Win No. 500 — How the Holliday Name Became Synonymous With OSU Baseball

On a balmy November 2025 afternoon, Tom Holliday sat in the press box at O'Brate Stadium, watching practice unfold.

In an adjacent booth sat his granddaughter, Olivia Holliday, and former Oklahoma State baseball coach Gary Ward, the two talking as batting practice carried on below. Tom's gaze drifted between them and the field, never straying too far from either.

For Tom, it was an ideal day.

Baseball is a vital element of the Holliday family identity and has been for more than 50 years. That was the case for Tom in his near-two decades as OSU's pitching coach. And again during his seven seasons as Ward's successor. Now, head coach Josh Holliday, father of Olivia, is in his 14th season at the helm of the program, carrying on the family legacy.

"I'm sitting there thinking, where did the time go? Where did it all go?" Tom said in a phone interview with The Stillwegian. "I had a good time at OSU, had a good time at Texas, had a good time at Auburn and then Josh got the (head coaching job) here and all of a sudden you're back, and it's like you never left.

"Coach Ward is 85, he's the same guy he was when he was 50. Josh is 49, almost 50, and he's just about the same person he was when he was a ballplayer here. You sit here and you reminisce and it's like, damn, it's been that long?"

Forty-nine years separates the family's arrival in Stillwater and the present. Yet, through all the highs, sentimental moments and accomplishments that have come along the way, watching Josh build OSU baseball into its modern form has been most fulfilling, he said. And on Tuesday, Josh reached a monumental landmark in his coaching tenure.

OSU run-ruled Wichita State 14-4 in seven innings at O'Brate Stadium, giving him his 500th win as head coach. Through 14 years and 778 games, he'd already established himself as the program's second-winningest coach, only behind Ward. His 779th, however, cemented his name within program lore.

"It's gone fast," Josh said. "It's hard to believe how fast time is expiring."

OSU head coach Josh Holliday poses for a portrait in the dugout at Allie P. Reynolds Stadium in Stillwater on July 5, 2012, ahead of his first season leading the program. – Photo Courtesy OSU Athletics

Josh, like Tom, finds time less a measure of years passed than a blur of innings lived. But to program delegates and former proteges and players, Tuesday's milestone was a long time coming.

"It's awesome," OSU sophomore shortstop Brock Thompson said. "...It's just been awesome to play with everyone and learn so much. You know, (it was) awesome to play my freshman year to this year, and he's just helped me tremendously."

Stillwater raised Josh. OSU baseball provided him an identity.

A successful four-year playing career at OSU gave him clarity on his life goal. By the time he had exhausted eligibility in 1999, he knew he wanted to be a head coach. But to fulfill that, he had to start elsewhere.

So, he went outside Stillwater. Along the way came assistant coaching stints under baseball legends — Arizona State's Pat Murphy, now manager of the Milwaukee Brewers, North Carolina State's Elliott Avent, Georgia Tech's Danny Hall, and Vanderbilt's Tim Corbin — which provided him knowledge and experience that morphed him into a seasoned veteran within the coaching ranks.

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Then came his defining moment — a head coaching stint at his alma mater.

Success has come at large for OSU under Josh, but the lessons learned along the way are what he said he relishes the most. And carrying on his family's name at the program he cares for dearly is merely a crowning glory for him and everything in between.

"I don't think I've had a bad day in 14 years since I've been back," Josh said. "I know I never had a bad day when I was a kid, and I know I never had a bad one in the four years I got to play here. So, it's just joy. You love something, you care about it, you work at it, you pour yourself into it, you empty your tank every single night and you fight like crazy to protect it and make it better."

Stillwater, 1977

Something about Tom appealed to Ward.

He couldn't ascertain precisely what it was. It was just something about him.

Whether it was Tom's knowledge of the sport, his work ethic or even the charm he displayed with confidence when he walked into a room, Ward said he was sold the moment of their first encounter.

Tom showcased such qualities when Ward recruited him out of high school to Yavapai Junior College. That impression was only solidified during Tom's two-year playing career under Ward as a pitcher before transferring to Miami.

"I think I saw Tom's leadership qualities the moment he set foot on campus," Ward told The Stillwegian. "He was a baseball mind and you could just tell Tom knew what he was doing."

