ST. PETERSBURG -- The Rays don’t often “win the offseason” with splashy signings and headline-grabbing trades. So they are not necessarily built for the Winter Meetings, the offseason’s marquee event that has become a time for big transactions in the baseball world. But they have occasionally rocked the boat -- or made under-the-radar deals that looked brilliant with the benefit of hindsight.
Now, let’s take a look at some of the big deals the Rays have pulled off during the Winter Meetings:
1. Jose Canseco 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.
2. Uncle Charlie finds new home
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 Blake Snell and Tyler Glasnow. That description fit Charlie Morton 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 1.135 WHIP with the Rays before signing with the Braves to continue his remarkable second act.
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 Vinny Castilla from the Rockies in exchange for pitcher Rolando Arrojo and infielder Aaron Ledesma. Tampa Bay also came to an agreement with slugger 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 and made the All-Star team in 2001.
4. The James Shields trade
This is one deal Rays fans will probably never forget. During the 2012 Winter Meetings in Nashville, Tenn., 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 Mike Montgomery, Jake Odorizzi, Wil Myers and Patrick Leonard.
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. Under-the-radar hits
The 2017 Winter Meetings were dominated by talk about a deal between the Yankees and Marlins that sent Giancarlo Stanton to the Bronx, obviously overshadowing a trade between the Rays and A’s that brought Joey Wendle to Tampa Bay. But the versatile infielder Wendle wound up being a more valuable player for the Rays from 2018-21 (10.5 bWAR) than Stanton was for the Yankees from 2018-24 (9.1 bWAR). The Rays pulled off another under-the-radar trade with the Braves in 2009, landing Rafael Soriano for Jesse Chavez, and Soriano went on to lead the AL in saves the following season with 45.
Quite possibly their most impactful Winter Meetings trade was one of the most unusual and unexpected. In a three-team trade with Seattle and Cleveland during the 2018 meetings, the Rays sent away prospect Jake Bauers and wound up landing Yandy Díaz from Cleveland. Of course, Díaz went on to become one of the best hitters and most valuable players in franchise history as the Rays reached the postseason six times in the next eight years.