JAWS and the 2024 Hall of Fame Ballot: Matt Holliday

The following article is part of Jay Jaffe’s ongoing look at the candidates on the BBWAA 2024 Hall of Fame ballot. For a detailed introduction to this year’s ballot, and other candidates in the series, use the tool above; an introduction to JAWS can be found here. For a tentative schedule, see here. All WAR figures refer to the Baseball-Reference version unless otherwise indicated.

At his listed size of 6-foot-4, 240 pounds, Matt Holliday was built like a football player. He could easily have gone in that direction, having excelled as a quarterback in high school and received scholarship offers from big-time college programs. Holliday came from a baseball-rich family, however, and his heart was on the diamond, so he chose to follow in the footsteps of his father and older brother, both of whom played professionally. He surpassed both not just by reaching the majors but by becoming a star, making seven All-Star teams in a 15-year career spent with the Rockies, A’s, Cardinals, and Yankees. He won a Coors Field-aided batting title as well as NLCS MVP honors while leading the Rockies to their only World Series berth in 2007. Winning seemed to follow Holliday, or perhaps it was the other way around; nine times in those 15 seasons his teams made the playoffs, with three trips to the World Series including a championship in 2011.

Matthew Thomas Holliday was born on January 15, 1980 in Stillwater, Oklahoma. His father, Tom Holliday, spent a year in the Pirates’ organization before pursuing coaching at the collegiate level. From 1978–96, he served as Oklahoma State University’s pitching coach and recruiting coordinator, then took over as head coach from ’97–2003. His oldest son, Josh Holliday (b. 1976), starred at Stillwater High School ahead of Matt; the two played on the same team in 1995. Josh was drafted by the Twins in the 14th round in 1995 but instead chose to go to Oklahoma State, where he played for his father and helped the team to the College World Series in ’96 and ’99. Drafted again by the Blue Jays in the ninth round in 1999, he spent two seasons playing professionally before going the college coaching route; he took over as Oklahoma State’s head coach in 2013, and still holds the job.

As kids, the Holliday boys got to watch OSU stars such as Robin Ventura and Pete Incaviglia set NCAA records. Matt starred in baseball, football, and basketball as a youth; his father coached him in the last of those sports during the baseball offseason. Big for his age even before growing to his adult size, he was always at an advantage when playing with friends: “[T]hey would rig the rules to make it fair for everybody,” wrote the New York Times‘ Tyler Kepner in 2007. “In football, Matt had to be quarterback for both teams. In a home run derby, he had to hit three homers to get credit for one.”

At Stillwater High, Holliday earned All-American honors and his region’s Gatorade Player of the Year in both football (as a QB, he threw for over 6,000 yards with 68 touchdowns and broke several state records set by Troy Aikman) and baseball. He was recruited as a QB by Notre Dame, Florida State, Tennessee, Miami and other top college programs. He signed a letter of intent to play both sports at Oklahoma State, but baseball had a hold on him. Scouts viewed him as a five-tool player but something of a wild card since football was still in the picture. His uncle, Dave Holliday, a scout for the Rockies, recommended him, and the team drafted him in the seventh round in 1998. He signed for a $842,500 bonus (or thereabouts, as even within Baseball America, sources differ). The bonus — more than some late first-rounders and most second-rounders — set a record for a player taken so late in the draft. As part of the deal, Holliday could return to college to pursue football after three seasons.

Holliday was drafted as a third baseman, and began his pro career at the hot corner, hitting .342/.413/.521 in 32 games for the Rockies’ Arizona League affiliate in 1998. High error totals and a failure to fully realize his game power kept him off of Baseball America Top 100 Prospects lists. He hit .264/.350/.435 with 16 homers while making 37 errors at A-level Asheville in 1999, then slipped to .274/.335/.389 with seven homers and 32 errors at High-A Salem the next year.

In 2001, the Rockies moved Holliday to left field while having him repeat at Salem. He hit .275/.358/.475 with 11 homers in 72 games before his season ended due to Tommy John surgery on his right (throwing) elbow. While he was recovering, the Rockies signed him to a six-year deal that guaranteed him a minimum of $700,000 (more if he was in the majors), added him to the 40-man roster, and closed the door on football. He spent 2002 and ’03 at Double-A, slugging in the .390s with a total of 22 homers, but a strong showing in the Arizona Fall League after the latter season kept him on the radar nonetheless.

