If and when Theo Epstein enters the Baseball Hall of Fame, he’ll have something to reminisce about besides breaking championship curses in Boston and Chicago.
When former Cubs pitcher (and current front-office employee) Ryan Dempster needed help preparing for his upcoming stint with Team Canada in the World Baseball Classic, he went right to the top. Epstein, the Cubs’ president of baseball operations, put on a batting helmet, jumped in the cage and took five at-bats against Dempster on Monday at the team’s spring training site at Sloan Park in Mesa, Arizona. According to CSN Chicago, Dempster threw about 50 pitches total to Epstein, Cubs infielder Tommy La Stella and minor leaguer Todd Glaesmann.
The perceived highlight of the Epstein-Dempster encounter appears to be subject to some debate.
“Theo said it looked very fast,” Dempster said by phone. “He takes instruction well, though. Eric Hinske, our hitting coach, told him, ‘When Demp gets ready to start picking his leg up, start swinging.’
“Third at-bat, ground single to left or groundball to short — depends who’s playing shortstop. Fourth at-bat, opposite field double. It was crushed, so I pimped it. Last at-bat, Demp wised up and threw me all splits and punched me out swinging. He still has a good split. And I still know my place … upstairs!”
“He did OK, though. He jammed one to third base and flared one to where the right fielder would be. Then I threw him some splits and he had no chance.”
Epstein agreed with all but one piece of Dempster’s assessment.
“Does this look like an opposite field flare?” he said in an email. In a subsequent email, Epstein broke down his batting practice session in detail.
“Well, I know I can’t hit major league pitching, but I wanted to see if I could hit Ryan Dempster,” he said. “First at-bat he jammed me twice — ground foul past third and a grounder to third. Second at-bat, he punched me out looking on a ball below the zone. I immediately released the catcher who was calling balls and strikes.
“Third at-bat, ground single to left or groundball to short — depends who’s playing shortstop. Fourth at-bat, opposite field double. It was crushed, so I pimped it. Last at-bat, Demp wised up and threw me all splits and punched me out swinging. He still has a good split. And I still know my place … upstairs!”
Epstein also conceded that his well-struck ball to right field might have gone for extra bases only under select circumstances.
“It was only a legit double if Steve Balboni was playing right field,” he said.
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