The World Series is over, and the cold already has set in across Chicago ballparks as free agency and winter fast approach – which could be almost the same thing for the Cubs.
Now what?
As free agency opens Monday, marking the start of MLB’s offseason, the Cubs face at least seven key questions to answer ahead of spring training:
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Keep Ian Happ or non-tender the former ninth overall draft pick?
The switch-hitting outfielder with a career .805 OPS is one of the most erratic streak hitters in the game and through July this year looked like a strong candidate to be non-tendered. A hot two-month finish (.294 with 15 homers and a .963 OPS over his final 54 games) probably saved him from the potential career setback.
But that bad-for-four-months-and-hot-for-two season performance also has been a pattern that’s hard to ignore – the four months representing his longest slump. Happ, who made $4.1 million after beating the team in arbitration, has never put together a full season of big-league performance that didn’t include deep slumps and raise red flags.
And if the team was willing to non-tender Kyle Schwarber a year ago over a projected salary of $8 million to $9 million, a decision on Happ either way would not be surprising, especially for a player that took the team to an arb hearing last winter.
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They have more payroll flexibility – by a lot – this time around, and Happ’s probably worth another role of the dice in his age 27 season. But for a guy who was hitting .177 with a .611 OPS until a few days after the trade deadline – with more strikeouts than hits and walks combined – the clock is ticking on Happ.
Which Cubs free agents should/will the team try to sign back?
The list isn’t exactly as star-studded as it looked before the deadline, with five mid- to low-level free agents heading to market in pitcher Zach Davies, infielder Matt Duffy and catchers Jose Lobaton, Austin Romine and Robinson Chirinos.
The intriguing player on the list is Duffy, who was a surprise non-roster invitee to make the Opening Day roster and then showed why until he hurt his back in late May, with a contact-hitting skills otherwise rare on the roster. He’s a smart, versatile player and good clubhouse guy, who could fill a role on a modest contract.
Chirinos is the other name on the list worth more than a glancing look, in large part because of a veteran presence that has been respected in clubhouses everywhere he has played, along with a still-productive skill set at 37. If he still plans to keep playing, he could fit as a depth piece at a key position.
Hey, what about Nick Castellanos?
What about him?
The one-time Cub sensation opted out of his contract with the Reds, with two years and $34 million left on the deal, making Castellanos, 30, one of the best bats on the market this winter.
But he’ll almost certainly get a qualifying offer from the Reds and be tied to draft-pick compensation for the team signing him, and he’s no better an all-around fit for the Cubs than he was the last time he was a free agent (two years ago, given his fielding limitations in the corner outfield spots. Not to mention what figures to be a very steep price for a Scott Boras client coming off a career year and his first All-Star appearance.
How big a priority is extending catcher Willson Contreras and avoiding the distraction of a lame-duck season that affected the team in 2021 with three big-name pending free agents (Javy Baez, Kris Bryant, Anthony Rizzo)?
The last high-value All-Star standing from the deadline purge, Contreras has one year left under club control after a workhorse season in which he made $6.65 million.
He has talked about wanting an extension – but also wanting to win. The Cubs have hinted around the idea of an extension, but it’s anything but clear what their timeline might be or their longer-term intent with a player who is also has the highest trade value among any of their veterans.
Trade him this winter? At the trade deadline next summer? Extend him and build around him and the handful of projectible young players in-house?
It could be the biggest decision they make this winter for not only next season but the entire rebuilding timeline.
Will the Mets ever find anyone to take their general manager job, and why should anyone in Chicago care?
The first part of that question is fast-becoming an industry-wide joke as high-profile targets – Theo Epstein and Billy Beane among them – have turned down the Mets’ overtures, and rival teams have refused to grant permission to interview other targets.
But the second part can be summed up mostly in two words: Javy. Báez.
What little chance the Cubs might have to engage Báez in talks to return to Chicago on a contract palatable to nickel-conscious ownership and a cost-analysis-driven front office starts with the Mets’ intentions with Francisco Lindor’s best friend in the game. And that starts with the next GM.
Not to mention a handful of other very intriguing Mets free agents, including outfielder Michael Conforto and pitcher Noah Syndergaard.
Will/should the Cubs sign any free agents before Dec. 2?
The significance of this date is obviously the 11:59 p.m., Dec. 1 deadline for the current Collective Bargaining Agreement and whether MLB will lock out the players as negotiating leverage and freeze transactions if a new deal isn’t in place.
Few in the game expect such a stoppage to result in time lost next spring or games lost during the season, but for a team like the Cubs, with a massive list of roster holes to fill, a freeze until, say, mid-January or February could have a disproportionate impact.
That’s especially true if team president Jed Hoyer is serious about his stated intent to compete for a division title next season.
That could make the three weeks of free agency before the deadline (starting Monday) a key time for at least a few targeted signings by teams with so many holes to fill – though Hoyer has made it sound a lot like he’d be more willing to wait for the more certain other side of a lockout.
How many free agents should the Cubs consider offering deals of at least four years? Five years or longer?
Hoyer promises to be active in free agency, but also has mentioned the Giants’ 2020-21 offseason as a model for smart moves and prudence. The Giants signed only two free agents to contracts of more than one year: pitcher Jake McGee for two years ($5 million) and infielder Tommy La Stella for three ($18.75 million).
That’s right, the headline acquisition of the winter for a team that went from the depths of the National League in 2020 to 107 wins this year was Tommy La Stella.
That’s probably a fitting bottom line on that subject – no matter how much the Cubs might want Carlos Correa or any of the high-demand starting pitchers on the market.