Five burning questions for MLB's Winter Meetings

It’s not yet time to suggest baseball’s offseason will move at a pace much quicker than a tugboat. Yet for the first time in several years, the game’s Winter Meetings may actually provide significant movement.

As Major League Baseball executives, agents and myriad power brokers set off for San Diego and the industry’s annual four-day bazaar of the bizarre, memories of the past two glacial winters are fresh and all too grim. And with two years remaining before the game’s collective bargaining agreement expires and either inspires wholesale changes or a work stoppage, there once again will be dozens of employable veterans still seeking jobs as spring training begins.

But with moderate action already unfolding on the free agent market – witness the Phillies landing Zack Wheeler and 30-plus vets Cole Hamels and Mike Moustakas finding homes – there’s reason to believe this year’s meetings may be more than just parlor talk. A look at the burning questions ahead of them:

What’s on Stephen Strasburg’s mind?

For the second consecutive year, the Winter Meetings will unfold in the hometown of a Washington Nationals legend seeking a nine-figure commitment and lifetime contract.

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And this time, there should be more actual suitors for San Diego’s Stephen Strasburg than Las Vegas native Bryce Harper.

He’s been a National since they made him 2009’s No. 1 overall pick, opted against free agency once by signing a $175 million extension, but then exercised an opt-out clause at just the right time. Strasburg, 31, struck out a career-best 251, won 18 games in pitching a National League-best 209 innings and then was the Nationals’ most indispensable cog in their run to a World Series title.

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It was generally presumed that Strasburg, a man of impeccable routine who moved full-time to D.C. a year ago, would return to the Nationals on a lengthier deal that included less deferred money than his old pact, which ran through 2023. But now we are a month past his opt-out date, the starting pitching market is already overheated and deep-pocketed clubs like the Phillies and Yankees and Dodgers are preparing their pitches.

If so inclined, Strasburg can break the bank.

Oh, he might not reach Gerrit Cole’s financial strata, but a deal north of $200 million is easily within reach – at the least, something resembling teammate Max Scherzer’s seven-year, $210 million pact.

Having foregone free agency once, is Strasburg intrigued by going to the highest bidder? Will his comfort level in D.C. be superseded by a chance at a lifetime contract closer to family?

And will the Nationals go to any length to retain him?

We may not get all the answers next week, but a Washington club that also needs an up-down response from fellow Scott Boras client Anthony Rendon may soon be inspired to come forth with a best-and-final-ish offer, as it did with Harper.

How desperate are the Dodgers and Yankees?

In an alternate universe, Clayton Kershaw doesn’t pitch a fateful eighth inning, Adam Ottavino isn’t called upon to give up a key home run and Fox is still basking in the mega-ratings of a Dodgers-Yankees World Series.

And at least one of those teams would have snapped a championship drought each considers unacceptable.

Instead, the Nationals are champs and the Dodgers (Last title: 1988) and Yankees (2009) are left wondering whether dipping under myriad luxury-tax thresholds isn’t as thrilling as hoisting the Commissioner’s Trophy.

Now, how far are they willing to go to grab it?

Both franchises are flush with cash, talent, flexibility and creative front offices that can pivot quickly from one scenario to the next – and already have 100-win foundations from which to build.

Sure, the Dodgers would be happy to open 2020 with Justin Turner as their starting third baseman, and they’ll almost certainly win an eighth consecutive NL West title regardless of what they do. But the specter of adding Rendon for the long term or Josh Donaldson as a mid-range solution while trading Turner or moving him to second base is titillating. So, too, is adding a power arm like Cole or Strasburg as Kershaw continues his gentle transformation into his golden years.

The Nationals badly exposed the Dodgers’ need for more swing-and-miss from any pitcher not named Walker Buehler, and now they have two rotation vacancies with Hyun-jin Ryu and Rich Hill reaching free agency. The Dodgers opted for a higher-value, shorter-term strike a year ago with Harper, who rebuffed them for a $330 million deal with Philadelphia.

Now, another year has ticked off the calendar and their need for pitching is far more acute and specific than a luxury buy like Harper. Perhaps the time has come for a little irrationality from Chavez Ravine.

The Yankees can relate – they refused a sixth year for lefty Patrick Corbin last year and it may have cost them a championship shot. GM Brian Cashman isn’t wrong when he says a 103-win team doesn’t need an overhaul. But they’ve also failed to win a pennant since the famous splurge of December 2008 that netted CC Sabathia, Mark Teixeira and A.J. Burnett.

Perhaps a bi-coastal bidding war for the ace both clubs need will be sparked in San Diego.

Who’s ready to quit tanking?

Call it tanking, or rebuilding, or retreating, but suffice to say, more than half of major league teams have done it in the past five years.

Now, more than a few franchises seem poised to pivot toward competing again.

The Padres (Eric Hosmer, Manny Machado) and Phillies (Harper, McCutchen, now Wheeler) joined the fray in earnest the past two years. The Reds dealt for Trevor Bauer in July, signed Moustakas this month and certainly aren’t done.

Who’s going to join them?

The smart money is on the Rangers, who are opening a new ballpark, already gave pitcher Kyle Gibson a three-year deal and would love to lure Houston native Rendon to “North Texas.” Yet there will be others.

While the game’s financial state leaves little incentive for owners to try and win, several franchises nonetheless will find their windows of contention close to opening or, perhaps, realize relevance isn’t a bad thing both at the gate and in TV ratings.

So, while their fans may be numb to their club’s inaction, don’t be stunned to see the Blue Jays, Pirates, Mariners and Giants try to buy a little goodwill, if not a pennant.

Will franchise icons land on the block?

Mookie Betts is just 27 years old, a mere 13 months removed from winning both a World Series championship and an AL MVP award. Yet in the hyper-efficient modern reality of the industry, even a team like the Boston Red Sox won’t hesitate too long before dealing a free-agent-to-be in the service of sustainability.

Betts and the Red Sox have never gained traction on a long-term deal, but his fate seemed particularly sealed with the dismissal of win-now-always GM Dave Dombrowski and hiring of Rays expat Chaim Bloom.

Efficiency and mega-contracts for franchise players rarely intersect.

What’s more, several teams seem to have identified “micro-windows” where trading for a rental such as Betts may look more palatable than usual. The Reds, Mets, Braves, Athletics, Twins – all fit the mold of typically unlikely trade partners who might be motivated to take a shot in 2020.

It’s also getting late early for plenty of other young stars, most notably Cubs third baseman Kris Bryant, now just two years removed from free agency and with a grievance pending against the club that suppressed his service time as a rookie.

Players like Betts and Bryant are special cases, what with the hits a club would take from its fan base to move them. It would take quite the lightning strike for such a maneuver to come together at the Winter Meetings.

Then again, things are already moving quickly, a fact for which all parties are grateful.