After making qualifying offers, now comes the hard part for Cubs, Jake Arrieta and Wade Davis

After making qualifying offers, now comes the hard part for Cubs, Jake Arrieta and Wade Davis

Making qualifying offers to Jake Arrieta and Wade Davis before Monday’s 4 p.m. deadline might have been two of the easiest decisions the Cubs will face all winter.

It guaranteed draft-pick compensation if the Cy Young Award winner and the All-Star closer decline the one-year, $17.4 million contract offers within the next 10 days – and that looks like obvious moves given their reputations and strong platform seasons – and sign elsewhere as free agents.   

Now comes the hard part for two 30-something pitchers and a front office that needs to do a lot of heavy lifting for a team that has won 292 games, back-to-back division titles, six playoff rounds and a World Series across the last three seasons.

We’ll find out how close super-agent Scott Boras can get to his bulletin-board quote from Opening Night 2016, when Arrieta set the tone for a championship season with seven scoreless innings in a 9-0 win at Angel Stadium of Anaheim: “Every Cy Young Award winner I know got a seven-year contract.”

We’ll see if last winter’s record-setting deals for closers become the norm – or an anomaly – after another October where relievers took center stage and managers constantly got second-guessed for those bullpen decisions.

Don’t expect anyone to hand Arrieta a megadeal that runs through his age-38 season, but this a top-of-the-rotation starter who won almost 70 percent of the time with the Cubs (68-31, 2.73 ERA), put up a 3.08 ERA in nine career playoff games and took control of his career by developing his own training program and visualization process.       

As someone who notched the final out of the 2015 World Series for the Kansas City Royals, went 32-for-33 in save chances as a Cub and threw 92 pitches (!!!) combined in his last two playoff appearances, it wouldn’t be unreasonable for Davis to shoot for Mark Melancon’s four-year, $62 million contract (a deal the San Francisco Giants must already regret).  

[MORE: For the second straight year, Munenori Kawasaki is a world champion]

You know the Cubs will stay in touch with the Arrieta and Davis camps – just in case a certain market doesn’t develop or a player is left out in the cold – because that’s how this front office operates and how much this team needs pitching.

“We’d love to have Wade Davis back, and same with Jake,” team president Theo Epstein said the day after the Los Angeles Dodgers bounced the Cubs from the National League Championship Series. “They’re two quality pitchers, guys who are elite at what they do and have tremendous track records.

“When it comes to free agency – and starting to talk about prospective free agents – I always stop and recognize just how hard it is to get to free agency and how much work these guys put in to get to this point.

“It’s a right that they’ve earned and that they deserve. You may only get one crack at it in your whole career. It’s an important time for them. They have to do what they should do to put themselves in a great position going forward with their families.

“From our end, it’s easy to sit here and say we’d love to have them both back, because we would, for what they do on the field, and for what we think of them off the field, and what they contribute off the field. But it’s a lot more complicated than that.”

Just look at next season’s projected arbitration salaries on MLB Trade Rumors and the rising costs for 2016 NL MVP Kris Bryant ($8.9 million), World Series Game 7 starter Kyle Hendricks ($4.9 million) and All-Star shortstop Addison Russell ($2.3 million).

Keep in mind next winter’s banner class of free agents, which includes Bryce Harper and Manny Machado and potentially Clayton Kershaw and David Price.         

This is also where the Cubs are going to feel the squeeze from the final six years of Jason Heyward’s $184 million contract. World Series MVP Ben Zobrist will make $28 million combined during his age-37 and -38 seasons, possibly as a part-time player. Jon Lester is only halfway through his totally-worth-it $155 million contract and the Cubs already know how nine-figure deals for pitchers usually end.  

So it won’t be a surprise if the Cubs try to trade for and coach up the next Arrieta, and get a little more creative with the ninth inning than simply making Davis an offer he can’t refuse.    

“You have tough choices to make,” Epstein said. “We have a lot of players getting to a different point in their careers with respect to salary structure and players getting raises. And looking even beyond next year, and considering future free-agent classes and different things we need to do to try to keep this consistent winner (going).

“We’re going to go in open-minded with an obvious desire to keep both guys, but knowing it will be complicated and seeing what we can do.”

Looking ahead with Jon Lester as Cubs try to reload for another World Series run

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USA TODAY

Looking ahead with Jon Lester as Cubs try to reload for another World Series run

Jon Lester could never pick up a baseball again and the Cubs would still be satisfied with their $155 million investment. The parade down Michigan Avenue will always be worth it.

But 362 days later, Lester isn’t ready to spend all his time hunting in Georgia and playing celebrity golf events. The Cubs still absolutely need Lester’s presence and credibility. Not to prove that this franchise is serious about winning — the way his decision to sign with a last-place team after the 2014 season accelerated the rebuild — but to again anchor a rotation that might be at its most vulnerable point since those summers of flip deals.

Super-agent Scott Boras wants to keep all big-market teams in play for leverage — and Jake Arrieta is too savvy to completely rule out a return — but signs point to the Cy Young Award winner getting his nine-figure megadeal somewhere else. The expectation is John Lackey will retire and become the anti-David Ross, only popping up in Twitter photos when his family goes trick-or-treating with the Arrietas and Tommy La Stella. The farm system isn’t producing internal solutions anytime soon.

That leaves Lester, Kyle Hendricks, Jose Quintana and two giant question marks for this winter, the Cubs likely pursuing one free-agent starter (Alex Cobb?) and trading from their surplus of hitters (Ian Happ?) to get a young pitcher and continue the momentum from three straight trips to the National League Championship Series.

“Everybody involved has done nothing but deliver on their promises to me when I signed here,” Lester said, crediting by name chairman Tom Ricketts, team president Theo Epstein, general manager Jed Hoyer and manager Joe Maddon after the Los Angeles Dodgers dismantled the Cubs in the NLCS.

“I know you guys are probably sick of me by now, but I’ve got a guaranteed three more to go, so suck on that one,” Lester said, cracking up the reporters surrounding his locker inside the Wrigley Field clubhouse. “Hopefully, in those next three years, we’re able to maybe win another one or two. That’s up to these younger guys to carry my load on that one.”

Lester has credited Hendricks for the unmatched preparation that made him the Game 1 starter against the Washington Nationals in the first round of the playoffs, and raved about Quintana’s work ethic and personality since getting traded from the White Sox during the All-Star break.

But even with the blockbuster Quintana deal, the Cubs are still bracing for the possibility of replacing 40 percent of their rotation, at a time when Lester is about to turn 34 and coming off a season where he put up his lowest number of innings (180.2) since 2007 (when he was still recovering from a cancer diagnosis and lymphoma treatments). Lester’s 4.33 ERA was almost exactly the league average and his trip to the disabled list in the middle of August/early September was his first since 2011.

“Halfway through, I think we’re really happy with the first half of that deal,” Epstein said. “It’s been a really nice success for him and for us. That’s really the half of the deal that’s the key when you make those kinds of deals. If you don’t get return on the first half, you’re probably in trouble.

“You better get production in the first half of those deals — or it’s going to end up being a big mistake.”

The Cubs hope Lester can model Andy Pettitte, the left-handed pitcher he’s been compared to since coming up with the Boston Red Sox. Pettitte got some, uh, help, admitting to using human growth hormone while recovering from an elbow injury in 2002, his reputation stained in the Mitchell Report. But the overall picture of Pettitte is someone who won four World Series rings with the New York Yankees, accounted for 276-plus innings in the playoffs and started 30 times during his age-41 season.

No matter what happens from here, Lester has been worth every penny. No one else in the big leagues has made at least 30 starts in each of the last 10 seasons. He essentially averaged a strikeout per inning this season and is only a year removed from finishing second in the NL Cy Young vote.

“In Jon’s case, look, he still has all the characteristics that we think make him an effective pitcher and a reliable bet going forward,” Epstein said, “because his mechanics are still sound. His arm — he had a little bit of shoulder fatigue — but bounced back from that. Knock on wood, he’s avoided any kind of significant injury.

“He’s shown the ability to pitch — and pitch effectively —  without his best stuff on certain days when he doesn’t have it. He had a few uncharacteristic really rough outings this year and was prone to the long ball more than normal.

“But besides that, he had some really nice stretches where he was sort of everything we hoped he could be. We’re counting on him to be a really big part of our pitching staff moving forward.”

The bottom line is that Lester has guts and the Cubs have faith that he will somehow figure out a way to compete. He shut down Washington for six innings in Game 2, leaving with a 2-1 lead before a bullpen meltdown at Nationals Park. He retired the first 10 Washington hitters he faced as a Game 4 reliever at Wrigley Field, a sign of how much the Cubs wanted to win that day. Three days later, he exited a 1-1 NLCS game at Dodger Stadium in the fifth inning, which will be remembered for Justin Turner’s three-run walk-off homer against Lackey.

This will be an opportunity for Lester to show even more of his personality, take on a more vocal leadership role, work with a new pitching coach (Jim Hickey) and maybe even cement his spot in the Hall of Fame with another World Series run.

“I don’t really care what people say about me on the field,” Lester said. “I may be an a------. I may show my emotions too much. I might show up the umpire too many times. I may yell at hitters. I don’t really care. But in this clubhouse — with my guys and my team — that’s what drives me.

“When I walk away from this game — just like if John Lackey walks away — (I want) everybody in this clubhouse (to) say the exact same thing: ‘That sumb---- had our back.’

“At the end of the day, man, the stats and all that other BS, that’s great. But that’s what I want. That’s what I want my guys to say about me.”

Offseason of change begins with Cubs firing pitching coach Chris Bosio

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USA TODAY

Offseason of change begins with Cubs firing pitching coach Chris Bosio

"Of course," Cubs manager Joe Maddon said in the middle of the National League Championship Series — he would like his coaches back in 2018. Pitching coach Chris Bosio told the team's flagship radio station this week that the staff expected to return next year. President of baseball operations Theo Epstein didn't go that far during Friday afternoon's end-of-season news conference at Wrigley Field, but he did say: "Rest assured, Joe will have every coach back that he wants back."

That's Cub: USA Today columnist Bob Nightengale first reported Saturday morning that Bosio had been fired, a source confirming the team declined a club contract option for next year and made a major influence on the Wrigleyville rebuild a free agent. Epstein and Bosio did not immediately respond to text messages and the club has not officially outlined the shape of the 2018 coaching staff.

Those exit meetings on Friday at Wrigley Field are just the beginning of an offseason that could lead to sweeping changes, with the Cubs looking to replace 40 percent of their rotation, identify an established closer (whether or not that's Wade Davis), find another leadoff option and maybe break up their World Series core of hitters to acquire pitching. 

The obvious candidate to replace Bosio is Jim Hickey, Maddon's longtime pitching coach with the Tampa Bay Rays who has Chicago roots and recently parted ways with the small-market franchise that stayed competitive by consistently developing young arms like David Price and Chris Archer.

Of course, Maddon denied that speculation during an NLCS where the Los Angeles Dodgers dominated the Cubs in every phase of the game and the manager's bullpen decisions kept getting second-guessed.

Bosio has a big personality and strong opinions that rocked the boat at times, but he brought instant credibility as an accomplished big-league pitcher who helped implement the team's sophisticated game-planning system.

Originally a Dale Sveum hire for the 2012 season/Epstein regime Year 1 where the Cubs lost 101 games, Bosio helped coach up and market short-term assets like Ryan Dempster, Scott Feldman, Matt Garza and Jeff Samardzija. 

Those win-later trades combined with Bosio's expertise led to a 2016 major-league ERA leader (Kyle Hendricks) and a 2015 NL Cy Young Award winner (Jake Arrieta) plus setup guys Pedro Strop and Carl Edwards Jr. and All-Star shortstop Addison Russell.

Bosio helped set the foundation for the group that won last year's World Series and has made three consecutive trips to the NLCS. But as the Cubs are going to find out this winter, there is a shelf life to everything, even for those who made their mark during a golden age of baseball on the North Side.