The Rockies assigned the 24-year-old Holliday to Triple-A Colorado Springs to start the 2004 season, but he played just six games there before getting called up when Preston Wilson landed on what was then the disabled list, with Larry Walker already there due to a groin injury that would keep him out until June 22. Holliday debuted on April 16, 2004, going 0-for-4 against the Cardinals’ Matt Morris and Steve Kline in St. Louis (a significant detail in his career, he later said). After another 0-fer, he went 3-for-3 with a double off Woody Williams on April 18. On April 22, in his third game at Coors Field, he hit an RBI double and two-run homer off the Dodgers’ Jose Lima. He hit .317/.367/.594 through his first 29 games, but he cooled off before a left elbow sprain ended his season in mid-September, finishing at .290/.349/.488 with 14 homers. In that high-offense environment, such production equated to just a 103 OPS+, and with subpar defense (-9 DRS), just 0.5 WAR.

Holliday quickly improved, hitting .307/.361/.505 (114 OPS+) with 19 homers, 14 steals, and 2.8 WAR in 2005 despite missing nearly six weeks due to a broken right pinky, suffered while making a headfirst dive. He broke out in 2006, hitting 34 homers – one more than he’d hit in his first two seasons combined — to go with a .326/.387/.586 (137 OPS+) line. He made his first All-Star team, and even received down-ballot mention in the MVP voting. In 2007, he topped just about all of that, hitting .340/.405/.607 while leading the league in batting average, hits (216), doubles (50), RBI (137), and total bases (.386); his slugging percentage ranked third, his 151 OPS+ fourth, his 6.0 WAR seventh.

The Rockies had gone six years since their last finish at .500 or better, and 12 since their lone playoff appearance. With 14 games to play, they were 76-72, 6.5 games out of first place and 4.5 back in the Wild Card race. With Holliday hitting an unreal .429/.525/.816 with five homers and 15 RBI in 59 plate appearances, they went 13-1 to tie the Padres for the Wild Card spot at 89-73. The two teams met for a Game 163 playoff at Coors Field, a wild, 13-inning affair. Holliday walked and scored in the first inning as the Rockies built a 2-0 lead against Jake Peavy, but Adrián González gave the Padres a 4-3 lead with a third-inning grand slam off Josh Fogg. Holliday tied the game at 5-5 with an RBI single following a Troy Tulowitzki double to start the fifth. Through nine innings, the two teams were tied 6-6, but the Padres finally broke through with Scott Hairston‘s two-run homer in the top of the 13th. Not to be outdone, the Rockies teed off on Padres closer Trevor Hoffman in the bottom of the 13th, with Kazuo Matsui and Tulowitzki hitting back-to-back doubles, and Holliday knotting the game with an RBI triple off the right field scoreboard, just over Brian Giles‘ head. Hoffman intentionally walked Todd Helton, but when Jamey Carroll hit a line drive to right field, Holliday tagged up. Giles’ throw beat him home; Holliday slid around Michael Barrett’s left foot, which was blocking the plate, but the catcher lost the ball. Umpire Tim McClelland hesitated for a few seconds before calling Holliday safe, though via replays, it appeared he had never touched home plate. There was no mechanism in place by which to review the call, and the Padres didn’t make much of an effort to get the umpires to confer, so the Rockies won.

Holliday and the Rockies kept rolling, sweeping the Phillies in the Division Series and the Diamondbacks in the NLCS, with the slugger homering twice in each series and earning MVP honors in the latter on the basis of a .333/.412/.733 performance. He homered in Game 3 of the World Series as well, but the Rockies were swept by the Red Sox.

After the season, Holliday finished a close second behind Jimmy Rollins in the NL MVP voting. He signed a two-year, $23 million extension in January 2008, then followed up with another All-Star campaign (.321/.409/.538, 138 OPS+, 25 HR, 5.9 WAR). The Rockies slipped to 74 wins, however, and with Holliday’s free agency just a year away, they decided to trade away their big bopper. On November 10, 2008, he was sent to the A’s in exchange for outfielder Carlos González and pitchers Greg Smith and Huston Street.

