Will Theo Epstein Go Bold This Winter or Save Big Trades for Deadline?

The Yankees-Mariners deal involving starter James Paxton gave a shot of warmth to every hot stove enthusiast. Though the deal didn’t help the Cubs, fans surely hope it spurs trade activity that ultimately does address key needs. However, we must temper this with the realization that Theo Epstein doesn’t regularly make big offseason trades that substantially affect the big league roster.

The front office is of course always busy during the winter. Lots of minor league transactions, stockpiling of 4A sixth starters, and free agent signings. But in his seven years heading the Cubs, Epstein has mostly preferred to value-hunt in winter and save his best trade chips for the mid-year deadline season.

His most active offseason by far as a trader came that first winter, 2011-12. In four separate deals, Epstein shipped out Sean Marshall, Carlos Zambrano, Tyler Colvin, D.J. LeMahieu (then a prospect), and Andrew Cashner. Those deals largely fell into the change-of-scenery/value-hunting category, but they brought back Travis Wood, Chris Volstad, Ian Stewart and – the big one for Cubs history – Anthony Rizzo.

Epstein’s next-busiest winter of trades came before the 2015 campaign, when he once again surrendered ancillary pieces for veterans Dexter Fowler and Miguel Montero. The next offseason saw the Cubs move Starlin Castro for near nothing (Adam Warren) to make room for free agent Ben Zobrist. And then before 2017, Epstein again value-hunted successfully with his Jorge Soler-for-Wade Davis deal.

And that’s it. A pretty short list for seven years of winter meetings. So should we expect anything different this time around? Will Epstein continue to overvalue his trade assets only to overpay in July? Or will he work the cold-weather trade market with the kind of aggressive urgency he’s now demanding from his players?

Based on past behavior, you wouldn’t wager too much on significant deviation from his past record. However, a key variable has changed this year: The Cubs’ alleged payroll conservativeness. It is possible this factor will make Epstein more willing to deal. He may also want to prove to his roster that his “or else” words were more than mere threat.

Plus, with eager sellers like Arizona, Seattle, and probably Kansas City, the opportunity seems ripe to flip a couple young cost-controlled bats for (finally) young cost-controlled assets in other need areas. Namely the back end of the bullpen and at the leadoff spot.

Royals second baseman Whit Merrifield intrigues in that latter role, but the Cubs’ large number of flexible infield pieces and the Royals’ high asking price or reluctance to deal him at all may rule him out. The ideal target remains a fast, leadoff-hitting centerfielder, and all roads there still to lead back Mallex Smith, recently re-acquired by the Mariners from Tampa.

Fortunately, Seattle’s Jerry Dipoto is never one to label a recent trade acquisition untouchable. The two most attractive Seattle pieces are Smith and 24-year-old closer Edwin Diaz. One wonders if a package anchored by Kyle Schwarber, Victor Caratini, Adbert Alzolay and Alex Lange could land both Mariners.

Seattle would get back multiple assets back they need, as both Schwarber and Caratini are young and would get far more starts in Seattle than possible with the Cubs. Everyday playing time could increase their flip value for a subsequent deal, further multiplying Seattle’s asset return, or could just provide the Mariners with solid players.

From the Cubs’ end, Diaz and Smith would check two major boxes with young, long-term solutions. Epstein can then limit his free-agent signings to a veteran leader like Andrew McCutchen and one more bullpen piece. With that, the team would be set for spring training and the start of Yu Darvish Watch 2019 as we hope for his healthy return.

But it all starts with Epstein. What do you think? Will he continue to cling to his reluctance to deal during the winter or will he venture near the heat of the hot stove and go big?

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