coaches Association (ABCA), as well as Second-Team All-, and contributed to Vanderbilt's SEC Tournament championship and No. 1 national seed in the NCAA Tournament. As a junior in 2008, Flaherty batted .324 with a team-high 63 , 14 home runs, and 10 doubles in 63 games, showcasing his infield versatility across second base, , and third base while serving as a semifinalist for the . Over his three seasons at , Flaherty compiled a .349 with 169 , 20 home runs, and 52 doubles in 192 games, demonstrating consistent production and defensive flexibility in the infield. His contributions helped the Commodores reach the NCAA Tournament each year, including regional victories in 2006 and 2007. Following his junior year, Flaherty decided to forgo his senior season and enter the 2008 MLB Draft, where he was selected by the Chicago Cubs as the 41st overall pick in the supplemental first round.

Professional playing career

Draft and minor leagues

Following a standout junior season at , where he batted .340 with 14 home runs and earned second-team All-American honors, Ryan Flaherty was selected by the Chicago Cubs with the 41st overall pick in the compensatory first round of the 2008 MLB Draft. He signed a contract with the Cubs that included a $906,000 . Flaherty's professional career began in 2008 with the Rookie-level in the , where he hit .297 with eight home runs in 56 games. He advanced to Single-A in 2009 with the of the , batting .276 with 20 home runs across 131 games while primarily playing and third base. In 2010, Flaherty progressed to with the Daytona Cubs of the before a midseason promotion to Double-A Tennessee in the Southern League, where he combined for a .271 average, 10 home runs, and 131 games, splitting time between second base and third base. The following year, he returned to the early in the season and earned a promotion to Triple-A of the in June, hitting .280 with 19 home runs in 132 games while continuing to showcase infield flexibility. Across his four seasons in the Cubs' system from 2008 to 2011, Flaherty played 450 games, batting .278 with 57 home runs and developing strong versatility across second base, third base, and . Following the 2011 season, as a Rule 5 Draft-eligible player on the ' roster, he was selected by the Baltimore Orioles with the third pick in the phase on December 8, 2011.

Chicago Cubs organization

Following his selection in the 2008 MLB Draft, Flaherty was initially assigned to the Chicago Cubs' Rookie-level affiliate, the of the , where he adapted quickly to . In 56 games that season, he posted a .297 with 8 home runs and 26 RBIs, primarily playing and showcasing solid contact skills early in his career. Flaherty progressed steadily through the Cubs' system over the next three years, demonstrating versatility across the infield. In 2009, with the Single-A , he hit .276 with a career-high 20 home runs and 81 RBIs in 131 games, splitting time between second base, third base, and while improving his defensive range at the corners. He advanced to Daytona in 2010, batting .286 with 9 home runs and 63 RBIs in 108 games, continuing to refine his glovework at multiple positions, before a brief stint at Double-A where he hit .183 in 23 games. By 2011, Flaherty reached Triple-A with the , hitting .237 with 5 home runs in 49 games, but his strongest performance came at Double-A , where he slashed .305/.385/.513 with 14 home runs and 66 RBIs in 83 games, expanding his defensive profile to include first base, left field, and right field alongside his infield roles. This multi-positional flexibility addressed earlier critiques of his range at and third base, positioning him as a option. No major injuries or setbacks were reported during Flaherty's Cubs tenure from 2008 to 2011, allowing consistent development. His 2011 campaign, particularly at Double-A, highlighted his power potential and adaptability, drawing attention from scouts and culminating in his exposure in the . Overall, his Cubs-affiliated stats from 2008 to 2011 included a .278 over 1,670 at-bats, underscoring his growth as a prospect.

