The art of the megadeal: Like Nationals, Cubs will have to sign their Werth

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The art of the megadeal: Like Nationals, Cubs will have to sign their Werth

The day is coming where the Cubs are going to force you to pay attention. Jay Cutler and Derrick Rose won’t dominate talk radio. The buzz won’t revolve entirely around the Bears and Bulls.

Team president Theo Epstein will hold up a white pinstriped jersey at a stadium club news conference. There will be a photo shoot in front of the ivy and outside the Wrigley Field marquee, selling the dream of a parade down Michigan Avenue.

This will be The Right Player at The Right Time.

The Atlanta Braves landed B.J. Upton on Wednesday with a reported five-year, $75.25 million deal. The Cubs won’t be making any $150 million investments next week during the winter meetings in Nashville, Tenn. But eventually they’re going to have to jump in and sign a free agent to a contract longer than one year, even if the splash messes up their precise definition of value.

It could happen sooner than you think. Just listen to Chicago guy Mike Rizzo explain the art of the megadeal, and you get an idea of how the Cubs might get it done.

Two years ago, on the eve of the winter meetings, Rizzo made a huge bet on Jayson Werth and sent shockwaves throughout the industry. The numbers seemed like pure fantasy at the Walt Disney World Swan and Dolphin Resort: Seven years at $126 million.

But it was all part of a carefully calculated plan for the Washington Nationals general manager. Dec. 5, 2010 would be a landmark day in franchise history.

“We were at the point (with) our young players (where) we saw them coming,” Rizzo recalled. “They weren’t going to be those impact players yet, but we saw those guys scratching the surface and we were convinced that they were going to be good, solid core pieces for us for a long time.

“We had just come off 59 wins and then 69 wins, so we had an uptick in improvement and we felt that we needed (something). There was very much a loser mentality there, a losing culture, not only in the clubhouse, but in all surrounding areas, and I wanted to cut that out.”

Relaxed after a season in which the Nationals won 98 games and the National League East, Rizzo rattled off the details during an interview earlier this month at the general manager meetings in Indian Wells, Calif.

The kid who grew up west of Wrigley Field on Waveland Avenue sketched out the kind of player the Cubs will chase.  

“Jayson brought us a veteran presence with a good skill set,” Rizzo said. “He was the two-way type of player that we were looking for. If you remember, at that time, we had guys like (Cristian) Guzman playing second and Adam Dunn was at first and we were very one-dimensional.

“We weren’t good defensively. We didn’t run the bases well. We could hit a home run with you, but it didn’t help our good, young pitchers that were coming up. (So) we wanted to get more athletic, more high-energy.”

Werth would turn 32 during his first season in Washington, but he had earned a World Series ring with the Philadelphia Phillies in 2008. He had emerged as a strong supporting outfield piece on teams that won four straight division titles. Big-money players have to be leaders.

“I was extremely comfortable with who the person was, the makeup,” Rizzo said. “I had scouted him since he was in high school. He’s an Illinois kid. I played in the minor leagues with his uncle, so I knew the kid backwards and forward.”

This is what Epstein means when he says the premier free agents have to check off (almost) all your boxes.

But it also means dealing with Scott Boras, because the super-agent shrewdly pushes his clients to the open market at a time where clubs are locking up their best players with extensions. And you have to pull the trigger, even if the timing isn’t exactly right.

“It was a year ahead of schedule,” Rizzo said, “because that player was there that year. We knew with the length of the contract, he was going to be with us when these guys really came into their own.

“With Bryce Harper on his way up, (Werth) was going to be one of the guys to take him (under his wing). Same agency, same position – he was going (to) mentor him to become a better player at a quicker rate, accelerate his developmental curve and we’d get our money that way out of him.”        

On the North Side, maybe that’s someone who will push Starlin Castro, protect Anthony Rizzo and teach Javier Baez.   

Rizzo estimated his major-league payroll was around $50 million that winter. The Nationals had Stephen Strasburg and Jordan Zimmermann lined up for their rotation, Ryan Zimmerman and Ian Desmond on the left side of the infield, and power arms like Drew Storen and Tyler Clippard out of the bullpen.

Werth had been an All-Star just once, never finished higher than eighth in the MVP voting and still hasn’t generated 100 RBI in a season. But this negotiation went beyond numbers.

“Most importantly, he was good on the field, off the field, in the dugout, in the clubhouse and in the community,” Rizzo said. “He brought us a winning attitude. After he sat down with ownership and myself, we were convinced that he was going to change the culture and he wasn’t going to allow us to be ‘the losing Nats.’