He didn’t stay long in the Bay Area. The A’s had gotten as far as the ALCS in 2006 but declined to 76 wins in ’07 and 75 wins in ’08. They were in the midst of charting a similar course in 2009 when they flipped Holliday to the Cardinals in exchange for a trio of players (pitcher Clayton Mortensen, outfielder Shane Peterson, and infielder Brett Wallace) who never panned out and who combined to play in just eight games for Oakland. Holliday, who had hit for a 120 OPS+ with 11 homers in 93 game for the A’s, hit for a 169 OPS+ (.353/.419/.604) with 13 homers in 63 games for the Cardinals, whom he helped win the NL Central.

Holliday went just 2-for-12 as the Cardinals were swept by the Dodgers in the Division Series. Though he homered off Clayton Kershaw in the second inning of Game 2, he dropped what would have been a game-ending fly ball off the bat of James Loney in the bottom of the ninth, and barely avoided getting hit in the groin. The pinch-runner for Loney came around to score the tying run, and the Dodgers scored the winning run five batters later via Mark Loretta’s single.

“I got caught. I can catch a ball hit right at me,” Holliday told reporters afterwards. “It went in the lights, and I couldn’t see the ball. Hit me in the stomach… I was just hoping it would hit my glove.”

Despite the gaffe, Holliday had such a positive experience in St. Louis that he re-signed with the team upon reaching free agency, agreeing to a seven-year, $120 million deal, which would stand as the largest in franchise history until Paul Goldschmidt inked a five-year, $130 million extension in 2019. Upon induction to the Cardinals’ Hall of Fame in 2022, Holliday said that making his major league debut in St. Louis while with the Rockies “began my love affair with dreaming of someday being a St. Louis Cardinal.”

Near the end of the 2009 season, as free agency approached, teammate Adam Wainwright told him, ‘You know, if you don’t sign back here, I’m going to peg you every time I face you the rest of your career.”

“I thought, ‘Well, you don’t throw that hard, so I’m not too worried about it,’” joked Holliday.

Secure in his new home, Holliday made the NL All-Star team in each of the next three seasons, hitting a combined .302/.385/.517 (146 OPS+) while averaging 26 homers and 4.6 WAR, with a high of 5.9 WAR in 2010 thanks to his 7 DRS; he would spend the rest of his career in the red. The Cardinals missed the playoffs in 2010 while going 86-76. Holliday was limited to 124 games in 2011 due to an appendectomy, a quad strain, and tendinitis in his right middle finger; he played just four games after September 13 and was a bystander as the team eked out a Wild Card berth with a win and a Braves loss on the final day of the season. He also entered the annals of bizarre baseball injuries when he left the team’s August 22 game after a moth flew into his right ear during a game and decided to stay there, much to the left fielder’s chagrin.

In the postseason, Holliday didn’t drive in a run in either the Cardinals’ Division Series win over the Phillies or their World Series win over the Rangers, but he hit .435/.500/.652 in their NLCS win over the Brewers. Unfortunately for him, he missed much of Game 6 of the World Series and all of Game 7. With the bases loaded in the sixth inning of Game 6, he was picked off of third base, and Adrián Beltré accidentally stepped on his right hand, injuring his pinky and straining his wrist. The Cardinals had to replace him on the roster but won the series nonetheless.

Holliday was less impactful in the 2012 postseason despite going 2-for-3 with an HBP and a solo homer in the Cardinals’ Wild Card win over the Braves. He hit a combined .224/.296/.306 overall as the team ultimately bowed to the Giants in the NLCS.

Holliday missed out on making the All-Star team in 2013 despite a .300/.389/.490 (142 OPS+) season, though his career-worst -14 DRS led to him finishing with just 2.6 WAR, his lowest total since his 0.5 WAR as a rookie. He did help the Cardinals to their first division title since 2009, and hit a lopsided .246/.268/.507 with four homers and 10 RBI in the postseason as the team made it back to the World Series. With the Cardinals down two games to one against the Pirates in the Division Series, his two-run sixth-inning homer off Charlie Morton provided all the offense the team needed in Game 4. He hit a big two-run homer off the Dodgers’ Ricky Nolasco in a 4-2 win in Game 4 of the NLCS, and broke a 2-2 tie with a decisive two-run double off the Red Sox’s Junichi Tazawa in the seventh inning of Game 3 of the World Series. The Cardinals won that game to pull ahead two games to one, but that turned out to be their final win of the season.

