At 41, Andy MacPhail was four years older than Theo Epstein when he came to Chicago to run the Cubs in the fall of 1994, but he too was every bit the baseball prodigy.
Like Epstein, MacPhail, a member of baseball's young elite, already had two World Series titles on his resume. MacPhail was also the last executive traded in baseball, arriving in Chicago in exchange for a Class A pitcher sent to Minnesota in compensation for the much-heralded hire by the Cubs.
"There were similarities," MacPhail agreed about him and Epstein, "but it was a different kettle of fish."
He was referring to the fact that when he left the Twins, he was on good terms with owner Carl Pohlad, happy in Minnesota, and left (he walked away from an offer of $4 million and part-ownership of the Twins) only after promising it would not be for the same job.
But there is something else, MacPhail said, that will be different for Epstein.
"I think Theo faces higher expectations of what has to happen on the field compared to what we had because the bar is higher," said MacPhail, who left the Baltimore Orioles earlier this month as president of baseball operations.
"Say what you want, but under Jim Hendry, the Cubs went to three postseasons, which was equal to 50 years prior. And economically, the [financial burden] on those people attending games is stiffer now."
MacPhail chuckled at the memory of being sent to Disney World with other Tribune execs for a seminar on customer relations after he arrived.
However long the honeymoon period lasts for Epstein, who will be formally announced on Tuesday as the Cubs president of baseball operations, with Jed Hoyer the team's new GM, it will be that much harder than it was for MacPhail.
The lure of bringing a World Series title to the North Side, however, remains just as powerful. But MacPhail said Epstein needs to take a deep breath and maybe even a small step back as he embarks on one of the most pressure-packed jobs in all of sports.
"I'm not big on giving advice, but you can't let too much of your persona get tied up in it all. You can't get seduced by that stuff," MacPhail said. "Of course you have to take your responsibility very seriously, but don't take yourself too seriously.
"Do what you have to do but there's so much pressure to take shortcuts. And if I had to give him any advice, it would be 'Don't look for shortcuts. Do what you have to do to get better and time will take care of itself.' The inclination is to look for the quick fix and it just gets stronger. But it's something you just have to resist. You just have to build your best chance of winning."
Though MacPhail certainly had his detractors for the lowlights in his time here (see: Todd Hundley, the handling of Mark Prior, the coddling of Sammy Sosa, three GMs, etc.), there was also no shortage of bad luck in Chicago while he was at the helm. He came in in the middle of a strike and was in charge during the Cubs' NLCS debacle of 2003.
Another criticism of the Cubs during MacPhail's regime was that he presided over a front office that was much too small by baseball's large-market standards, and it is still one of the smallest in baseball.
"Part of it was my philosophy that I'd rather have one guy too few than one guy too many," he said. "And in Wrigley Field, there wasn't space for two more people. We took over the donut shop and expanded public relations. We were somewhat restricted."
Epstein will surely expand, and already has with the eventual hiring of Hoyer, though he won't have the luxury of having the sort of money the Tribune Company threw around in its last years of ownership, when big-spending like the Alfonso Soriano's eight-year, $136 million deal all but paralyzed the Cubs.
The Tribune piled up plenty of cash while MacPhail was here, but not many victories.
"I never felt encumbered by the Tribune," MacPhail said. "The only time I was encumbered was toward the end when there was more pressure to make a higher profit because other companies [under the Tribune umbrella] were hemorrhaging money. But Jim Dowd and John Madigan, they all wanted to win. They all wanted to be the CEO responsible when the Cubs won."
Lord knows every person who has ever been associated with the Cubs has wanted the same thing.
"If Theo can be GM of the Red Sox and have that drought end, and be in the same place in a different league with the Cubs and have that drought end," MacPhail said, "that's pretty powerful stuff."
Melissa Isaacson is a columnist for ESPNChicago.com.