“We knew we had some money to spend. He was our No. 1 target and we went hard after him. To convince him to come to a 59-, 69-win team, we had to overpay him. But he fit the criteria that we wanted.”

Werth broke his wrist last May, but came back as a leadoff hitter, grinding out at-bats for a team that looks like a contender for years to come. The Nationals were so self-assured that they shut down Strasburg as a precaution in his full recovery from Tommy John surgery.

“We have a philosophy,” Rizzo said. “It was a difficult time for me personally, and for the organization, to take the heat for that decision, but that’s what I get paid for. You take the arrows for the manager and ownership and everything else.

“I felt at ease with the decision the whole time, and I still do. (But) the furor in the industry – (the decibels from) the analysts and the experts – (that) surprised me a little bit.”

The Cubs aren’t doing shock and awe yet. They will have to stick to their plan, but deviate when necessary. They need to study the deals from every angle, without experiencing paralysis by analysis. They will need to identify the missing piece – and then block out all the noise.  

Brett Anderson’s main takeaway from Cubs pitching coach Chris Bosio

Brett Anderson’s main takeaway from Cubs pitching coach Chris Bosio

MESA, Ariz. – The pitching section of The Cubs Way manual might not be spelled out this way, but it can be summed up in five words: Have 'em work with Boz.

Or at least that's how it sounds whenever the Cubs add another fading prospect or injury case, rolling the dice on raw stuff, change-of-scenery psychology and the wizardry of pitching coach Chris Bosio.

While the Theo Epstein administration is still waiting on the drafted-and-developed pitchers to put around the Wrigley Field marquee next to the images of sluggers Kris Bryant and Kyle Schwarber, the Cubs already have the infrastructure in place that helped turn Jake Arrieta into a Cy Young Award winner and transform Kyle Hendricks into an ERA leader.

One of Bosio's ongoing projects is Brett Anderson, who underwent surgery to repair a bulging disc in his lower back last March, yet another injury in a career that hasn't lived up to his own expectations.

"It's one of those things where he's not trying to reinvent the wheel," Anderson said. "It's more trying to limit the pressure on my back and mild mechanical adjustments where I don't land on my heel as much and kind land on the ball of my foot or my toes, so it's not such a whiplash effect.

"He's had a good track record with health, especially the last couple years, and hopefully I can fall in line there, too."

Anderson made it through his first Cactus League outing, throwing a scoreless first inning during Monday's 4-4 tie with the White Sox in front of another sellout crowd at Sloan Park in Mesa. The Cubs are taking a calculated risk here with a one-year, $3.5 million that could max out with $6.5 million more in incentives if Anderson makes 29 starts this season.

[MORE CUBS: How Ryan Dempster wound up on Team Canada for World Baseball Classic]

The Cubs can put the best defensive unit in the majors behind a lefty groundball pitcher and don't need to make a dramatic overhaul with a guy who grew up around the game. Anderson's father, Frank, is an assistant at the University of Houston and the former head coach at Oklahoma State University.

"I've been going to the field since I could walk and talk and annoy college kids," Anderson said. "I could take that one of two ways: I could get burnt out quick and kind of shy away from baseball. Or I could eat it up. Fortunately for me, I've eaten it up all the way through."

The entire question with Anderson revolves around health. He won 11 games for the Oakland A's in 2009 – finishing sixth in the American League Rookie of the Year voting – and hasn't topped that number since. There's been a Tommy John surgery and disabled-list time for a stress fracture in his right foot, a broken left index finger and a separate surgery on his lower back.

"If you dwell on the negative, you're going to worry yourself sick," Anderson said. "Pitching's fun – good, bad or indifferent – (so) you have to have a positive outlook, because otherwise you just walk around with a black cloud over your head."

The only other time Anderson hit the 30-start mark would be 2015, when he threw a career-high 180.1 innings, put up a 3.69 ERA and led the majors with a 66.7 groundball percentage. He couldn't repeat that performance with the Los Angeles Dodgers, accounting for 11.1 innings last year and not making the roster in either playoff round.

The "hybrid" fifth/sixth starter idea manager Joe Maddon floated sounds good in theory and we'll see how it works with Anderson and Mike Montgomery and a veteran rotation with strong opinions and clear ideas about routines. But the Dodgers needed 15 different starting pitchers to survive the 162-game marathon last year and seemed to run out of gas by the time the National League Championship Series returned to Wrigley Field.

"You can't have too much depth coming from where I was last year in L.A.," Anderson said. "We used so many starters. Obviously, that wasn't really the case here, which you can't really bank on year in and year out. But if I'm healthy, everything else will work itself out and I'll take my chances.”

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."