After another solid season (127 OPS+, 3.3 WAR) while helping the Cardinals to a division title in 2014, Holliday hit a huge go-ahead three-run homer off Pedro Báez – who had just relieved a faltering Kershaw — in the seventh inning of the Division Series opener. He went just 7-for-33 without an RBI in the Cardinals’ other eight postseason games; they were again ousted by the Giants in the NLCS. A recurrent quad strain limited Holliday to 73 games in 2015. He earned All-Star honors for the seventh and final time of his career on the strength of a .303/.417/.421 (130 OPS+) first half, but hit just .196/.305/.373 (84 OPS+) in 21 second-half games and went just 2-for-16 in a Division Series loss to the Cubs.

Unfortunately, he wouldn’t come close to playing a full season again. In the final guaranteed year of his contract, the 36-year-old Holliday hit .246/.322/.461 (107 OPS+) with 20 homers in 110 games, missing seven weeks after a fastball from the Cubs’ Mike Montgomery fractured his right thumb. Just before the Cardinals activated him, general manager John Mozeliak informed him that the team wouldn’t be picking up his $17 million option, and soon afterwards told the public as well. Holliday hit a pinch-homer off the Pirates’ Zach Phillips in his return on September 30, and collected an RBI single in the pinch off Juan Nicasio amid a game-tying rally the next day. In the season’s final game, manager Mike Matheny inserted him as a defensive replacement for a one-pitch cameo in the ninth inning, giving him the opportunity to receive a farewell ovation from the Busch Stadium crowd.

Holliday hit free agency and landed a one-year, $13 million deal to be the Yankees’ primary designated hitter. His time in pinstripes started out well enough. On May 3, he hit the 300th home run of his career, a three-run shot at Yankee Stadium off Marcus Stroman.

Holliday hit .262/.366/.511 with 15 homers before landing on the injured list with what was later diagnosed as the Epstein-Barr virus, which caused him fatigue and body aches. After missing 14 games, he hit just .174/.219/.292 the rest of the way while being sidelined an additional four weeks due to a lower back strain and finishing with a career-worst 95 OPS+. Unable to find a deal to his liking as a free agent, he sat out the first four months of 2018, but in late July agreed to a minor-league deal with the Rockies, who were en route to a Wild Card berth. He played one game with the team’s Rookie League affiliate and 15 more at Triple-A Albuquerque before joining the big club in late August. In the third game of his comeback, he hit a pinch-homer off the Cardinals’ John Gant to break a scoreless tie and spur a 9-1 win. He hit a respectable .283/.415/.434 in 65 PA, and played in all four of the team’s postseason games, going 2-for-8 with a double; the Rockies beat the Cubs in the NL Wild Card game but were swept by the Brewers.

After the season, Holliday returned to Stillwater, joining older brother Josh’s staff as a volunteer assistant coach for Oklahoma State, “responsible for the team’s offensive development and outfield play,” according to the OSU website. He’s still in that role after briefly accepting and then resigning from the job as the Cardinals’ bench coach last winter due to family reasons. As for that family, in July 2022, Jackson Holliday — the oldest of his four children — was chosen out of Stillwater High School with the first pick of the amateur draft by the Orioles. He placed ninth on our Top 100 Prospects List in the spring of 2023, and after rocketing through four levels this past season while hitting .323/442/.499 with 12 homers and 24 steals, the 20-year-old shortstop is currently the top-ranked prospect on The Board. Younger brother Ethan Holliday, who’s already 6-foot-4 like his father, is considered a potential top pick for the 2025 draft as well.

Holliday doesn’t have the numbers for Cooperstown. In the best stretch of his career, from 2007–12, he ranked eighth among all position players in WAR, that while ranking among his league’s top 10 just three times, and never higher than seventh. His -43 runs as a left fielder simply limited his value. But like Walker before him and Nolan Arenado after him, he showed that a very good hitter at Coors Field could be a very good hitter elsewhere, even while the home/road splits looked different (obviously, the Cardinals were never scared away):

Holliday ranks 36th among left fielders in JAWS (one spot above another Cardinals legend, Lou Brock, whose full impact I believe isn’t captured by WAR). He was a fitting choice for the Cardinals’ Hall of Fame, of course, and with his progeny poised to make an impact in the majors, his career will continue to be celebrated.