Derrick May – Baseball Player Biography, Career, Net Worth Information

Derrick May’s baseball journey lasted a decade in the major leagues, mostly with the Chicago Cubs from 1990 to 1994 before he moved on to the Milwaukee Brewers and Houston Astros. This left-handed outfielder, born July 14, 1968, in Rochester, NY, retired from Major League Baseball in 1999 at age 31, wrapping up a career that highlighted his 6’4″ build and steady left field play. At 210 pounds, May brought some real power potential to every team he joined.

After wrapping up his MLB days, May couldn’t just walk away from baseball. He poured his energy into a second act—this time as an international player and later as a coach. May’s post-playing career is really a story of passion, resilience, and dedication, the kind you don’t always hear about when folks look back at players who never became superstars but still made a mark on America’s pastime.

Derrick May’s Baseball Career Overview

Derrick May spent ten years in Major League Baseball from 1990 to 1999, suiting up for six different teams and finishing with a solid .271 lifetime batting average. His climb from first-round draft pick to major leaguer says a lot about the grit it takes to stick around in pro baseball.

Early Life and Background

May was born July 14, 1968, in Rochester, New York. He sharpened his baseball skills at Newark High School in Delaware. Even back then, his talent jumped out—major league scouts took notice.

The Chicago Cubs drafted him 9th overall in the first round in 1986, a pick that showed just how much potential they saw in him.

He didn’t rocket straight to the majors. May spent several years grinding in the Cubs’ minor league system, working on his swing and outfield defense before finally getting his shot.

The Cubs saw enough in his minor league performance to call him up, and he made his MLB debut soon after.

Major League Baseball Debut

Derrick May stepped onto a Major League Baseball field for the first time on September 6, 1990, with the Chicago Cubs. That debut delivered on the promise scouts saw when they drafted him four years earlier.

He spent his first five big league seasons (1990-1994) with Chicago, carving out a role as a steady contributor. During that run, May proved he could hit at the highest level.

After Chicago, his journey got a bit more unpredictable. He played for the Milwaukee Brewers in 1995, then moved on to the Houston Astros, Philadelphia Phillies, Montreal Expos, and finally, the Baltimore Orioles.

May played all three outfield spots when his teams needed him to. He kept his batting average around .271, making himself a valuable role player wherever he went.

Retirement in 1999

May played his last MLB season in 1999, capping off a decade in the majors. When he retired, he’d posted a .271 batting average over parts of 10 seasons with six different teams.

He didn’t step away from the game, though. May jumped into coaching, using everything he’d learned as a player to help up-and-coming hitters.

He held coaching jobs with different organizations, a testament to the respect he earned on the field. May’s baseball know-how has served him well since hanging up his cleats.

Teams and Notable Tenures

Derrick May’s MLB career stretched across six teams in ten years, with his best numbers coming early on. He showed versatility as an outfielder and pinch hitter in both the National and American Leagues.

Chicago Cubs Era

May’s pro career kicked off when the Chicago Cubs picked him in the first round (9th overall) of the 1986 MLB Draft. After working his way up through the minors, he debuted on September 4, 1990.

By 1991, May became a regular for the Cubs, mostly playing the outfield and showing off his steady bat and reliable glove.

His standout season in Chicago came in 1993, when he set career highs in several offensive categories. That left-handed swing brought some balance to the Cubs lineup in those early ’90s years.

During his five seasons with the Cubs (1990-1994), May proved himself as a dependable outfielder who could hit for average. His time in Chicago was easily the most stable and productive stretch of his MLB career.

Baltimore Orioles Contributions

May’s big league run ended with the Baltimore Orioles in 1999, not far from his high school days in Newark, Delaware.

By then, he played mostly off the bench and filled the pinch-hitting role. Even if his stats with Baltimore weren’t eye-popping, May brought a veteran presence and helped mentor younger players.

He understood hitting mechanics and always took a professional approach, earning respect in the clubhouse.

That stint with the Orioles closed the book on his MLB playing days, and soon after, he pivoted to coaching.

Playing for the Houston Astros

May joined the Houston Astros for parts of two seasons (1995-1996). He took on the role of utility outfielder and pinch hitter.

While in Houston, May contributed to an Astros squad that was starting to build toward being a contender. His managers plugged him into multiple outfield spots as needed.

The Astros counted on his professional approach at the plate and his knack for handling pitchers from both sides. He wasn’t an everyday starter, but his work off the bench added important depth.

May’s time in Houston was short but showed his adaptability and willingness to take on whatever job the team needed. That flexibility became a theme for him as his career went on.

Milwaukee Brewers Stint

May’s stretch with the Milwaukee Brewers in 1995 didn’t last long, but it marked a turning point. After leaving the Cubs, he landed in Milwaukee before heading to Houston that same season.

With the Brewers, May continued to show what he could do as a left-handed outfielder, even in a part-time role. He stayed consistent and professional, even with limited at-bats.

He didn’t put up huge numbers in Milwaukee, but he did his job. The Brewers saw his ability to adjust, and he quickly fit in with new teammates and coaches.

That experience with the Brewers showed just how quickly May could get comfortable in a new setting—a skill that helped him as he moved around later in his career.

Transition Between Leagues

Derrick May’s career took him through both the National and American Leagues, and each stop brought new experiences and challenges.

National League Experiences

May started with the Chicago Cubs (1990-94), where he made his mark as a reliable outfielder. His batting average during those years showed his potential, and he became a steady presence in the lineup.

When he joined the Milwaukee Brewers in 1995, he had to adjust to a new clubhouse and routine. That move was followed quickly by a trade to Houston.

He also spent time with the Philadelphia Phillies, mostly as an outfielder and pinch hitter. Through all these National League stops, May stuck to his approach at the plate, using his size to generate some power.

American League Performances

May didn’t play in the American League until later in his career, when he signed on with the Baltimore Orioles. That switch forced him to adjust to different pitching and the challenge of facing lineups with designated hitters.

The American League ballparks had their own quirks—different field dimensions, turf, and even the vibe. May had to tweak his defense and how he approached the game.

Still, he used his experience as an outfielder and pinch hitter to stay valuable, no matter which league he played in.

May’s career batting average of .271 across both leagues shows just how steady he was, even as he bounced between teams and ballparks.

Career Achievements and Highlights

Derrick May’s MLB career might not have been filled with headlines, but he consistently produced on offense and always gave his teams a reliable outfield option. He built a reputation as a solid pro who just kept grinding.

Batting Average and Offensive Production

Throughout his time in the majors, May kept a .271 career batting average over 797 games. That kind of consistency at the plate isn’t easy to find. He actually out-hit quite a few guys from his era.

He put up a .319 on-base percentage and .398 slugging percentage, which shows he could get on base and offer some pop, too. Those numbers kept him in major league lineups for a decade.

All told, May’s professional career spanned 18 years, with 10 of those in the big leagues. That’s a long time to stay in the game, and it says a lot about his work ethic.

Home Runs and Doubles

May had some power, but he wasn’t really a home run hitter. Over his MLB career, he hit 52 home runs, averaging about 5-6 per full season.

He made up for it with gap power, driving the ball for doubles and keeping his slugging percentage just under .400.

After his major league days, May kept playing in pro ball, including a run with the Cook County team in the Frontier League in 1999, which turned out to be his last season as a player.

Runs Batted In and Runs Scored

May knew how to drive in runs. He finished with 310 RBIs in his MLB career, which shakes out to about 31 RBIs per season, considering his playing time.

He helped his teams score in other ways, too. May’s knack for getting on base meant he could help manufacture runs, not just drive them in.

After retiring as a player in 1999, May started coaching and eventually managed the Frederick Keys in the Draft League in 2021. He kept giving back to the game, working with young players and sharing what he’d learned.

Notable Moments and Milestones

Derrick May’s ten years in the majors included some memorable performances—big games, clutch hits, and a few home runs that fans still remember. Whether he was with the Cubs, Brewers, Astros, Phillies, Expos, or Orioles, May always seemed to find a way to make an impact.

Key Games and Series

Back in 1992, May put together one of his best seasons with the Chicago Cubs, batting a career-high .295 and knocking out 33 doubles. That August, he really stepped up during a tense four-game set against the St. Louis Cardinals. In the final game, he drove in five RBIs, helping the Cubs dodge a sweep.

May’s versatility really showed in a 1994 game at Yankee Stadium with the Expos. Even with the crowd buzzing, he picked up three hits and made a diving catch in right field that landed him on a few highlight reels.

He also had a huge day in 1993 against the Phillies—ironically, before he’d later join them—going 4-for-5 with 6 RBIs and missing the cycle by just a triple.

Memorable Home Runs

May wasn’t exactly famous for his power, but he still managed 52 home runs in his major league career. The most dramatic? In 1992 with the Cubs, he smashed a walk-off grand slam against the Pirates, flipping a two-run deficit into a win.

In a 1995 interleague game, May launched a 450-foot home run that cleared Milwaukee’s County Stadium scoreboard—pretty impressive for someone known more for contact than power.

His last big league home run came in 1999 with the Orioles—a fitting farewell at Camden Yards that helped Baltimore top the Yankees. That shot capped off a professional career spanning 31 years as both a player and coach.

Teammates and Influential Figures

During his decade in the majors, Derrick May crossed paths with all sorts of teammates and baseball greats who left their mark on his journey.

Teaming Up with All-Stars

While May played for the Houston Astros (1995-96), he shared the outfield with some big names. He got to play alongside Jeff Bagwell, who was already making a name as one of the top first basemen.

The Astros roster also featured Moises Alou, whose bat and steady defense fit right in with May’s style. Kevin Bass was another veteran presence, offering leadership during May’s time there.

With the Cubs (1990-94), May came up alongside several young players who’d go on to be All-Stars. Those relationships influenced his approach and gave him some much-needed mentorship early on.

Connections with Baseball Legends

May’s path through baseball put him near plenty of legends. In his final MLB season with the Orioles in 1999, the club still felt the influence of guys like Jose Cruz, who set a high bar for outfielders.

He often talked about studying the swings and routines of icons like Babe Ruth and Lou Gehrig, trying to pick up whatever he could from their dedication and skill.

After hanging up his cleats, May spent 15 years coaching, passing on what he’d learned from his own experiences and the greats he’d played against—guys like Jorge Posada during interleague games.

Roster Changes and Late Career Moves

In the last stretch of his MLB career, Derrick May bounced between teams, trying to find a steady spot as free agency and roster moves became the norm. Things shifted a lot after he left the Cubs.

Free Agency and Re-signings

May hit free agency for the first time after the 1994 season, leaving the Chicago Cubs after five years. The Milwaukee Brewers picked him up for 1995, but that didn’t last long.

After just one season in Milwaukee, he headed to the Houston Astros in 1996. His ability to play all over the outfield made him useful as a utility player, though his bat wasn’t quite what it used to be.

The Phillies brought him in for 1997, keeping his National League journey going. Most of his contracts at this point were one-year deals, which says a lot about the uncertainty he faced as his career wound down.

Released, Waivers, and Minor League Contracts

After 1997, May’s career got tougher. He landed with the Montreal Expos in 1998, but they released him, and the Orioles picked him up.

By 1999, he was mostly signing minor league deals as big league chances slipped away. He retired in 1999 after being granted free agency in October and then signing with the Orioles that November.

In those last years, he cleared waivers more than once and took assignments to Triple-A teams. That’s the reality for a lot of veterans in their 30s—more depth piece than everyday starter.

Once his playing days ended, May jumped into coaching, joining the Palm Beach Cardinals (Low-A St. Louis) in 2005 and 2006.

Role and Position Analysis

Derrick May spent most of his MLB career as an outfielder, moving around the outfield as needed. At 6’4″ and 210 pounds, he really looked the part.

Right Field Responsibilities

He spent a lot of time in right field, where his strong arm helped cut down runners trying to stretch hits. He had to cover a lot of ground and make quick throws to keep doubles and triples in check.

Right field’s not easy—it takes good instincts and the ability to read balls off the bat, not to mention dealing with tricky sun angles during day games.

May backed up throws to first and served as a cutoff for plays at the plate. His experience helped him anticipate where balls would land, which made his positioning pretty sharp.

Utility and Defensive Skills

May didn’t just stick to right field. He filled in as a utility outfielder, playing left field and occasionally stepping in elsewhere. Teams like the Cubs and Brewers valued that flexibility.

His defense was solid—good range, steady hands. He wasn’t known for flashy defense, but his fielding percentages held up.

As a pinch hitter, May gave teams a lefty bat off the bench when the game was on the line. That takes a lot of mental toughness, especially when you’re not getting regular at-bats.

His size and strength helped him handle the grind of the outfield, even when the weather turned rough or the season dragged on.

Career Comparison and Legacy

Derrick May’s MLB career stands out for its consistency and adaptability. When you look at his stats and style, there’s a lot to learn by comparing him to other outfielders from the ‘90s.

Comparison with Contemporary Players

Compared to other outfielders of his time, May’s .271 career batting average holds up respectably. He landed somewhere in the middle tier for outfielders in the ‘90s.

He wasn’t a headline-making power hitter—his 52 home runs and 310 RBIs in 797 games show he leaned more towards contact hitting than slugging. Left fielders like Barry Bonds and Albert Belle put up bigger power numbers, no doubt.

What really stands out is May’s durability. He played pro ball for 18 years, showing impressive longevity. Drafted by the Cubs as their first-round pick (9th overall) in 1986, he stuck around thanks to steady play, not flashy moments.

