By the time he was drafted again in 2002, it was in the 13th round by the Tampa Bay Devil Rays. Harrington was drafted twice more: in 2003 by the Cincinnati Reds in the 24th round and finally by the New York Yankees in the 36th round in 2004.
Just a week ago, Harrington signed a minor league contract with the Cubs. He received no signing bonus and no guarantee that he'd make a minor league roster out of Spring Training next year.
Once armed with a high-90s fastball, Harrington's velocity dipped over the years, as did his stock. He had spent the past four seasons pitching for the Fort Worth Cats, an Independent League team.
Cubs Director of Player Development Oneri Fleita played a big role in the decision to sign Harrington.
"It wasn't that big of a deal," Fleita said. "We have sources, we have scouts, and some people who recommended him. They said they thought he lost a lot of weight over the course of this past season and picked up some velocity on his fastball. He worked really hard and deserved an opportunity to finally get signed by a professional team."
Harrington was first drafted out of Palmdale High School in California. Along the way, he switched agents and sued original agent Tommy Tanzer for "bad advice," which reportedly included Harrington rejecting a signing bonus of $4 million from the Rockies and a guaranteed September call-up by 2002.
Harrington partnered with popular agent Scott Boras following the 2000 draft and would turn down a $1.2 million signing bonus with the Padres after the '01 draft.
Cubs Scouting Director Tim Wilken remembered Harrington from his days in Toronto as the Blue Jays' head of scouting, but said he hasn't seen Harrington pitch since 2000.
"At that time, we had a pretty strict budget and we just weren't in the neighborhood," Wilken said. "He had a pretty good arm, but his command and control was somewhat questionable. From what I understand, he's quite a bit of a different pitcher now than what he was in high school."
Wilken did say the right-hander was high on Toronto's list at the time.
"I remember he had good velocity," said Wilken, who was named Cubs Scouting Director this past December. "I want to say he was a 93-97 (mph) guy at one time. I think he had a pretty good breaking ball that was more of a hard slurve. He had a strongly built frame and his delivery was OK.
"Seven years, and I just more or less turned the page."
All the same, the Cubs seem excited to give Harrington a chance to try and rediscover the magic that once made him worthy of high-round consieration.
"Some people mature a little later than others," Fleita said. "He certainly deserved an opportunity and that's exactly what we're giving him. You're only as good as the people giving you information. It was spelled out to him that he's coming in to compete for a job and that he has to earn it.
"He'll be treated like everyone else in the organization."