Chicago Cubs - Winner
When Lester signed with the Cubs, we knew that they had achieved their ultimate goal of the offseason. And now, they are among the best in the National League, with a chance to make the playoffs for the first time since the 2008 postseason. Jon Lester is that type of player. He is the guy you want in a Game 7, a postseason clincher, or any other big game. No, I'm not talking about James Shields, I'm talking about Lester, who has a 2.57 ERA in the playoffs, as a two-time World Series champion.
But it isn't just Lester that makes the Cubs the winners of this Winter Meetings. They made one other move, much more strategic and a lot less prevalent, acquiring Miguel Montero from the Arizona Diamondbacks. The Cubs have needed catching, finishing second in the Russell Martin bidding, and the acquisition of Montero fits the bill. He's under team control for three more years and posted a 1.2 fWAR in 2014. The Cubs can surround Montero and Lester with their prospects and have a shot at the postseason.
Chicago White Sox - Winner
Move to the south side of Chicago, where we find our other Winter Meetings winner. The Chicago White Sox played both the free agent and trade markets well. They acquired Jeff Samardzija from the Athletics in a six-player deal and now they boast a rotation of Chris Sale, Jose Quintana, Samardzija, and Jon Danks. Samardzija makes the White Sox rotation look like a contender's rotation, and now their team looks like it could be a contender.
The White Sox also added David Robertson to their relief corps that were highly inexperienced last season. Him and Zach Duke represent their transactions of relief pitchers this offseason, which helps to evolve a White Sox bullpen that previously didn't have anyone over the age of 27 in it. Duke and Roberston add experience and talent to a now-interesting Chicago team.
Los Angeles Dodgers - Winner
Dee Gordon, Howie Kendrick, Matt Kemp, Yasmani Grandal, Andrew Heaney, Enrique Hernandez, Brandon McCarthy, and Jimmy Rollins. What do all those names have in common? They were all involved in either a trade or a signing with the Dodgers. President of Baseball Operations Andrew Friedman kempt (sorry, bad pun) himself busy during these meetings, wheeling and dealing with the Phillies, Marlins, Angels, and Padres. I'm not even sure who is on their roster anymore.
What makes the Dodgers a winner, you ask? They were able to unload one of their big-time outfielders (Kemp), while getting a young, promising catcher, something they needed, in return. They traded Dee Gordon, who posted a poor .648 OPS in the second half for Andrew Heaney, Chris Hatcher, and Austin Barnes. Heaney's career with the Dodgers didn't even last 12 hours, as they filled their hole at second base with an even better option than Gordon in Howie Kendrick, who, at 31, is among one of the better all-around second baseman in baseball. Oh yeah, they also signed Brandon McCarthy and traded for Jimmy Rollins, too. The Dodgers upgraded their outfield, catcher, shortstop, and rotation all in the matter of 24 hours.
Miami Marlins - Winner
Once the Miami Marlins signed Giancarlo Stanton to that big $325 million extension, I really wasn't sure if the Marlins thought they could be contenders, or if they just wanted to keep that gem they had in Stanton on their roster. After these Winter Meetings, I can definitely see that the former is true. They acquired Dee Gordon and Mat Latos at the Meetings, and while someone could argue that they gave up a lot, they are finally showing that they want to go all-in in 2015. Or at least have a shot at contending.
The Marlins starting eight looks like this: Christian Yelich, Marcell Ozuna, Giancarlo Stanton, Casey McGehee, Adieny Hechavarria, Dee Gordon, Garrett Jones, and Jarrod Saltalamacchia. Their rotation? Jose Fernandez, Henderson Alvarez, Mat Latos, Nathan Evoldi, and Jarred Cosart. Now you tell me, do you think the Marlins are contenders? I would say definitely. By acquiring both Gordon and Latos at the Meetings, Miami ownership proved to the baseball world that they want and are wiling to play meaningful baseball for the first time since 2003.
San Francisco Giants - Loser
I'm still confused as to what the Giants really want to accomplish in 2015. The best move for San Francisco at the Winter Meetings was getting Madison Bumgarner on the cover of Sports Illustrated after winning the Sportsman of the Year award. In all seriousness, I think you have to attribute some of the Giants' offseason success, or lack there of, to just plain old bad luck. They finished third for Lester, second for Yasmany Tomas and Pablo Sandoval. But any good Giants fan would tell you that they finished first in the most important category.
I'm still trying to understand where the Giants plan on spending the money that they were planning to give Lester, Tomas, or Sandoval. Could they go after a guy like James Shields? That would be interesting. Whatever the case, the Giants did not get better at the Winter Meetings. I guess that means San Francisco fans should just start watching the team again in 2016, the next even year.
Baltimore Orioles - Loser
The Orioles have lost Nelson Cruz, Nick Markakis, Andrew Miller, and now perhaps their general manager, Dan Duquette. It was rumored last weekend that Duquette might soon be on the move to Toronto to become the Blue Jays' CEO, but it was later reported that the Blue Jays would reconsider until after the 2015 season. Regardless, Duquette has to deal with a mess in Baltimore. Three months after winning the AL East, they lose Cruz and Markakis, two of their top performers from the season.
The Orioles usually stay relatively quiet until later into the offseason anyway, so they might be able to salvage a good piece of what they lost with mid-tier free agents. But for now, their Winter Meetings weren't good, and they need to find a plan to get back to the top of the American League East, a division where the Blue Jays and Red Sox have already gotten better this offseason.