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Winter Meetings Promise to Revive MLB's Ongoing Drama

Even if we don't see major transactions at the Winter Meetings, plenty of intriguing drama still remains on tap.

At the 1876 winter meetings, the league expelled the New York Mutuals and Philadelphia Athletics for refusing to make their final road trip of the season. We are unlikely to get action that exciting next week in San Diego, but for the first time in a while, the winter meetings have a chance to be fun.

Not because any major free agents will sign, of course. Those days are over, mostly because both sides are trying to wait each other out. Expect this to be even worse than usual this year, because superagent Scott Boras represents seven of the top 20 free agents, including the top three, and Boras is legendary for prolonging his clients' free agency. This often works out of them: You may recall how Harper’s Bazaar, as Boras characterized the Bryce Harper sweepstakes last year, lasted into spring training. When Harper did finally sign with the Phillies on Feb. 28, though, it was for a record $330 million over 13 years. Dallas Keuchel, another Boras client, held out all the way until June 7, four days after the draft-pick compensation attached to him expired. He ended up with a pro-rated portion of $13 million for that season and is now a free agent again. Don’t expect Boras to change his strategy.

That is likely to affect the rest of the market: Minor free agents will often wait to see where the big guys land, and some teams will be reluctant to put together blockbuster trades with so much else unsettled. So if there’s no reason to hope for much baseball activity next week, what can we look forward to?


Everyone wants to talk about how to make baseball interesting. Well, this is interesting! The conversations about pace of play have become nearly as interminable as the hours between each Pedro Báez pitch. But what baseball has lacked more than action on the field is action off the field.

When is the last time this sport had a true villain? Alex Rodriguez? Well, good news: The Astros may have been cheating when they won the 2017 World Series.

Are you bored that every general manager seems to have been manufactured in the same facility? Here’s a fix: No one knows for sure how the baseball will behave next season, forcing front offices to build teams based on their best guesses.

Do you sometimes decry how few cartoonish billionaires are running teams? Wait until you hear about hedge funder Steve Cohen, who will eventually be the majority owner of the Mets, and who once agreed to buy Pablo Picasso’s Le Rêve for $139 million. Shortly before Cohen was due to take possession, the previous owner—casino magnate Steve Wynn—accidentally tore it open with his elbow and scuttled the deal. A restorer said the damage dropped the value to $85 million. Six years later, Cohen bought it for $155 million.

From a transactional standpoint, the winter meetings are mostly vestigial. GMs and agents can text one another (when they have service); they don’t need to be in hotel suites two floors apart to get things done. But they offer three days of baseball people talking to the media. This year, we have some fun questions to ask. We might get some fun answers.