What to watch at baseball’s winter meetings: Trea Turner’s timeline, Phillies’ pitching search

Three years ago, when the baseball world last gathered in person for the winter meetings, free agents Stephen Strasburg, Gerrit Cole, and Anthony Rendon signed contracts on successive days for a total of $814 million.

Could the next three days produce a similar spending spree?

Some within the sport think so, perhaps even with the Phillies at the center of the action.

» READ MORE: When will Bryce Harper play again for the Phillies? These two cases offer some clues.

The market has mostly moved slowly so far, as executives and agents size up one another like boxers in the middle of a ring. But with the industry coming together at the Manchester Grand Hyatt in San Diego — coincidentally, the site of the most recent winter meetings in 2019— it’s bound to spur movement on both the free-agent and trade fronts.

It already has. The Texas Rangers made a preemptive strike Friday night, signing Jacob deGrom to a five-year contract reportedly worth $185 million. Can a Justin Verlander deal, maybe with the New York Mets, be far behind?

The Phillies have a long, but specific, list of needs. Chief among them: a shortstop. Trea Turner, Xander Bogaerts, Carlos Correa, and Dansby Swanson are available in free agency, and although at least eight — and perhaps as many as a dozen — teams are shopping for a shortstop, the Phillies have both the money and motivation to land one of them.

» READ MORE: Phillies offseason: Key dates, trade talk, signings, analysis, and more

Beyond that, they must replace the 411 innings thrown last season by Kyle Gibson, Zach Eflin, Noah Syndergaard, Corey Knebel, Brad Hand, and David Robertson. Early indications are that the pitching market will feature few discounts. Eflin, for instance, agreed Thursday to a three-year, $40 million contract with the Tampa Bay Rays even though he has topped 130 innings in a season only once in his career.

It figures to be a busy week, then, for Phillies president of baseball operations Dave Dombrowski and his band of executives. Here are a few of the more pertinent questions heading into the meetings, which get underway Monday:

The guess here is Aaron Judge for two simple reasons: There’s only one player like him, and his market appears relatively specific.

Unlike the shortstop quartet, Judge is unrivaled among free-agent sluggers after a 62-homer season and an MVP landslide. But if the 6-foot-7 outfielder doesn’t return to the Yankees, only the Giants are reportedly in the mix for a deal that’s expected to top $300 million. (Never count out the Dodgers, but likely only on a shorter-term, high-annual-salary arrangement.)

» READ MORE: You want to trade Rhys Hoskins? Why it wouldn’t be easy or wise for the Phillies.

It’s possible Judge will sign this week, and if that happens, the rest of the market should move quickly. If the Giants don’t get Judge, they could allocate big money to a shortstop. If the Yankees miss out, they could pivot to Verlander.

And then things will really start to shake loose.

Turner counts Bryce Harper among his close friends. He had his two best seasons in Washington with hitting coach Kevin Long, who recently signed a two-year extension with the Phillies. Turner, a native Floridian, is believed to prefer playing on the East Coast. His wife is from New Jersey.

It makes sense, then, that the Phillies are widely considered the favorite to land the 29-year-old shortstop.

But as one agent joked this week, “31 teams” are interested in Turner, so the Phillies have competition.

» READ MORE: What if the Phillies whiff on a shortstop? Contingency plans to improve the roster.

None of the shortstops may be especially eager to define the market for the others. But someone has to sign first. And Dombrowski doesn’t usually dawdle when he pinpoints a specific need. When he ran the Red Sox, he targeted top-of-the-rotation pitching and acquired David Price and Chris Sale in back-to-back Decembers in 2016 and 2017.

If the Phillies believe Turner is their man, they could strike soon. But if they’re just as keen on, say, Bogaerts, who played for Dombrowski in Boston, it may be a slower process.

With Zack Wheeler, Aaron Nola, and Ranger Suárez, the Phillies like the top of the rotation. Dombrowski said they hope a “youngster” seizes the fifth-starter spot. He named Bailey Falter and Cristopher Sánchez as candidates, with 19-year-old top prospect Andrew Painter looming and touted right-handers Griff McGarry and Mick Abel not far behind.

But that leaves an opening for an experienced mid-rotation starter.

Eflin fits the description, but there have long been questions about his durability as a starter. At the rate he will be paid by the Rays — $13.3 million per year, as calculated for luxury-tax purposes — or slightly more, the Phillies are looking for innings and reliability.

» READ MORE: Longtime Phillies pitcher Zach Eflin agrees to join the Tampa Bay Rays

The Phillies were always expected to move on from Gibson, who agreed Saturday to a one-year deal with the Baltimore Orioles. But before his dreadful September, he had a 4.08 ERA in 139 innings, league-average bulk that underscores what the Phillies must now replace.

José Quintana was a Phillies trade target at the deadline, but the 33-year-old lefty went to St. Louis instead and boosted his value with a 2.01 ERA in 12 starts down the stretch. He’s generating strong interest now in free agency, according to a source.

Dombrowski could seek a reunion with Nathan Eovaldi, a favorite from his 2018 World Series championship team with the Red Sox. But Eovaldi received a qualifying offer from Boston, which ties him to draft-pick compensation.

» READ MORE: Four pitching targets who could offer some value to the Phillies

Here’s a name to remember: Jameson Taillon. The 31-year-old right-hander represents an intriguing option because of his upside.

Like Wheeler, Taillon struggled with injuries early in his career. But in the last two years with the Yankees, the former No. 2 overall pick had a 4.08 ERA, 291 strikeouts, and a league-average 100 ERA+ in 321⅔ innings over 61 starts. Wheeler’s last two years before becoming a free agent: 3.65 ERA, 374 strikeouts, 107 ERA+, 377⅔ innings, 61 starts.