Bold MLB Winter Meetings 2019 Predictions

With MLB Winter Meetings just hours away, trade and free agency rumours have been spreading like wild fire. Winter meetings bring out an interesting side of the MLB fan community, and there’s nothing like some insane predictions to add fuel to that fire!

Alyssa Cohen
AC Sports
7 min readDec 8, 2019

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Long time, no chat! It has been a hot minute since I wrote anything related to sports — specifically baseball, online (other than Twitter, of course). Initially, I was essentially “reporting” stories that were already official (game recaps, trade announcements, etc.), but that got boring very quickly. I have decided to bring back AC Sports and make it into what I really want to write about… ALL THINGS MLB! Whether that may be predictions, trade announcements, recapping a crazy media press conference, or anything of that sort. I hope you will enjoy this “new era” of AC Sports as we head into the 2020 MLB season (which is just 109 days away — not like anyone’s counting, though)!

MLB Winter Meetings are my absolute favourite part of the MLB offseason. Every year, I enjoy turning on channel 508 (my local MLB Network channel number), and watching all of the sports coverage straight from the hotel lobby of where the MLB Winter Meetings take place. This year, the winter meetings are being held in San Diego, California at the Hilton San Diego Bayfront. And trust me when I tell you there are no shortage of rumours during this years winter meetings! One of my favourite things to do is to try to scheme up all sorts of crazy predictions for the winter meetings, and some of them have actually come true! And even though some of these may not be super crazy, they will certainly be headline breakers if they turn into reality.

(Curtis Compton/Atlanta Journal-Constitution via AP)

Josh Donaldson re-signs with the Atlanta Braves

This is definitley one of my least adventagous predictions. After an injury haunted 2018 season, Donaldson signed a one-year $23-million contract with Atlanta for the 2019 season. Fortunatley for both him and the Braves, Donaldson returned to his usual form, and ended the season with a NL Comeback Player of the Year trophy with his name on it. Along with his fantastic numbers, Donaldson was loved within the Braves fanbase, clubhouse and front office. Signing Donaldson back would be a huge win for Atlanta, as they try to make another push to the 2020 MLB playoffs.

Stephen Strasburg re-signs with the Washington Nationals

Not only is Strasburg one of the best pitchers in all of baseball, but he also just so happens to be the reigning World Series MVP… and he did that all in the final year of his recently expired contract. I doubt there are any teams that would not benefit from adding Strasburg to their 2020 roster, but of course he is looking to get paid excellently this off-season. In my mind, the Nationals are still the best team for him. Obviously the whole city loves him, but the whole organization is constantly praising his character as well. And despite opting out of his contract, there is still a sense of wanting to return to the only team he has ever played for. The main problem with the Nationals, however, is that they simply cannot afford to re-sign both Anthony Rendon and Stephen Strasburg, two of their top superstars. Should they re-sign a top of the rotation starting pitcher, or re-sign a reliable 3B that put up career-best numbers in their championship year?

Frank Franklin II/Associated Press

Gerrit Cole signs with a team not named the New York Yankees

Yes, I know what you are all thinking. “Alyssa, didn’t you just hear how much the Yankees have reportedly offered Cole?” Yes, yes I have. HOWEVER, I think there is still a chance Cole signs with another team this off-season. Gerrit Cole is the best starting pitcher on the free agency market this year, there is absolutley no doubt about it. And while the Yankees have the money to spend (or rather, splurg) on Cole, I still believe that there are many other teams on the cusp of signing him, that still have a decently good chance to do so.

Boston Red Sox trade David Price

In 2015, David Price was my favourite pitcher and is still on my top-favourite MLB players of all time list. While I was heart broken to see him leave Toronto to go play for the stinky Red Sox (even though TO didn’t even offer him a contract… *insert mad/angry/sad face here*), I was so ecstatic to see him push through his playoff struggles and lead Boston to their 2018 World Series championship. Currently, David Price is coming off of a mediocre 2019 season. It was up to him to help push the Red Sox back to the top of the AL East standings, however, they fell quite short this past season. This off-season, the Red Sox are looking to significantly reduce their payroll, and are trying to ship off some veteran players with large contracts in exchange for young talent. That is easier said than done, especially in the case of David Price. While Price is still a top pitcher, he is the highest paid pitcher of all time and his contract has him signed until 2022. He is still owed over $90-million, which not many teams are looking to spend on a 34-year-old pitcher (although I cannot forsee a scenario in which the Red Sox would not have to a good chunk of his remaining salary). I, for one, would love to see him back in Toronto, but I know many of you would (rightfully) disagree.

Brace Hemmelgarn/Minnesota Twins/Getty Images

Cleveland Indians trade Fransisco Lindor to the Los Angeles Dodgers

Francisco Lindor trade rumours have been on fire for the past few weeks. Even though I still don’t think it makes sense for Cleveland to trade the face of their franchise, I do believe there is a stellar market for him that may decrease over the coming years. The only way Cleveland would even consider trading Lindor would be if the return for him was unbelievably groundbreaking. The Dodgers would be a phenomenal suitor for Lindor, as they are believed to be willing to give up their top prospect SS/2B Gavin Lux, along with some pitching and an outfielder. As Jim Bowden shared when discussing the potential Lindor to LAD trade;

Lindor is one of the best overall players in baseball; he can hit for average and power and is an elite defender. Lindor has a Magic Johnson-caliber smile and would look great on LA billboards alongside Cody Bellinger. The price to get him would be steep, but worth it — especially since the Dodgers have the resources to sign him long-term.

Brian Davidson/Getty Images

Toronto Blue Jays trade Ken Giles

I couldn’t write an entire winter meetings predictions post and not include a big Blue Jays prediction! Unfortunatley, I think the Blue Jays will trade closer Ken Giles. Giles was Toronto’s best player last year by far, although it wasn’t that hard to do so, as many highly touted Blue Jays prospects underperformed. With playoff contention looming in the distant future for the Blue Jays, it makes sense to trade Giles at his current high value. Teams like the St. Louis Cardinals and Texas Rangers would benefit from trading for one of the best closers in the game, and could afford to trade some high prospects or young talent in exchange for him.

Nick Wass/Associated Press

Kris Bryant traded to the Atlanta Braves

If the Braves fail to re-sign Josh Donaldson, it makes perfect since for them to try their hardest to aquire Chicago Cubs 3B Kris Bryant. Bryant has been one of the best third basemen in the game since 2015, his rookie season. Without Donaldson, Atlanta will have a gap to fill at 3B, and they will be in need of a strong power bat. Atlanta could afford to send Chicago a few of their many young pitching prospects, along with their top centrefield prospect, Cristian Pache. Pache is already in AAA and will likely be promoted to the big leagues during the middle of the 2020 season.

The 2019 Winter Meetings are expected to be filled with some blockbuster trades and free agent signings, and I for one hope it exceeds all of our expectations. Do you disagree with any of my bold MLB winter meeting predictions? What are some of your early predictions with the winter meetings just hours away? Tweet me @aalyssacohen, and I’d be happy to discuss with you!

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