Because we are both messy and judgemental, we decided to give the 2019 meetings a proper sendoff by naming four winners and four losers from the offseason’s most hectic week. Before we get to the praising and shaming, let us not that inclusion here doesn’t mean the teams listed here are guaranteed to win or lose this year; just that they had a good or bad time in San Diego. This is merely for entertainment.
If there is a downside to the week, it’s that east coast fans had to stay up a little later for their news. News of the Cole signing broke just before midnight ET on Tuesday night, and the Rendon signing was reported after 10:30 p.m. on Wednesday. Those who were in San Diego probably had their sleep schedules thrown off, too. Rest is important, people.
We covered Boras’ winter-to-date elsewhere, but the short version is that he’s likely to top billion in contracts by the time the month is over. Presuming his commission is something like five percent, that means he’ll make million off his negotiations this offseason. Pretty good.

Winner: New York Yankees

Yes, the Angels need to do more work — specifically with regards to their rotation, which could use a veteran boost or two. But adding Anthony Rendon to a roster that already includes Mike Trout and Shohei Ohtani gives Los Angeles three of the best players in the game. The Angels will also have one of the best defensive left sides of the infield in baseball, as Rendon joins shortstop Andrelton Simmons, a four-time Gold Glover. 

Loser: Houston Astros

As with the Rangers, the Dodgers failed to meet the high expectations placed upon them entering the week. They whiffed on Cole, they whiffed on Rendon (reportedly without making an offer), and they haven’t yet landed Francisco Lindor or whomever else is supposed to make everything all right in a trade.

Winner: Los Angeles Angels

The Astros didn’t do anything of note at the meetings, but they remain under league investigation (one that has already featured 60 witness interviews) for a sign-stealing scandal and lost one of their aces to the team they defeated in the ALCS. The Astros did briefly emerge as a “mystery team” for Gerrit Cole, but then saw him go to the Yankees hours later. Houston’s biggest competition for the AL pennant landed the best free-agent pitcher on Tuesday and a division rival got the best free-agent hitter on Wednesday (more on that below).

Loser: Texas Rangers

The Nationals are here because they retained Stephen Strasburg, their World Series MVP, but it doesn’t hurt that they might be the favorites to land Donaldson. Though Donaldson is a downgrade from Rendon, he’s the best alternative and would help them remain a threat to repeat as World Series champions.

Winner: Washington Nationals

With the addition of Gerrit Cole and the re-signing of Brett Gardner, you can make an argument that the Yankees have the best roster in baseball. Cole is a legit ace; a workhorse type with big-time stuff who is receptive to new information and strategies. He should front a rotation that could be one of the deepest in the game if Luis Severino, James Paxton, and Masahiro Tanaka all stay healthy. Gardner, meanwhile, gives the Yankees more much-needed outfield depth.

Loser: Los Angeles Dodgers

Major League Baseball’s Winter Meetings came to an end on Thursday. While nothing remarkable happened on getaway day — at least as of this writing — San Diego nonetheless saw each of the top three free agents come off the board on successive evenings: Stephen Strasburg on Monday, Gerrit Cole on Tuesday, and then Anthony Rendon on Wednesday.

Winner: Scott Boras

An added bonus for the Angels forking out the dough to land Rendon? It kept Rendon away from the Rangers, a division rival. The Rangers have done some good work already this winter, nabbing Kyle Gibson and Jordan Lyles to improve their rotation, but everyone expected more from them this week. With word circulating that the Rangers could already be out on Josh Donaldson, it leaves you to wonder if their new ballpark will open on a bittersweet note. There’s still plenty of time before that first game is played at Globe Life Field, but the Rangers failed to make noise in San Diego.

Loser: Sleep schedules

Now, let’s get to it.