And despite the Cubs' legendary 103-year World Series drought, and accompanying pressure that surprised the likes of Dusty Baker and Lou Piniella, Walker believes Epstein has what it takes to meet the challenge and succeed.
"He came from Boston," Walker said Thursday on "The Waddle & Silvy Show" on ESPN 1000. "There is no bigger pressure cooker than Boston."
Walker played with the Cubs from 2004 to 2006. He arrived the year after they advanced to the NLCS before falling to the Florida Marlins, and he left the year before back-to-back division titles. So Walker saw firsthand a transformation of Cubs fans from accepting "Lovable Losers" to demanding more success.
"The Cubs got a little taste of winning and they have a little feeling for it, so now there is a little Boston feeling that, 'Man, we just want to win,' " Walker said. "So yes, absolutely, Theo understands that, because he came from Boston. There is no greater pressure cooker than New York or Boston. And so I think he's set up for success, and I think he'll do well."
Epstein and the Cubs have agreed to a five-year deal, believed to be between $15 million to $20 million, according to sources, and compensation for Boston releasing Epstein from his contract appears to be the only stumbling block before the deal is finalized.
Walker said he was Epstein's first acquisition when both joined the Red Sox in 2003
"I got to know Theo. He lived across the hall from me in our apartment complex in the Back Bay of Boston, and we got to talk a lot, and the guy knows baseball," Walker said. "The main thing is you grow them from the minor leagues, they come through your system, you don't take the easy way out and buy free agents and it seems like that's what Chicago has been doing. It hasn't worked out too well for the Cubs.
"He wants to grow from the system, which is the most economical way to do it. Also the best way to do it. In Boston, he had [Dustin] Pedroia, and he had [Jon] Lester. I think ultimately you have to grow through the system, and three or four of those guys who are superstars now in Boston -- [Kevin] Youkilis -- grew in the system and I think that's a credit to Theo."
Walker tried to imagine how Epstein would be perceived if he followed up his success in Boston by ending the drought in Chicago.
"For Theo, he controlled two World Series in Boston after they hadn't won it since 1912 (actually 1918) and now he comes to Chicago," Walker said. "Can you imagine if he would win a World Series in Chicago? He'd be the baseball czar.
"He's in a great position, because if he doesn't do it, well it hadn't happened in a 100-some-odd years, whatever. If he does do it, he is baseball czar. That's a good position to be in."