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Holliday began working with former A's and Cardinals first baseman Mark McGwire as a personal hitting coach during the 2008–09 off-season, who became the Cardinals' official hitting coach the following off-season. Those two neutral parties spent a significant chunk of the celebration and post-game discussing how it didn’t look like Holliday even touched the plate. Matt Holliday scored the winning run in Game 163 of the Colorado Rockies’ 2007, but only because the umpire, Tim McClelland, blew the call. Back in 2007, where the HD television quality isn’t quite as wonderful as you remember it being, MLB wasn’t using video review. So, what the umpire said went as the call on the field, and McClelland eventually got to calling Matt Holliday safe for his slide into home plate in extra innings. Scored the winning run in Game 163 of the Colorado Rockies’ 2007 season.
He played 72 games on the season after undergoing elbow surgery in July ended his season. The contract to which Holliday and the Cardinals agreed before the 2010 season was widely viewed as a great success. Over its first five seasons, he averaged 147 games per season, .295 batting average, .383 OBP and .496 SLG for a 141 OPS+; his counting stats average included 24 home runs, 93 RBI, and 92 runs scored. Since being acquired from Oakland, Holliday ranked fifth in MLB in RBI, doubles, and runs scored, ninth in extra-base hits, and 14th in OPS. After returning from the DL, Holliday's first home run was a grand slam on July 21 against Carlos Rodon of the Chicago White Sox in an 8–5 win, his sixth career grand slam. He reinjured the right quadriceps on July 30, prompting the club to retract him to the DL.
Survey of free agent contract signed in 2010
The Rockies posted the largest comeback in team history in a nine-run deficit on July 4 against the Florida Marlins. After the Marlins led 13–4, Holliday provided two home runs, including a grand slam to reduce the Marlins' lead to 17–16 in an eventual 18–17 win. On July 6, Holliday was named a reserve outfielder for National League in the All-Star Game for the third consecutive year. He replaced Chicago Cubs outfielder Alfonso Soriano, who did not play due to injury, as the starter in right field, and hit a solo home run in the top of the fifth inning. For the month of July, he batted .370 with eight home runs and 24 RBI, .660 slugging percentage and 24 runs scored in 27 games. Holliday's August totals included 11 stolen bases and 30 runs scored in 28 games, six home runs, nine doubles and a .392 on-base percentage.

One opponent with long-time ties to the Hollidays is former Boston Red Sox manager John Farrell. Farrell pitched for Tom Holliday at OSU, helping propel them to four College World Series appearances. When Matt and Josh were still toddlers, Farrell often babysat them when their parents went out. Years later, when Matt Holliday was a member of the Rockies team that played the Red Sox in the 2007 World Series, Farrell was the Red Sox pitching coach.
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The Cardinals reactivated him on September 15 after missing 41 games. Holliday played 73 games and finished the season with a .279 batting average, .394 on-base percentage, .410 slugging percentage, .804 OPS, four home runs and 35 RBI in 277 plate appearances. Batting second, Holliday homered in four consecutive games from June 18 to 22. In a weekend series against Oakland from June 18 to 20, he drove in eight of the Cardinals' 12 runs. He was named the National League Player of the Week for June 20, batting .435 with four home runs and eight RBI. Selected to the All-Star Game on July 4 as a reserve player, he also participated in the Home Run Derby.

Six years after that, as a member of the St. Louis Cardinals, Holliday again played against Farrell. In both Series, however, Farrell's teams were victorious over Holliday's. With intense off-season physical training regimens, Holliday plays squash and likes to incorporate an NFL approach.
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Colorado was gifted a run it probably didn't deserve, but really, it was making up for another run they'd been wrongly denied -- and which would've changed the entire complexion of the game. The second is from down the left-field line -- it certainly seems to give the impression that Barrett blocked Holliday from reaching the plate, but it doesn't allow us to see what went on behind Barrett's left foot, so it's still inconclusive. That's where it remained until the 13th, when Scott Hairston launched a two-run homer to give the Padres the lead. San Diego was at the doorstep yet again, three outs away from the postseason with future Hall of Famer Trevor Hoffman making his way to the mound. But baseball has been around a long time, and in some cases, it can be hard to tell whether those stories are too good to be true. Which is why MLB Mythbusters is here to help -- we'll be diving into some of the game's greatest legends, trying to separate fact from fiction.