Baltimore Orioles

Flaherty was acquired by the Baltimore Orioles through the on December 8, 2011, and was added to the team's 40-man roster to protect his eligibility. Following his development in the Cubs organization, he earned a spot on the roster as a utility infielder. Flaherty made his MLB debut on April 7, 2012, starting at second base against the . In his rookie season, he appeared in 77 games, batting .216 with 6 s and 19 while playing multiple infield positions. Key highlights included his first career , a on May 10 against the , which sparked the first three consecutive home runs to open a game in American League history, followed by those from J.J. Hardy and Nick Markakis. Later that year, on September 28, he hit his first career grand slam off Aaron Cook of the Boston Red Sox, driving in four runs during a 9-1 victory. In the postseason, Flaherty hit a two-run in Game 3 of the ALDS against the New York Yankees on October 10, becoming the first Maine native to record an MLB playoff . From 2013 to 2017, Flaherty served primarily as a versatile utility for , contributing to three playoff appearances while filling roles at second base, third base, , and occasionally . In 2016, he batted .217 with 3 home runs and 15 in 74 games, and on August 20, he made his only MLB pitching appearance, throwing one inning against the Houston Astros and allowing two earned runs. Ahead of the 2017 season, Flaherty agreed to a one-year worth $1.8 million, avoiding . That year, limited by injury, he played just 23 games with a .211 average before being in August. Over his six seasons with , Flaherty appeared in 452 games, batting .215 with 35 home runs—accounting for the majority of his career total of 37—and 128 . He was granted free agency on November 2, 2017, concluding his tenure with the organization.

Philadelphia Phillies

Following his non-tendering and subsequent free agency from the in November 2017, Ryan Flaherty signed a minor league contract with the Phillies on February 9, 2018, which included an invitation to and a potential $1.9 million if added to the 40-man roster. During , Flaherty received limited opportunities to showcase his skills, appearing in 18 games with 37 at-bats while providing defensive reps primarily at second base, third base, and to demonstrate his utility infielder versatility. His performance did not stand out sufficiently to earn a roster spot amid competition from established players and younger prospects vying for infield positions. On March 22, 2018, the Phillies granted Flaherty an unconditional release after he exercised an clause in his contract, ending his brief stint with the organization without any games played. This marked a transitional low point in Flaherty's career as he sought opportunities elsewhere following four seasons with .

Atlanta Braves

Following his release from the Philadelphia Phillies during , Flaherty signed a one-year contract with the on March 26, 2018, valued at $750,000. Flaherty served as a utility for the Braves, providing defensive depth across multiple positions during the 2018 season. He appeared in 81 games, primarily at third base (40 games), with additional starts at first base (7 games) and second base (1 game). His versatility allowed manager to deploy him as a late-inning replacement and occasional starter amid injuries and roster adjustments. At the plate, Flaherty batted .217 with 2 home runs and 13 in 161 at-bats, offering left-handed power off the bench during the Braves' East-winning campaign. Early in the season, he contributed to Atlanta's strong start with a .308 over his first 24 games, helping stabilize the lineup as the team pushed toward the . The Braves qualified for the postseason as division champions, though Flaherty was on August 20 before being recalled from Triple-A Gwinnett on September 2. Flaherty's contract expired at season's end, and the Braves non-tendered him on October 29, 2018, making him a free agent.

Cleveland Guardians

On February 7, 2019, Flaherty signed a minor league contract with the Cleveland Indians, which included an invitation to Major League Spring Training, marking his final professional playing agreement after spending the previous season with the Atlanta Braves. Flaherty spent most of the 2019 season in Triple-A with the , appearing in 113 games where he batted .263 with 19 home runs and 73 . In 2019, he appeared in 14 games for the Indians (now known as the Guardians), making his last appearance on September 29, 2019, against the Boston Red Sox, going 0-for-3 at the plate. Following the 2019 season, Flaherty retired from playing after a 10-year career, during which he compiled a .215 , 37 home runs, and 142 across 547 games.

Coaching career

San Diego Padres

Flaherty joined the Padres organization on November 24, 2019, as a advance scout and development coach, marking his transition from playing to coaching. In this initial role, he focused on player development and the integration of to support the major league team, drawing on his eight years of professional playing experience across multiple positions. He was promoted to ahead of the 2022 season, continuing to contribute to game planning and development efforts. On , 2022, Flaherty served as acting manager for the Padres' game against the Colorado Rockies, stepping in due to manager Bob Melvin's placement on the ; he went on to manage a total of 10 games during Melvin's absence from to June 21. During his time in development and quality control roles, Flaherty emphasized infield coaching, utilizing his background as a utility to mentor players on positional fundamentals and . Flaherty received a further promotion to bench coach and on February 3, 2023, entering his fourth season with the staff. Following the 2023 season, he departed the Padres to join the Chicago Cubs as their bench coach.

Chicago Cubs

Ryan Flaherty was hired as the bench coach for the Chicago Cubs on January 2, 2024, joining manager Counsell's inaugural staff after serving in a similar role with the San Diego Padres the previous season. In this position, Flaherty assists with in-game strategy, player development, and infield instruction, focusing on defensive techniques and positional flexibility for infielders. During the 2024 season, the Cubs finished with an 83-79 record, securing second place in the but falling short of the . Flaherty contributed to the team's preparation and adjustments throughout the year, helping to integrate young players into the lineup amid a competitive division race. The following year, in 2025, the Cubs improved to a 92-70 mark, again finishing second in the NL Central and earning a spot before losing 3-2 to the Brewers in the . His work supported the development of key infield contributors, enhancing the team's overall defensive versatility. In October 2025, following the Cubs' postseason exit, Flaherty emerged as a candidate for managerial positions with the Baltimore Orioles and Padres, conducting interviews for the latter vacancy. Ultimately, he was not selected for either role and remained with the Cubs as of November 2025. Drawing from his as a utility who appeared at second base, third base, and across 315 MLB games, Flaherty's philosophy prioritizes versatility, encouraging players to master multiple positions to maximize roster utility.

Personal life and legacy

Personal life

Flaherty married Dutko, an American lawyer, on December 10, 2016, in . is the sister of Christina Dutko, the wife of former MLB outfielder , establishing a family connection between the two players as brothers-in-law. The couple welcomed their first child, a son named Ryan Jr., on October 1, 2019. Flaherty, who was born and raised in Portland, Maine, has maintained personal ties to the state through his family background.

Legacy

Ryan Flaherty holds a pioneering place in Major League Baseball history as the first player born and raised in Maine to hit a home run in the postseason. This milestone came during Game 3 of the 2012 American League Division Series against the New York Yankees, where his two-run homer off CC Sabathia helped the Baltimore Orioles secure a 2-1 victory and extend their improbable playoff run. Flaherty's contributions that year, including a grand slam against the Boston Red Sox on September 28 that clinched a key win during the Orioles' late-season surge, underscored his role in ending Baltimore's 14-year postseason drought and providing essential depth as a Rule 5 Draft pick. Throughout his playing career, Flaherty exemplified versatility, appearing at every infield position and both corner outfield spots, while making one pitching appearance in 2016 for . This adaptability allowed him to contribute across multiple teams, including stints with the , , and Cleveland Indians, where he provided reliable defensive support and occasional offensive sparks in utility roles. Flaherty's transition to coaching highlighted his influence on player development and analytics-driven strategies. After retiring, he joined the Padres in 2019 as a major-league advance and player-development coach, serving as from 2020 to 2022, where he oversaw offensive game planning and . He became their bench coach in 2023. In 2024, he moved to the Cubs as bench coach under , emphasizing data-informed approaches to skill enhancement and in-game decision-making drawn from his utility-player experience. By 2025, Flaherty's emerging legacy included strong consideration for several managerial positions, positioning him as a respected figure in operations. He was a leading candidate for openings with the Baltimore Orioles, Padres, , and , reflecting his reputation for analytical acumen and developmental expertise, though he ultimately returned to the Cubs staff.

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