Even if the guy was a 28-year-old intern.
"Ben said, 'Do you really want to do this? You know it will be a huge pay cut and you'll be an older intern,' " Hoyer recalled. "And I said, 'I don't care, I'll look at it as grad school, take on debt for a couple of years and if it works, great. If not, I'll have no regrets.' "
Regrets already had begun piling up after Hoyer hastily ditched his dream of working in sports after graduating in 1996. He had written every major league team looking for an opportunity but the history major struggled to open a door even a crack.
"I gave up too quickly and in hindsight wasn't as dogged as I should have been," Hoyer said. "But at the time, they weren't hiring a lot of people like me."
In the midst of an ownership change in November 2002, the Red Sox were different. They were daring and maybe a little desperate. Cherington joked that the 100-year-old organization "felt like a startup."
"There was a constant buzz of activity and we had a lot of fun along the way with Jed's creativity, judgment and humor playing a huge role in those early years," said Cherington, now a lecturer at Columbia University.
A week after Hoyer joined the Red Sox, the team named Theo Epstein _ three weeks younger than Hoyer _ its new general manager. The sports junkies clicked immediately, and before long the team's oldest intern had emerged as Epstein's most trusted ally. Epstein involved Hoyer in every detailed aspect of the Red Sox operation, from player development to sabermetrics to scouting. As Epstein kept elevating Hoyer until he was his top assistant, the pair became a formidable baseball brain trust, bonded forever by two Red Sox World Series titles.
"I'm indebted to Theo for early on putting me in charge of things I probably shouldn't have been," Hoyer said.
From Boston to Chicago, except for two underrated seasons as Padres general manager, Hoyer has spent his entire time as a baseball executive as an acolyte to Epstein. To be a general manager under Epstein, a magnet for attention he resists, the job description requires big ideas but a small ego. Hoyer meets both criteria, as affable as he is intelligent with a natural curiosity that makes him an easy conversationalist. He is the consummate sidekick, The Other Guy in the Cubs front office once kiddingly compared to a potted plant at news conferences because he did little more than contribute to the scenery sitting next to Epstein.
Talk about the Cubs around town and Jed only comes before Theo alphabetically, a reality Hoyer accepts without a hint of resentment.
"No, it doesn't bother me," Hoyer said. "One of the first things we talked about when we did this was that this only is going to work is if it's a total collaboration. No one knows who works on what deals or what contracts. Once you start getting into who deserves credit in a front office, it's a huge negative and we've done what we can to avoid that."
It helps that Hoyer holds his buddy in as high esteem as others.
"Listen, Theo is one of a kind," Hoyer said. "He has created an amazing culture and is as good of a baseball executive as this game has seen in long time. I'm fortunate I've been able to learn from him. We form a great partnership and know the way the other thinks. How I see it is, your ultimate goal in every sport is to be a good teammate and help your team win. ... I want to be that good teammate."
That's what Hoyer was at Wesleyan, where he still holds the single-season saves record and finished with 123 career hits as a shortstop versatile enough to play the outfield. He once was the starting pitcher for both games of a doubleheader _ and won both.
"A very good college baseball player and great competitor," Cherington said.
When Hoyer was a sophomore, Wesleyan lost to Wisconsin-Oshkosh and future major league pitcher Jarrod Washburn in the Division III World Series. As a senior, the 5-foot-9 Hoyer batted cleanup because he rarely struck out.
"I'd run out for introductions at 5-9 between our third and fifth hitters who were 6-3 and 6-4, and people must have thought I had the strongest hands of all time," Hoyer said. "But I just wanted to do whatever I needed to win. ... And I kind of feel like that about this job."
His job as GM of baseball's best team involves "anticipating fires," according to Hoyer, and offers him a rare shot at the kind of legacy in Chicago that Epstein already enjoys in Boston. Traveling there with Epstein in 2014 for the 10-year reunion of the 2004 World Series champions created a memory that left a deep impression.
"People were still coming up to Theo and saying, 'Thank you,' " Hoyer said. "You can't compare another championship in sports to that yet. Maybe if Cleveland wins an NBA title, but I really think the Boston experience and the Cubs experience, in terms of what it would mean to the fan base and culture, is exactly the same."
Does playing a bigger role here make the burden feel heavier?
"I wouldn't have taken this job if I believed in curses," Hoyer said, chuckling. "The wait till next year approach puts a lot of pressure on next year. I know this: If you keep making the playoffs year in and year out, one of those Octobers, it's going to be magical."