Former OSU head coach Gary Ward (left) and former OSU pitching coach Tom Holliday (right) during their time with the Cowboys program. Ward and Holliday guided OSU to 10 College World Series appearances, including seven straight from 1981-87. – Photos courtesy of OSU Athletics

So, when Ward was offered the head coaching position at OSU in 1977, he hadn't a second thought toward who his pitching coach would be.

"Tom was the leading candidate to come with me because I knew he wanted to coach," Ward said. "He was in it for the right reason. That was obvious."

Tom accepted without hesitation. And from that moment, the Holliday family legacy was born.

Tom moved to Stillwater in August 1977, bringing his wife Kathy. An 11-month-old Josh came in tow.

The first impression of the home confines? Uninspiring.

The baseball diamond was scarcely visible. A chain-link fence snaked around the outfield. Dugouts were covered with splinters and splits of wood pointing outward. The infield dirt was rough and bumpy. A pile of dirt had been dumped on the grass, but clearly not recently, given herds of sprouts and weeds were growing every which way out of the pitcher's mound.

But Ward and Tom made it work. On a low salary and amid each unideal element of the job in its infancy stages.

Tom spent 19 seasons (1978-96) as the Cowboys' pitching coach under Ward, and OSU baseball swiftly evolved into a household college baseball brand. The tandem put the program on the map, guiding it to 10 College World Series appearances — including seven straight from 1981-87, a standing NCAA record — three runner-up finishes and a treasure trove of conference championships.

📈

Josh Holliday – by the numbers: 14 : Number of seasons Holliday has been OSU’s skipper. He is the third-longest tenured coach in program history, behind Gary Ward (19) and Toby Greene (21).

779 : Number of games Holliday has coached at OSU (as of April 22, 2026)

12 : Number of consecutive regional appearances for OSU under Josh Holliday. The Cowboys are one of five programs nationally to appear in a regional each season since 2013, joining the likes of college baseball titans Vanderbilt, Louisiana State, Florida and Dallas Baptist.

5 : Conference championships during Holliday’s tenure. Three via conference tournament. Two in the regular season. OSU has finished second in the conference standings seven times under Holliday and been a runner-up in the tournament four times.

17 : All-Americans coached by Holliday.

77 : MLB Draft picks produced by Holliday. Three have been first-round selections, which include Jason Hursh in 2013, Justin Campbell in 2022 and Carson Benge in 2024.

500 : Wins for Holliday as OSU’s coach, making him the second-winningest coach in program history, behind only Ward.

Josh watched the program's success unfold firsthand.

"When we came here, Josh was just a baby, but he kind of grew up in our atmosphere," Tom said. "Baseball was his life."

When Tom was on recruiting trips, Ward babysat Josh. As Josh grew older and matured, those nights quickly evolved into lengthy conversations about baseball — strategy, ballpark specifics and professional favorites between the two.

Eventually, Josh became a recurring presence in OSU's dugout.

He grew close with program greats such as Robin Ventura and Pete Incaviglia, taking batting practice from Tom before games and trying to emulate their swinging mechanics and hitting tendencies.

"I wanted to learn how to bat left-handed because Robin Ventura batted left-handed," Josh said. "Before almost every game, I'd try to incorporate elements of his game and those of the other players into my own. And looking back on that, those were some of the best memories of my life."

As the program took shape in Stillwater, so did Josh. What began as his father's leap into uncharted waters quickly became the foundation of his own identity.

Allie P Reynolds Stadium wasn't just where Tom worked, it was where Josh spent the days of his youth. Where he learned the sport inside and out, and where OSU became inseparable from him.

"Josh was raised in Stillwater and he was raised on the field," Ward said. "Every day he was part of Oklahoma State baseball. So, you talk about someone who has lived and bled Oklahoma State, Josh Holliday has lived Oklahoma State from the day he was born."

'He's gonna be a head coach'

When Vanderbilt's recruiting coordinator position became vacant, one name was recurrent in recommendations from other coaches.

Josh Holliday.

Corbin — now in his 24th season as Vanderbilt's head coach — had recruited Josh out of high school as an assistant at Clemson. Corbin joked that Josh's playing career only validated his bitterness toward not "winning that recruiting battle with Oklahoma State."

At that time, Josh had become a hot commodity within the assistant coaching realm.

Vanderbilt was in need of a new assistant. Corbin had received word Josh wanted to advance in the coaching ranks. It was an ideal fit, in Corbin's mind.

"I knew that was a pure baseball mind," Corbin told The Stillwegian. "I just felt like he was always very inquisitive, very curious and open to learning, and he always loved to talk about baseball."

📺 Watch Corbin and Holliday at Vanderbilt demonstrate flyball drills

So, Corbin contacted then Arizona State head coach Pat Murphy, requesting to interview Josh for the vacant position. When Murphy granted his wish, Corbin moved quickly.

The interview came within weeks. And upon that moment, Corbin garnered a striking intuition.

"I told my wife Maggie early on, 'He's gonna be head coach," Corbin said. "I don't know how long he's gonna be here, but he'll be a head coach one day.

"If Oklahoma State ever became an opportunity, that would be the next coach."

The poise, attention to detail and knowledge of the game all stuck out to Corbin, he said. But above all else, Josh's curiosity and willingness to learn was the kill shot in the interview.

And little did Corbin know, his intuition would eventually become a reality.

Josh spent three seasons (2010-12) as an assistant under Corbin, and the results were apparent the moment of his hiring. Wins came in bunches, records were broken and the program reached new heights, reaching its current status as a college baseball titan.

"He was the first one that I've ever heard teach our kids split-rhythm hitting," Corbin said. "I mean that in terms of being able to hit the fastball, but also being able to hit a decelerated ball, too.

"He just thinks about the game so much differently than anyone else I know. And his way of thinking really resonated with our players."

Corbin called Josh's time at Vanderbilt three of his favorite seasons in his more-than-two-decade stint.

"Every time I talked to Josh, he's got a question about baseball where he wants to know an answer, but he also wants to know what you're thinking." Corbin said. "I think that's most important.

"I truly feel like you could put him in any sport, and he'd be a successful coach, because he's such a good teacher."

In that moment, Corbin said, he not only saw a rising star — he saw a future coach.

That carried over into the 2011 campaign. Vanderbilt matched a program record 54 wins and appeared in the College World Series for the first time under Corbin, who credited the program's success that season to Josh's coaching philosophies.

Eventually, the head coaching position at OSU opened. Corbin didn't hesitate to recommend Josh to then athletic director Mike Holder.

Josh built OSU into its current status — perennial Big 12 contender and a common feature in the Field of 64. Corbin guided Vanderbilt to four additional College World Series appearances, two national championships and six SEC titles.

For all the insight Corbin offered Josh, the impact ran deeper than mechanics or philosophy. It was in those unstructured moments where Josh found a model for the caliber of coach he wanted to become. Long after his time in Nashville ended, Corbin's influence remained tethered to Josh, woven into the way he thinks, leads and coaches.

"He's my Nick Saban," Josh said. "...The lessons I learned (at Vanderbilt) were immeasurable. But coach Corbin taught me so, so much, and I'll never forget my time there. Those were some of the best years of my time as a coach."

'He's a Cowboy through and through'

Steve Sabins spent one season at OSU in 2009 under former coach Frank Anderson, so he wasn't a stranger to Stillwater or Cowboy baseball.

Anderson hired him on staff as a graduate assistant for the 2012 season. But after Anderson's firing that offseason, his future in Stillwater appeared bleak, and the trajectory of his coaching career even bleaker.

Sabins, a native of Austin, Texas, often trained back home during the offseason. Such training sessions carried over into his post-playing career, where he often encountered former Major League Baseball star Matt Holliday — Josh's brother. The two swiftly grew a rapport and became training partners.

Shortly after Josh's hiring ahead of the 2013 season, Matt called Josh with a pressing opinion.

"Matt called Josh and told him, 'Hey, this guy is not a complete jerk, you should keep him on staff,'" Sabins, now in his second season as West Virginia's head coach, told The Stillwegian. "I didn't care about the message or how it came across, I just wanted to stay in Stillwater."

So, Josh kept Sabins on staff as a graduate assistant. But after Sabins finished his graduate degree, another obstacle came about.

Josh wanted to keep Sabins on staff, but the optics behind doing so made such a decision appear far-fetched.

