Rays' top 5 Winter Meetings transactions

December 7th, 2020

ST. PETERSBURG -- In almost every way, 2020 has been a year of adjusting to the circumstances. Due to the coronavirus pandemic, the annual Major League Baseball Winter Meetings will be held virtually this offseason.

Instead of heading to Dallas this week, the majority of the baseball world will be on Zoom, waiting on teams to be active on the free agent and trade markets. The Rays will surely be in the market for a catcher and a pair of pitchers.

While we wait on some Hot Stove action, let’s take a look at some of the big deals the Rays have pulled off during the Winter Meetings.

1) becomes a Ray
During the 1998 Winter Meetings, the then-Devil Rays made their first big free-agent splash since becoming an expansion team, signing Canseco to a one-year deal with two club options. Canseco was coming off a 46-homer season with the Blue Jays, and he carried that power during his time with the Rays. The slugger hit 34 home runs with Tampa Bay during the ‘99 season, making his first All-Star team since ‘92 in the process.

2) Charlie Freakin’ Morton
After winning 90 games in 2018, the Rays entered the Winter Meetings in Las Vegas looking for a veteran starting pitcher to pair up with young stars and . That description fit perfectly, and the two sides were able to come to an agreement on a two-year, $30 million deal. The $15 million annual salary became the highest for a pitcher in Rays history, and Morton made sure he was worth every penny, winning three win-or-go-home games for the club in the postseason. Morton went 18-8 with a career-low 1.135 WHIP with the Rays, but he signed a one-year, $15 million deal with the Braves this offseason.

3) Party like it’s 1999
We’ll cheat a little bit here and list two moves that took place during the 1999 Winter Meetings in Anaheim. The Rays, who were desperately looking to bolster their lineup after two tough seasons, acquired from the Rockies in exchange for pitcher Rolando Arrojo and infielder Aaron Ledesma. Tampa Bay also came to an agreement with Greg Vaughn on a four-year, $34 million deal.

Castilla didn’t pan out for the Rays, hitting just eight homers in 109 games. Vaughn, on the other hand, knocked 60 home runs in three seasons with Tampa Bay, making the All-Star team in 2001.

4) The trade
This is one deal Rays fans will probably never forget. During the 2012 Winter Meetings in Nashville, the Rays came to terms with the Royals on a deal that would send Shields to Kansas City, ending his incredibly successful tenure in Tampa Bay.

Despite the emotional pain that came with dealing Shields away, Rays fans probably remember it in a positive light as it landed the organization , , and .

Montgomery didn’t find success until he was a key member of the Cubs' World Series club, but Odorizzi was a constant in the rotation for a couple of years and Myers took home the American League Rookie of the Year Award in 2013. Unfortunately for Myers and the Rays, the outfielder struggled in ‘14 and was then traded to the Padres.

5) Rays answer back with
All the Hot Stove talk during the 2017 Winter Meetings surrounded the trade between the Yankees and Marlins that sent Giancarlo Stanton to the Bronx. During all that, however, the Rays quietly dealt with the A’s, acquiring Wendle from Oakland. The move was hardly a response to what the Yankees had just done, but since the two trades went down, only one of those two players has appeared in a World Series game.

Honorable mention
The Rays pulled off a somewhat under-the-radar trade with the Braves in 2009, landing for . That move proved to be a big one as Soriano led the AL in saves the following season with 45. … and his biceps were acquired during the ‘18 Winter Meetings in a three-team deal with the Tribe and the Mariners. was the notable Tampa Bay prospect sent over to Cleveland. … During the ‘04 Meetings in Anaheim, the Rays traded to the Blue Jays in exchange for a player named , who played just 13 games with the Rays and finished his career with a -3.1 bWAR. At least he’s one of the best at his current gig.