Impact on MLB History

May’s MLB legacy shows just how important utility outfielders and pinch hitters were during the high-offense ‘90s. His .319 on-base percentage speaks to his knack for getting on base.

He played for a bunch of teams—Cubs, Brewers, Astros, Phillies, Expos, Orioles—showing the typical path of guys who provide important depth for contenders.

May’s baseball knowledge didn’t fade after he retired. He moved into coaching and player development, helping shape new generations of players.

Looking at MLB history, May represents the kind of steady, reliable player who kept teams going, even if he didn’t make headlines or stir up controversy.

Related Teams and Associations

Derrick May’s baseball career took him all over, from the majors to the minors and even overseas. He bounced between organizations, carving out a role as a journeyman outfielder with major league experience.

Other Major League Teams

May started out with the Chicago Cubs (1990-1994), then moved to the Milwaukee Brewers in 1995 for a short stint before a trade sent him to the Houston Astros, where he played through part of ‘96.

He signed with the Philadelphia Phillies for the 1997 season, spent a year with the Montreal Expos in 1998, and wrapped up his big league run with the Baltimore Orioles in 1999.

He never suited up for the Boston Red Sox, Seattle Mariners, Tampa Bay Devil Rays, Pirates, Texas Rangers, or Atlanta Braves, but he saw plenty of them from the other dugout.

Brief Stints and Minor Associations

May’s journey didn’t end in MLB. He played for the Chiba Lotte Marines in Japan, adding an international chapter to his baseball story.

After his playing days, he switched to coaching. He started with the Palm Beach Cardinals (Low-A St. Louis) in 2005 and 2006 as a hitting coach, kicking off his coaching career.

From 2007 to 2010, May continued coaching in the Cardinals organization, using his experience to help develop young players.

He eventually returned to the Frederick Keys, but this time as a manager, leading them in their first Draft League season. That move really showed his dedication to mentoring young talent and giving back to the sport that shaped his life.

After Baseball: Life Post-Retirement

After retiring from pro ball in 1999, Derrick May jumped into coaching and kept making an impact on the game he loved.

Involvement in 2014 Season and Beyond

After hanging up his cleats, May didn’t wander too far from the diamond. He started coaching with the Palm Beach Cardinals (Low-A St. Louis) for the 2005 and 2006 seasons. From there, he kept at it and coached on staff from 2007 through 2010.

In 2014, May really dove into player development. He leaned on his decade of Major League experience, especially when working with young outfielders. You could see how much his guidance mattered as he helped them sharpen their skills.

Fast forward to 2021, and May finally got his shot at managing. The Frederick Keys named him manager in the new MLB Draft League. After years of coaching, this was his first official gig as a manager—a big moment for him.

Community Impact and Coaching

May hasn’t just stuck to pro teams since retiring. He’s spent a lot of time working with young talent at baseball camps and clinics. With 31 years in professional baseball as both a player and coach, he’s got plenty of stories and advice to share.

At The Baseball Warehouse, May works as an instructor, helping up-and-coming players get better at the game. He doesn’t just teach technique—he digs into the mental side of baseball too.

His coaching philosophy comes straight from his days as an outfielder with teams like the Chicago Cubs, Milwaukee Brewers, and Houston Astros. He wants to develop well-rounded players who know the fundamentals and can handle any situation on the field.

May’s journey from player to coach isn’t unusual, but he’s made it work. He’s found a way to stay close to the sport he’s always loved.

Derrick May’s Place in Baseball History

Derrick May, a left-handed outfielder from the 1990s, carved out a pretty solid niche in baseball history. The Chicago Cubs picked him 9th overall in 1986, and honestly, he kind of embodied that era’s typical “highly-touted prospect” vibe.

He played parts of 10 seasons in the majors, mostly with the Cubs from 1990 to 1994. After that, he bounced around a bit—spent time with the Milwaukee Brewers, Houston Astros, and a few other teams before calling it quits in 1999.

May fits right in with a crowd of talented outfielders from the 1990s baseball landscape. He never quite hit superstar status, but sticking around for a decade took grit and a knack for adapting—qualities you really need if you want to survive in professional baseball.

Standing 6’4″ and weighing in at 210 pounds, May had the physical attributes scouts drool over. With his left-handed bat, he brought value to several National League clubs over the years.

After hanging up his cleats, May jumped into coaching and just kept going. It’s a path you see a lot—former players sticking around and giving back to the game.

You won’t find May’s name alongside the legends, but he’s a perfect example of those essential pros who kept the competitive standard high in 1990s baseball. His story highlights how tough it is to break through to stardom in pro sports.

With 31 years in professional baseball as a player and coach, May’s commitment to the game goes way beyond just his playing days.