Cubs

Cubs: How Ryan Dempster wound up on Team Canada for World Baseball Classic

Cubs: How Ryan Dempster wound up on Team Canada for World Baseball Classic

MESA, Ariz. – During an escalating prank war, Ryan Dempster once arranged for a camera crew to shadow Will Ohman in spring training and sell the journeyman reliever on being the star in a TV special.

But Dempster isn't trying to punk anyone by playing for Team Canada in the World Baseball Classic – even though he's almost 40 years old and hasn't pitched in a competitive environment since Game 1 of the 2013 World Series at Fenway Park.

Don't let the Harry Caray/Will Ferrell impersonations fool you. Dempster always had a different side to his personality, an edge that allowed him to recover from Tommy John surgery, transition from 30-save closer back to All-Star starter and throw nearly 2,400 innings in The Show.

Still, it sort of felt like a reality show or a time machine or a spin-off from a Kris Bryant Red Bull ad on Monday at Field 1, the most secluded spot to throw live batting practice at the Sloan Park complex. On a cool, gray day, Dempster looked the same with his reddish beard, glove waggle, white pinstriped pants and blue Nike cleats.

Before stepping into the batter's box, Cubs president Theo Epstein tried to talk a little trash with Dempster: "I know I can't hit big-league pitching, but I'll see if I can hit you."

Besides Epstein, the eclectic group of hitters included Tommy La Stella and minor-leaguer Todd Glaesmann. Dempster threw roughly 50 pitches to Lance Rymel, a former farm-system catcher who will manage a Dominican summer league team this year. The audience included one reporter, six fans, a group of curious Cubs staffers and reliever Jim Henderson, who is in camp on a minor-league deal and will also pitch for Team Canada.

"I'm not going to be disrespectful to the whole process," Dempster said. "I'm not just like playing in a beer league and then decide: 'Eh, I'll throw against the Dominican team. The U.S. looks like they're pretty stacked, but I'll be all right.' I know what it entails going into this.

"At the end of the day, I'm not so worried about velocity. I'm worried about command and my ability to change speeds. It has been pretty funny to see the reactions, and I can understand why people would see it as far-fetched. But I always liked a good challenge."

Dempster first hatched this idea during a Fourth of July vacation, somewhere around Sequoia National Park in California. The group included Ted Lilly – another pitcher who got by with guts and became a special assistant in Epstein's front office – and former bullpen catcher Corey Miller.

"I just said: 'For old times' sake, why don't I throw a side?'" Dempster recalled. "I thought for sure when I woke up the next day I wouldn't be able to lift my arm up. And it felt really good."

Dempster continued with a throwing program – even through a trip to Hawaii after the World Series – and contacted Greg Hamilton, the head coach and director of Baseball Canada. As a Cub, Dempster had been the one leading runs up Camelback Mountain and showing younger pitchers like Jeff Samardzija how to train for 200 innings.

"I wasn't sure if he was serious or not," said Epstein, who did make contact against Dempster. "And then when I figured out he meant it and had a plan, I knew he'd be fine, because he's such a hard worker and he's really smart. If he's going to put the time in to get ready, I knew he'd be fine. He'll be competitive, for sure."

Dempster understood how to put together his own program with a focus on his legs, strengthening his core and shoulder exercises. To be clear, this isn't setting the stage for a comeback, the way game-over closer Eric Gagne is hoping to use Team Canada as a launching pad (after not pitching in the big leagues since 2008).

"This is just a chance to represent my country," said Dempster, who grew up in British Columbia and played on junior national teams in the 1990s. "Sometimes – I'm not bored – but a challenge in life or an opportunity presents itself. (And) it's a good lesson to teach my kids: If you work hard at something, you can do (it) and hopefully it pays off."

Dempster went out on top as a World Series champion, walking away from $13.25 million rather than pitch for the Boston Red Sox in 2014. He signed on with MLB Network and rejoined the Cubs as a special assistant in baseball operations. If he had to pick a lane, it would probably be entertainment and building off his Cubs Convention late-night format and sketches like "The Newlywed Game" with Epstein and general manager Jed Hoyer.

But Dempster still needs a fix. The star-studded cast from the Dominican Republic – Robinson Cano, Manny Machado, Adrian Beltre, Jose Bautista, Nelson Cruz – will be waiting on March 9 at Marlins Park.

"Major League Baseball, professional sports aren't a normal job," Dempster said. "How do you go from that extreme high, the adrenaline rush of going out there and pitching in front of 40-grand every day to…now what do you do that satisfies you? I'm trying to find that, make my way towards that. I feel like I will eventually get there."