So, the two spent days on end conversing and brainstorming ways to keep Sabins in Stillwater. Through each discussion, Sabins said he noticed the passion and dedication Josh had. Not only toward the program, but toward his staff members.

Eventually an agreement was made.

"He basically asked me to come up with a job title to make it work," Sabins said.

Director of player development.

There, Sabins managed OSU's video analysis program and scouted both game and practice footage. He provided feedback to hitters, infielders, and pitchers, all while preparing scouting reports for upcoming opponents.

OSU graduate assistant Roland Fanning (left) and head coach Josh Holliday direct players from the dugout during a game against Kansas on Saturday, April 19, 2014, at Allie P. Reynolds Stadium in Stillwater. Fanning later parlayed his time on Holliday's staff into a head coaching position at Austin Peay. – Photo Courtesy OSU Athletics

Roland Fanning spent two seasons as a graduate assistant at OSU from 2013-14. His career took him elsewhere afterward. First, as the recruiting coordinator at Little Rock. Shortly after at Kentucky.

But fate worked extra innings bringing him back to Stillwater. This time, with the same position Sabins once held. Three seasons later, Fanning accepted the head coaching position with Austin Peay.

"I came in thinking it was gonna be a one-year stint and it turned into three of the best years of my life," Fanning, now in his fourth season at Austin Peay, told The Stillwegian. "I got to show up every day, serve the program and do what I love. Josh gave me a lot of freedom and that played a big part in getting me to where I am right now."

Both Sabins and Fanning witnessed Josh's blueprint for the program take place. They were part of the program's Big 12 regular season championship in 2014. They witnessed blueprints and groundbreaking for O'Brate Stadium unfold, which eventually opened February 2021.

OSU is one of five programs to appear in a regional each season since Josh took over. The others? Vanderbilt, Louisiana State, Florida, and Dallas Baptist. The first three, perennial SEC juggernauts. The latter, a mid-major powerhouse that emulates a Power Four program in every fashion.

Beyond that 12-year regional streak — which excludes the COVID-19-shortened 2020 season — OSU has claimed three conference tournament championships, two regular-season titles, three super regionals, and made a College World Series appearance in 2016.

OSU head coach Josh Holliday signals from the dugout during the Cowboys' appearance in the 2016 College World Series against Arizona on June 20, 2016, at TD Ameritrade Park in Omaha, Neb. It was OSU's first College World Series appearance in 17 years. – Photo by Bruce Waterfield/OSU Athletics

Both witnessed most of the program's tail end success from afar. Yet, both held appreciation toward it, acknowledging their roots while staying true to their jobs in the present.

But most notably, both attribute their time working under Josh as vital chapters to their coaching tenures.

"Josh is one of the greatest mentors to me in the coaching profession," Sabins said. "He truly has the best interest of his players and coaching staff in mind and he goes out of his way to make things happen for them. And because of that, I think, his players play harder for him. So, I don't think I would be where I am right now without him."

When asked what came to mind when reflecting on their time with Josh, one word was recurrent between the two.

"Consistency," Fanning said. "He's a guy that's been ultra consistent. He's never missed a regional in the modern era, which is unheard of and I think is something that people kind of walk by sometimes. I know the history of Oklahoma State baseball is rich in tradition with conference championships, College World Series appearances and all that, and he's right up there with the greats.

"The Holliday name — that name holds a lot of value in Stillwater. But Josh, he's a Cowboy through and through."

The milestone moment

"What are some of your best memories as the head coach of Oklahoma State?"

Rather than sparking celebration from Josh, the question from O'Colly reporter Weston Wertzberger, drew reflection. Humility instead of euphoria. Meekness rather than jubilee.

Moments prior, OSU had bested Wichita State, securing Josh's 500th win at the helm. But his tone emulated a man embracing the past as opposed to one who had just experienced a monumental milestone.

OSU players douse head coach Josh Holliday with a Gatorade bath following a 14-4 run-rule victory over Wichita State on Tuesday, April 21, 2026, at O'Brate Stadium in Stillwater, giving Holliday his 500th career win as the Cowboys' head coach. – Photo by Bruce Waterfield/OSU Athletics

Josh glanced toward the walls inside the O'Brate Stadium team meeting room, analyzing every inch. Both sides are adorned with photos of monumental moments in program history — most transpiring during his tenure.