Continuing to evolve as a hitter, Holliday started the 2007 season as in the Rockies' lineup as the number five hitter, but changed to the third slot for the final five months of the season. He fashioned a new career-high 14-game hitting streak that spanned from April 17 to May 1. His two outfield assists on April 21 against San Diego in the sixth inning tied a club record for outfield assists in one inning.
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He played 32 games and assembled 40 hits in 117 at bats for a .342 batting average, collected four doubles, a triple, five home runs and 23 runs batted in ; his home run total placed third in the league. He played 1999 for the Asheville Tourists, batting .264 with 16 home runs and 76 runs scored. With the bases loaded, he was 3-for-9 with one grand slam and 11 RBI. At third base, Holliday turned in an .871 fielding percentage and 57 putouts.
He has trained with teammates, such as Freese, and pitcher Trevor Rosenthal, in activities such as "sled pushing, tire flipping and some fireman carries", and each player taking turns carrying each other for about 20 metres. Scott Boras has represented Holliday as his agent since he turned professional. Fangraphs' Wins Above Replacement formula rated Holliday's production equivalent to nearly $110 million in value while actually being paid just $84 million. In that span, he ranked 11th in all MLB, and fifth among outfielders, with 23.8 WAR.
Holliday totaled 125 games and improved in nearly all offensive categories from his rookie year, including 147 hits, 19 home runs, 87 RBI, 68 runs, 14 stolen bases, 242 total bases, 505 slugging percentage and .361 on-base percentage. The club picked up his option for 2006, which was worth $500,000 ($693,729.8 today), or about $100,000 ($138,746 today) more than the average for a player with equivalent service time. The Arizona Fall League announced on July 20 that Holliday, along with fellow outfielder Carl Crawford, were selected to their Hall of Fame. On September 12, his 467 feet home run against the Rockies was the longest home of the season at Busch Stadium and the second-longest in the stadium's history, just after the one he had hit two years earlier against the Cubs. He finished the season with a .272 average, 20 home runs, 90 RBI , 37 doubles, 83 runs scored, 74 BB , 247 times on base , .370 on-base percentage and .443 slugging percentage.

The Rockies also offered a four-year, $72 million extension, with a club option for a fifth year at $12 million. The team viewed the contract extension with the two years covering arbitration as a singular deal worth approximately $107 million. In contrast, Holliday and his agent, Scott Boras, regarded the extension as an $84-million free agent contract undervalued compared to similar players. At Stillwater High School, Holliday played both baseball and football.
Because of his hitting abilities and strength, he has sometimes been called the "Stillwater Stinger". With Coors Field absolutely losing its mind, Hoffman intentionally walked Todd Helton, putting runners on the corners with no one out for infielder Jamey Carroll. Carroll jumped on the first pitch he saw, hitting a line drive directly at Giles in right. Holliday -- at 6-foot-4, 240 pounds, not exactly the swiftest guy on the bases -- tagged up, looking to come home with the winning run and send the Rockies to the NLDS for the first time since 1995. That’s in reference to the controversial final play of the 2007 NL Wild-Card Tiebreaker Game. Holliday was ruled safe at home on Jamey Carroll’s walk-off sacrifice fly, but the debate has raged on for over a decade over whether Holliday ever really touched home plate.
He singled in Jon Jay to drive in the 1,000th run of his career on June 17 at Busch Stadium against Washington, the 277th player in MLB history to do so. While batting against Dan Haren of the Dodgers on July 19, Holliday hit his 400th career double and hit a 435 feet home run for his 1,000th run scored. The Rockies assigned Holliday to their Triple-A affiliate, the Colorado Springs Sky Sox, at the outset of the 2004 season, intending for him to spend much of the season there. Injuries to outfielders Preston Wilson and Larry Walker expedited his progress to the Major Leagues after just six games with Colorado Springs.
The A's defeated the Minnesota Twins 14–13 on July 20 following a 10-run comeback, the largest in team history. Holliday contributed two home runs and six RBI, including a seventh-inning grand slam that tied the score at 13. This game marked the second time in his career in which he hit a grand slam plus another home run in his team's record-breaking comeback.
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