Will Cole, Strasberg or Rendon Join The List Of Biggest Winter Meetings Signings?

It’s that time of year again. A time when all the general managers from around Major League Baseball congregate together wearing fun Hawaiian shirts in some warm locale (this year it’s San Diego,CA) to do some wheelin’ and dealin’ in hopes of signing that one player or two that turns your pretender into a contender. There’s a lot of standing around the hotel lobby, lots of walking around, and sometimes even a deal or two gets done, be it via trade or free agent signing. This year will be no different as teams with deep pockets are looking to land big fish like Gerrit Cole, Anthony Rendon, and Stephen Strasburg, if they’re lucky. All three will draw huge interest, but it remains to be seen where they will end up.

Before we get there though, let’s take a walk down memory lane and take a look at some of the biggest winter meetings signings ever.

1965: Frankie Rob Goes To The O’s

Let’s take a ride in the way-back machine for this one. This is arguably one of the biggest acquisitions ever in that it changed the course of an entire franchise for a decade, and even the course of baseball history. Frank Robinson was traded from the Cincinnati Reds to the Baltimore Orioles for Jack Baldschun, Milt Pappas, and Dick Simpson, three guys who were barely ever heard from again. Robinson would go on to win two World Series with the O’s and the ‘66 American League MVP. More importantly, he went from great player to icon, and forever holds a place in the heart of every Baltimore Orioles fan, young and old.

1984: The Bronx Bombers Sign Rickey

In 1984 the Yankees did what they always did, and still do, and that is make a huge splash at the winter meetings. They sent five(!) players to the Oakland A’s in a trade for future Hall of Famer Rickey Henderson. His subsequent five years in New York didn’t yield any championships, but it wasn’t his fault. Henderson swiped 326 bases and recorded 663 hits in those five seasons; only Derek Jeter stole more bases as a Yankee (358), but he did so in 2,151 more games!

1990: The Padres-Blue Jays Blockbuster

This one was huge mainly because of the equality of the players involved; at the time it couldn’t have been more fair, a completely even swap. The Toronto Blue Jays traded Fred McGriff and Tony Fernandez to the Padres for Joe Carter and Robby Alomar. Hindsight says the Blue Jays won the trade as Carter and Alomar led them to their only two World Series championships, while the Padres have still never won any. But McGriff and Fernandez went on to play well with San Diego so that was about as fair a two-for-two trade could’ve possibly went.

1992: Maddux and Bonds

The ‘92 MLB winter meetings had a flurry of activity, with no less than 30 acquisitions that week. These meetings would still make this list if the 5-year, $28 million (the biggest ever at the time for a pitcher) deal that Greg Maddux signed to join the Chicago Cubs was the only big signing of the week, but that was a mere appetizer. The biggest deal of these meetings was one that changed the game and would reverberate for years to come, for reasons good and bad. Thare the meetings where Barry Lamar Bonds would sign with the San Francisco Giants for $43 million over six years, chump change today but a record at the time. Bonds never got the Giants a World Series (not his fault as they were six outs away from winning one), but he did become the all-time leading home run hitter as a Giant and was solely responsible for them getting a new downtown ballpark.

2011: A St. Louis Icon Moves West

In 2011, Albert Pujols did something many thought he’d never do, and that is leave the St. Louis Cardinals. On the last day of the 2011 winter meetings, the future Hall of Famer signed a massive 10-year, $240 million contract with the Anaheim Angels. Though the Angels haven’t won a World Series with Pujols, he has hit his 500th and 600th home runs in an Angels uniform.

These are just a handful of the biggest acquisitions. There were (and will be) so many more, but these five stick out the most. All eyes will definitely be on San Diego this week to see what blockbuster moves will be in store. Stay tuned.

As the big names sign, be sure to visit Sportsbook NJ to see the latest MLB odds and put money down on the big winners, and the Sportsbook NJ blog for more MLB betting tips and articles. 

*Credit to the main photo of this article belongs to Alex Gallardo/Associated Press