"I would beg him to let me do anything for him," McLeod said. "I kept bombarding him to let me help him out."
The door eventually swung open for McLeod, and it did so again on Friday, when his first employer, the San Diego Padres, hired him away from the Boston Red Sox to be the new vice president and general manager of scouting and player development.
McLeod worked for six seasons in Boston with new general manager Jed Hoyer, who on Friday said he was happy to bring McLeod back home to San Diego, where he was raised and played his baseball in nearby Vista.
"I'm thrilled to bring Jason on board," Hoyer said. "Building up scouting and player develop is my No. 1 goal here. Hiring Jason is a huge step in that direction."
McLeod comes to the Padres -- comes back to the Padres -- with a reputation with the Red Sox and in baseball for presiding over several bountiful First-Year Player Drafts during his time as director of amateur scouting, a position he held since 2004.
McLeod's Drafts have included such homegrown talent as center fielder Jacoby Ellsbury and pitchers Daniel Bard and Clay Buchholz, among others. He was also largely responsible for the scouting and recommendation of 2008 American League MVP Dustin Pedroia.
"I think all you have to do is look out on the field [in Boston] to see his success," Hoyer said. "He's a great evaluator. He was someone [Red Sox GM Theo Epstein] leaned on heavily to make evaluations."
These, certainly, are the kind of results Hoyer and McLeod would like to see here with the Padres, especially given the track record the team has had with many of its top draft picks, who, for various reasons, haven't panned out.
To get there, the process starts with information gathering.
"We were very information driven there [Boston]; we always felt the more information you had, the better decisions you're going to make," McLeod said. "We're always trying to learn and get better, learn from your success and your mistakes."
McLeod won't exactly ease into his new position. On Sunday, he, Hoyer and several members of the front office will head to Indianapolis for the start of the Winter Meetings.
McLeod also needs to make two important hires.
"We still have some staffing issues that we need to resolve," McLeod said. "We don't have a scouting director at this time, and we don't have a farm director. I think we'll start from there.
"Slowly but surely, I need to soak in as much information as I can. I'm not going to come in here and say I have all the answers."
McLeod, a Rancho Buena Vista graduate, was a 44th-round Draft pick of the Houston Astros in 1991 as a right-handed pitcher. McLeod is the grand-nephew of Hall of Fame pitcher Carl Hubbell.
McLeod worked for the Padres for 10 years in various capacities, including for the team in its stadium operations department, which included such tasks as posting signs in and around Qualcomm Stadium, shuttling people to their cars and about everything that fell under the guise of daily event planning.
Many of the people he worked with are still with the Padres.
"San Diego is my home," McLeod said. "I had the great fortune of working with a lot of great people here."
In Boston, McLeod was hired as the Red Sox director of scouting administration in 2003. His first Draft with the Red Sox was in 2004, one that produced Pedroia.
Under McLeod's watch, Baseball America has ranked the Red Sox's Draft among the top five in three of his first four years as director of amateur scouting.
This past offseason, he was voted the Red Sox Unsung Hero by the Boston Chapter of the Baseball Writers Association.
McLeod replaces Grady Fuson, who was dismissed after the season as the Padres vice president of scouting and player development.