It's a unique yet quaint design, beautifying one of the team's commonly-used rooms. For Josh, it commemorates the rich history of OSU baseball and the plethora of talent that has come through it. All while serving as a memorandum of what is expected.

His favorite memories? The moments shared with coaches and players who have been part of his 14-year journey.

"There's a few of them on the wall there," he said with a smile that illustrated every bit of his emotional state. And he highlighted a handful.

The 2016 team's final out on the road against South Carolina in super regionals, clinching the program's first College World Series appearance in 17 years. The 2017 team dog-piling in front of the pitcher's mound after winning the Big 12 Tournament Championship, salvaging the team's postseason hopes and becoming the first 8-seed in conference history to attain that feat. Trevor Boone's ninth-inning go-ahead, three-run home run against Nebraska in regional play in 2019.

Oklahoma State players dog-pile on the pitcher's mound after defeating Texas 6-5 to claim the Phillips 66 Big 12 Baseball Championship on Sunday, May 28, 2017, at Chickasaw Bricktown Ballpark in Oklahoma City. The victory was the program's first Big 12 Tournament title under head coach Josh Holliday. – Photo by Bruce Waterfield/OSU Athletics

All of it, Josh noted, serves as a self-reminder for why he coaches. Each moment, a snapshot of realized purpose, and a testament to the standard he's spent a lifetime chasing.

So, when asked a second time of his favorite memories as the skipper of his alma mater, Josh deflected all notoriety toward his players — both past and current.

"I think this place is in a much better spot right now than when I got here — we're fortunate to have a beautiful home to play baseball in now," Josh said. "I'm thankful for all of the awesome kids that chose to come here and be part of this. They're really the story. I'm 100% not.

"When I played here, I was part of the story, because back then I was one of the kids suiting up and putting it up every day for OSU. As an adult, it's just been a chance to come back and serve a place I love."

It hasn't been smooth sailing for Josh since his hiring. Yet, the consistency the program has endured since his return to Stillwater puts OSU in rare company.

Josh acknowledged the standard at OSU is immense, and such a job isn't for the faint of heart.

The 2026 season has been a cruel mistress in many ways. A once promising start, hampered by untimely injuries to key pitchers and lineup members. Heading into a pivotal three-game series at Texas Tech, which begins Friday at 1 p.m. at Rip Griffin Park in Lubbock, Texas. The Cowboys (25-16, 8-10 Big 12) hold a prime opportunity to ignite a late-season surge and push toward extinguishing that aforementioned Omaha drought.

OSU head coach Josh Holliday watches from the dugout steps during a 2016 Bedlam series game against Oklahoma. The image captures the intensity Holliday brings to every at-bat, a trademark his players and former staff have noted throughout his 14-year tenure. – Photo Courtesy OSU Athletics

Yet, through the success, Josh has maintained one recurrent outlook on his tenure.

"It's been a lot of fun, it's been a lot of work, it's been a lot of time, and it's been everything that is good about what you do in life, all rolled together in one," Josh said. "...What has it taught me? Well, I think to answer that, you'd have to just stop for a minute and take a deep breath, right?

"Staying in the moment. I think that's what it's taught me — to stay in the moment."

Josh isn't just a steward of OSU — he's a product of it. The program that once took college baseball by storm before during his adolescence is now the one he directs. His outlook hasn't been altered in any way. Only his place within it has.

Much like Tom's November afternoon in the press box, where the program's past and present shared the same space, Josh's task is simple — preserving what was built while ensuring OSU baseball never drifts far from where it began.

Since his return to Stillwater, he's "fought like crazy" to protect it. Still leering over the dugout edge every at-bat, still shouting unorthodox words of encouragement to hitters and still sporting OSU colors as if they're part of his life.

And in many ways, they are.

"We had to build something back then," Tom said. "Josh is trying to maintain it. As hard as he works, it parallels the effort we gave when we got here ... he's at the point where no matter what you say or no matter what you give him, he's gonna make it work.

"There's nobody better for that job at Oklahoma State than Josh Holliday. That I can tell you for certain."

#OkState coach Josh Holliday speaks on attaining win No. 500 as head coach. pic.twitter.com/O9uwwL7suL

— Daniel Allen (@bydanielallen25) April 22, 2026