DENVER -- Twenty years ago, an 18-year-old, curly-haired Matthew Holliday, fresh out of Stillwater (Okla.) High School, embarked for Rookie-level ball in Tucson, Ariz.
On Saturday, Holliday -- with less hair, but with his wife, Leslee, and four children -- headed to Grand Junction, once more for Rookie ball.
Holliday, a seven-time All-Star who did not sign with a team during the offseason and spent the season as a radio host, agreed to a Minor League contract with the Rockies in hopes of helping his old club during the stretch run. He will have a physical Saturday, work out with Grand Junction for a few days, then join Triple-A Albuquerque.
If all goes well, he can rejoin the club he played for from 2004-08 as a right-handed option when the roster expands to 40 in September, much the way Jason Giambi did when he was signed after being released by the Athletics in 2009. Giambi hit .292 with two homers and 11 RBIs while helping the Rockies to the playoffs.
"I always enjoyed my time in Colorado," Holliday said. "Even during the 10 years that I've been gone, I always kept in touch with a lot of the people and players. I've always had an affection for the organization. I've always thought if I had the chance to go back, it would be real special."
With the physical pending, the Rockies have not announced the move officially.
Holliday played last season with the Yankees and batted .231 with 19 home runs and 64 RBIs in 105 games as a first baseman/designated hitter. Holliday dealt with back problems throughout the season and appeared in just one postseason game.
Holliday has four children who play baseball -- sons Jackson (14 years old), Ethan (11), and Reed (5), and daughter, Gracyn (8). Living in Jupiter, Fla., Holliday threw batting practice, then found time to hit, throw and field on his own. Not long ago, Holliday received a call from Colorado general manager Jeff Bridich that "got the juices flowing."
Holliday, who said his body has healed, began working out in earnest and came to the Minor League agreement on Saturday.
"I had a couple of people call during the winter, but I thought that there were just a few teams I'd want to play for if the opportunity came along," he said. "I am good to go."
Holliday said he has been working at first base and in the outfield.
The 38-year-old has a .299 career average with 314 home runs and 1,217 RBIs during his 14 seasons in the Majors. His best year was 2007, when he led the National League in batting (.340), hits (216), doubles (50) and RBIs (137). Holliday was nosed out of the NL MVP Award by the Phillies' Jimmy Rollins.
Should Holliday make it back to the Majors with the Rockies, it will be an interesting meeting with manager Bud Black.
Holliday scored the winning run in the bottom of the 13th inning in Colorado's epic 9-8 victory over the Padres in Game 163 of the 2007 season that sent the Rockies to the postseason as the National League Wild Card. Black was managing the Padres at the time, and San Diego contends that Holliday did not touch home plate. But in those days before replay challenges, there was no way to reverse the ruling. Holliday was knocked loopy in the collision with Padres catcher Michael Barrett.

Colorado swept its way to the World Series, where the Rockies were swept by the Red Sox. En route to the Fall Classic that year, Holliday was the Most Valuable Player of the NL Championship Series against the D-backs.
Holliday said he has spoken to Black over the years, but they've never broached the subject.
"If I get to the Rockies, I'm sure we'll sit down," Holliday said, chuckling.
Believing that they could not sign him when free agency hit, the Rockies traded Holliday to the Athletics for outfielder Carlos Gonzalez, relief pitcher Huston Street and starting pitcher Greg Smith on Nov. 10, 2008. Gonzalez became a three-time All-Star for Colorado, while Street appeared in 170 games over three seasons with the club.
After the blockbuster trade with Oakland, Gonzalez assumed Holliday's No. 5 with the Rockies and has admired Holliday.
"That'd be crazy to be on the same team. … He can still play, man," Gonzalez said.  
Holliday played just 93 games with the Athletics in 2009 before he was traded to St. Louis, where he played eight seasons and became a four-time All-Star. Holliday won the World Series with the Cardinals in 2011.
The pending signing is a move similar to a flyer the Rockies took last year, when they signed former Phillies star first baseman and 2006 NL MVP Ryan Howard. Howard hit .192 with three homers and eight RBIs for Triple-A Albuquerque but was never called to the Majors.