Winter meetings winners and losers, starring Scott Boras and his $814M week

SAN DIEGO — Remember when the winter meetings lost their gusto? It sure seemed that way the past few years. Remember when hot-stove season was a free-agent freeze? It sure seemed that way recently too.

Well, the 2019 winter meetings have come and gone and sound the alarm because the winter meetings were back as baseball’s biggest money-spending, team-swapping bonanza.

And it was glorious.

Three days saw the top three free agents — Stephen Strasburg on Monday; Gerrit Cole on Tuesday; Anthony Rendon on Wednesday — coming off the board with huge deals and bold moves.

There were definite winners and losers, but the biggest winner of all was baseball as a whole. The offseason product needed a jolt of excitement and we got it. Here are more of my winners and losers for the 2019 meetings:


You can debate some of these winners and losers a bit, but there’s no doubt about this one: Scott Boras took the winter meetings by storm. MLB’s mega-agent rolled into town with the three biggest free agents and left with $814 million worth of contracts. That is what you call a good week. And he’s not done yet. His stable also includes Dallas Keuchel, Nicholas Castellanos and Hyun-Jin Ryu. If you add Mike Moustakas’ $64 million contract with the Reds, Boras’ total is $878 million this offseason, with $1 billion in contracts looking pretty likely.

Scott Boras clients fetched $812 million in three days at the winter meetings. (Photo by Michael Reaves/Getty Images)
Scott Boras clients fetched $812 million in three days at the winter meetings. (Michael Reaves/Getty Images)


The Yankees really had one move they needed to make and they made the biggest splash of the offseason. Gerrit Cole is coming to the Bronx. He’s getting $324 million over nine years — blowing past what anybody expected. But the Yankees weren’t playing around. In this case, being bold made them a winner.


The Dodgers didn’t *need* to walk away with one of the top free agents, but they were at least interested in Cole and Rendon and got neither. They’ve been a close-but-no-cigar team pretty much the whole decade, which has to be deflating if you’re a Dodgers fan. They’ll surely add to their pitching and lineup this offseason, but they didn’t have a big winter meetings moment. They didn’t even make Rendon an offer, reportedly.


You can make the argument that the Nationals should have pursued both Stephen Strasburg and Anthony Rendon and could have found the money to pay them both. But given the goalposts here — ownership made it clear they weren’t going to get both last week — the Nationals bringing back Strasburg is enough to get them in the win column.


The Yankees are making monster moves and the Red Sox are — wait, were the Red Sox even here? Some tough decisions are happening in Boston these days, with a regime change in the front office. Will they try to contend this year? Will they sell? There’s a lot of offseason left, but as the league was buzzing, they weren’t.


I’ll give the Angels the “win” here, but with a caveat that they still haven’t addressed their main need and that’s starting pitching. Still, getting Anthony Rendon to join Mike Trout and Shohei Ohtani sure seems like a nice move. They have Jo Adell coming to the big leagues soon too. If they get some pitching, they could really be a challenger in the AL West.


The flip side of Rendon-to-the-Angels and Cole-to-the-Yankees is life getting harder twice for the Astros. They lost one of their two aces and now Rendon is in their division, making the Angels a challenger for the throne. Oh, and they’re also embattled in the biggest MLB controversy in recent years.


The Texas Rangers want to be big players next season as they open their new stadium. Rendon was in their sights but they weren’t willing to pay the price. Now he’s in their division. The good news is the Rangers have money to spend still, and there are still players to be had.


Sports loves the idea of a free agent going back to where he was from. It’s a convenient narrative, but most of the time players just want the most money. This year, we heard a lot about Gerrit Cole in Orange County or Anthony Rendon in Texas (with the Rangers, even though he’s from Houston). Some people even floated the notion of Strasburg returning home to San Diego. None of those things happened, of course. Sorry, narrative.


Mike Oz is a writer for Yahoo Sports. Have a tip? Email him at or follow him on Twitter! Follow @mikeoz

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