Cubs' starting pitching a reasonable discussion topic, but Jon Lester's no fan of 'nitpicking' this first-place team

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USA TODAY

Cubs' starting pitching a reasonable discussion topic, but Jon Lester's no fan of 'nitpicking' this first-place team

WASHINGTON, D.C. — The Cubs are in first place, they own the best record in the National League at the All-Star break and remain as much a World Series contender as any team out there.

But things are never 100 percent rainbows and lollipops for a team with this high a profile.

No, instead of a simple thumbs up from fans and observers, a pat on the back and a “job well done,” there’s been quite a bit of focus on what’s not going well for the North Siders. Mostly, that’s meant starting pitching, as four of the team’s five Opening Day starters owns an ERA north of 3.90.

If all you’ve heard this season is “What’s wrong with Yu Darvish? What’s wrong with Jose Quintana? What’s wrong with Kyle Hendricks? What’s wrong with Tyler Chatwood?” you might think the Cubs are woefully underachieving. Instead, they’re 55-38, a first-half record not far off from what they owned at the break back in 2016, a season that ended in a curse-smashing World Series championship.

The lone Cubs starting pitcher at the All-Star Game, Jon Lester, isn’t happy with what he calls the “nitpicking” that’s come with the Cubs’ otherwise excellent start to the season.

“We’re kind of pulling at hairs,” he said before the Midsummer Classic on Tuesday night. “We’re splitting hairs right now as far as things that we’re looking for negatively on our team. And that can kind of rub wrong in the clubhouse as far as guys looking around going, ‘Wait a second, we’re doing pretty good and we’re getting nitpicked right now.’

“I don’t like nitpicking. So I feel like we’ve been doing really well and just stay with the positives of everything that we’ve been playing really good baseball.”

Lester’s got a point, though at the same time it’s an understandable discussion topic: If the Cubs aren’t getting consistent results from four of their five starting pitchers, what kind of effect will that have in a playoff series? There’s a long way to go before things get to that point, but Cubs players made their own expectations known back in spring training: It’s World Series or bust for these North Siders.

Lester has been phenomenal, unquestionably worthy of his fifth All-Star selection. He posted a 2.98 ERA in 19 first-half starts. But the rest of the rotation wasn’t nearly as pretty. Hendricks finished his first half with a 3.92 ERA, Quintana with a 3.96 ERA, Chatwood with a 5.04 ERA and Darvish, who made only eight starts before going on a seemingly never-ending DL stint, with a 4.95 ERA. Mike Montgomery, who’s made nine starts, has a 3.91 ERA overall and a 3.20 ERA as a starter.

None of that’s exactly end-of-the-world bad, and there are plenty of pitching staffs across baseball that would probably make a trade for those numbers in a heartbeat. But is it the elite, best-rotation-in-baseball type stuff that so many projected for this team before the season started? Of course not. And Lester knows it. He, like team president Theo Epstein, just looks at that fact a little differently than the fans and observers who are so quick to push the panic button.

“Can we pitch better? Absolutely. As a collective unit, yeah we can. And that’s a positive,” Lester said. “I think guys are ready for runs. You kind of saw Kyle put together a couple starts there where he’s back to being Kyle. Q’s been throwing the ball pretty well for us.

“I think this break will do Chatwood a lot of good. This is a guy, he’s pounding his head against the wall, beginning of the season he wasn’t giving up any runs but everybody’s talking about walks. I look at the runs, I don’t care about the walks.

“We get these guys back to relaxing and being themselves, we’ll be fine. Our bullpen’s been great, our defense has been great. Offense is going to come and go, as we’ve seen in the game. As starters, we’ve got to keep our guys in the game the best we can, at the end of the day our bullpen and our defense is going to pick us up.”

The fretting will likely never end unless the Cubs have five starters throwing at an All-Star level, that's just the way things go. Something’s got to fill all that time on sports radio, after all, and for a team with postseason expectations, it’s perfectly reasonable to talk about how they might fare in the postseason, where those starting-pitching inconsistencies will most definitely come into play.

But Tuesday night, Cubs fans will see three players representing their club. Lester will be a happy observer with one of the best seats in the house, and Javy Baez and Willson Contreras will deservedly start among the best in the game. And they’ll have bragging rights over all their NL teammates because nitpicking or not, they’ve got the best record in the league.

Cubs Talk Podcast: Are the Cubs World Series bound? Dan Plesac says yes!

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USA TODAY

Cubs Talk Podcast: Are the Cubs World Series bound? Dan Plesac says yes!

Where does MLB Network's Dan Plesac place the Cubs in his current power rankings and what's the key to their World Series dreams? Plus, which three star athletes mix to make Javier Baez? The conductor of the Big Blue train is back for a mid-summer breakdown of the Northsiders with Luke Stuckmeyer on this edition of the Cubs Talk Podcast presented by Wintrust.  

Listen to the full episode here or via the embedded player below: