Dempster pitched as a reliever and a starter for the Cubs from 2004-12, compiling a record of 67-66 with 87 saves.
After the Blackhawks won the first of their three recent Stanley Cup championships, in 2010, they brought the Stanley Cup to Wrigley Field and paraded it around the ballpark before posing for photos before a game between the Cubs and the Chicago White Sox. Dempster found himself front and center in the photograph near the pitcher’s mound. He also followed orders given by Blackhawks captain Jonathan Toews.
“It was unreal,” he said. “They come on the field. The White Sox are there. We were good. The White Sox were good. The Blackhawks were great. There was, at that time, really just an amazing Chicago sports scene going on. Now they come to Wrigley with the Cup.
“A couple nights before that, I went out with the (Blackhawks) guys with the Cup and got to know a bunch of them. I was sitting there on the mound, do the (ceremonial) first pitch. Jonathan Toews says, ‘Here.’ I said, ‘Here? What do you mean, here?’ He says, ‘Pick it up.’ I said, ‘Ahh, I know the rules. I’m not supposed to. I didn’t win the Cup.’ He goes, ‘Yeah, but if you don’t, 40,000 people are going to boo you. I suggest picking it up.’ When the captain tells you to raise the Cup, then let’s go.”
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