There, the Holliday boys learned about the fundamentals of the sport, voluntarily trained and practiced, and watched future major leaguers such as Robin Ventura play and develop.

[7] Former Dallas Cowboys head coach Jimmy Johnson reportedly once forecasted to Tom Holliday that his son "couldn't miss" as an NFL prospect.

[10] His older brother, Josh, is currently the head baseball coach at OSU, and a former minor league player in the Toronto Blue Jays organization.

He made his major league debut in left field on April 16[22] at Busch Memorial Stadium against one of his future teams, the St. Louis Cardinals.

[23] Two days after his debut, Holliday recorded his first career hit, a single, and then, RBI against the Cardinals' Woody Williams, doubling in Kit Pellow.

Five days later, he, Jeromy Burnitz, and Charles Johnson collaborated for back-to-back-to-back home runs against the Florida Marlins, the sixth such occasion in franchise history.

His first MLB grand slam came against the Tampa Bay Devil Rays on June 12, immediately tying a game in which the Rockies had faced a 5–1 deficit.

[27] He earned his first NL Player of the Week award for July 25 to 31, after batting .444 with three home runs, eight RBI, an .852 slugging percentage and a league-leading 12 hits and 23 total bases.

[40] In the April 29 contest against the Braves, Holliday hit his first career walk-off home run in the bottom of the 11th off Bob Wickman to provide a 9–7 victory.

[55] Holliday scored the winning run on Jamey Carroll's sacrifice fly in a bloody collision with catcher Michael Barrett, although controversy arose as to whether he touched home plate.

[83][84] He replaced Chicago Cubs outfielder Alfonso Soriano, who did not play due to injury, as the starter in right field,[85] and hit a solo home run in the top of the fifth inning.

He led the club with 28 stolen bases while posting a .409 on-base percentage, both career highs, and won his third consecutive Silver Slugger Award.

[88] Defensively, Holliday was first in ultimate zone rating (.900), fourth in fielding percentage (.991), fifth in total chances (252) and fifth in putouts (240) among all MLB left fielders.

[89] Unable to agree to an extension, the Rockies traded Holliday on November 12, 2008, to the Oakland Athletics for pitchers Huston Street and Greg Smith, and outfielder Carlos González.

[114] Los Angeles swept the best-of-five series, ending the Cardinals' season,[110] and the Game 2 error left Holliday with a reputation as a "goat.

[131] The St. Louis chapter of the Baseball Writers' Association of America recognized his charitable work and role as a team leader with the Darryl Kile Good Guy Award.

[151] During the NLCS against the Giants in Game 2, he slid into second baseman Marco Scutaro during a routine ground ball double play and ended up on top of him.

[158] He left the July 11 game against the Cubs early because of a tightened right hamstring sustained while running to first base,[159] prompting the Cardinals to place him on the DL.

Holliday collected six hits in 24 at bats with one double, one triple and two home runs for a .625 slugging percentage; however, the Red Sox claimed the title in six games.

[187] On June 8, Holliday suffered a right quadriceps strain while diving for a fly ball off the bat of the Rockies' Carlos González, and the Cardinals placed him on the 15-day DL.

He continued to reap considerable vote totals in spite of missing a month, and eventually was chosen a starting outfielder for the first time in his career.

Having been informed in the final days of the 2016 season that the Cardinals would not pick up the option for 2017 worth $17 million, he was activated from the DL — although his thumb was still fractured — in time for the September 30 game against Pittsburgh.

Because he produced the third-highest exit velocity at 94.7 miles per hour (152.4 km/h) of all hitters with at least 100 batted balls in 2016, he concluded that to "have my misses be more in the air than on the ground, my numbers could really get back toward where they have been my whole career.

"[206] After becoming a free agent for the second time in his career, on December 7, 2016, Holliday signed a one-year contract with the New York Yankees worth $13 million,[207] to become their primary designated hitter (DH).

[213] On April 28, Holliday hit a walk-off three-run home run off Jayson Aquino, which capped a comeback after trailing 1−9, and helped a 14−11 win over the Orioles.

They met on a blind date in 1999 in Stillwater during the baseball offseason when Matt had returned home from his first professional season following his selection by the Rockies in the MLB draft and Leslee was an undergraduate at OSU−Stillwater.

[246] In the 2014−15 offseason, Holliday and his family moved to South Florida, allowing him to stay in optimal shape year-round, and his sons to continue to play sports in winter months.

[250][251] Known primarily as a reserved figure, Holliday has played for years in the shadows of such franchise icons as Todd Helton and Albert Pujols, which accommodated his demeanor well.

However, he has emerged as a veteran presence for the Cardinals willing to assist and entertain younger players and top prospects as they attempt to adjust to a lifestyle of playing baseball.

In January 2012, he invited Matt Adams, Ryan Jackson, Charlie Tilson and Kolten Wong for a weeklong stay in St. Louis at the tony Frontenac Hotel.