Blue Jays' Top 5 Winter Meetings deals

TORONTO -- Major League Baseball’s Winter Meetings are when we really start to look ahead to the coming season, with free-agent signings and major trades bringing rosters into focus as clubs jockey for the market’s best offerings.

The Blue Jays have made some of their biggest moves as an organization at these meetings, especially in the early 1990s as they chased their first -- and second -- World Series title. More recently, Hyun Jin Ryu’s four-year, $80 million deal in December 2019 put Toronto back on the map as a free-agent destination, and the club hopes that move will look even better as it becomes more competitive.

Considering moves the Blue Jays made at the Winter Meetings, or soon afterward as talks continued, here are the club’s best:

1. Blue Jays acquire Roberto Alomar, Joe Carter in blockbuster
Dec. 5, 1990

The incredible years that followed this deal included two World Series titles, Roberto Alomar’s rise to Hall of Fame stature and Joe Carter providing the biggest moment in Blue Jays history. With that context, this is arguably the best transaction in franchise history. At the time, though, it was a stunner that left fans divided, with Toronto sending franchise cornerstones Fred McGriff and Tony Fernandez the other way.

The front page of the Toronto Star on the morning of Dec. 6 read, “Fernandez, McGriff gone as Blue Jays clean house.” Alongside the story was a large picture of Carter and, beside him, a small headshot of Alomar.

“I’m disappointed, but it’s my job,” read a quote from Alomar underneath that photo. “At least I’ll get to see my brother [Cleveland catcher Sandy] more.”

The move was big and loud, and a break from the more conservative style that earned then-general manager Pat Gillick the nickname of “Stand Pat.” Just a few days prior to the blockbuster, Gillick and the Blue Jays had acquired outfielder Devon White from the Angels, whose elite defense in center field earned him five Gold Glove Awards in five great seasons with the club.

That handful of days in December 1990 changed the trajectory of franchise, and in the process, Gillick set a new standard for “a productive week of work.”

2. Paul Molitor signs three-year deal with the Blue Jays
Dec. 7, 1992

The Blue Jays nailed so many major moves leading up to the World Series runs of 1992 and '93, but the decision to bring in Paul Molitor to help defend their first title was one of the best.

Already one of the great hitters of his era after 15 productive seasons with the Brewers, the Blue Jays added the 36-year-old Molitor to round out their offense. And that’s exactly what he did, hitting .332 with a .911 OPS in 1993.

After Molitor tore the cover off the ball in the American League Championship Series against the White Sox, he put up a Fall Classic performance for the ages against the Phillies. Molitor went 12-for-24 (.500) with two home runs, two doubles and two triples -- good for a 1.571 OPS -- and won Most Valuable Player honors. The Hall of Famer spent just three seasons with Toronto, but it’s one of the finest moves the club has made.

3. Blue Jays land The Rocket
Dec. 13, 1996

In the 1996 offseason, the Blue Jays shocked baseball by signing Roger Clemens to a four-year, $31.1 million contract -- at the time the largest deal ever handed to a pitcher, and the biggest contract in club history.

The Blue Jays had pursued Clemens throughout the offseason, but it was expected that he would land elsewhere. Even Toronto's players were caught off guard.

“Gordie [Ash] called me yesterday morning,” Carter told the Toronto Star on Dec. 14. “I was shocked. I’d been following it. I thought it had come down to Boston or New York. I didn’t think we had a chance. Looks like Christmas came early.”

Blue Jays fans have rarely claimed Clemens as one of their own, and his two seasons in Toronto are often an afterthought, but he was absolutely dominant. Clemens won the AL Cy Young Award both years, pitching to a combined 2.33 ERA with 563 strikeouts over 498 2/3 innings.

Granted, the club didn't make the playoffs in either year, but with Clemens on the mound and Carlos Delgado at the dish, there was always something worth watching. Prior to the 1999 season, the Blue Jays dealt Clemens to the Yankees for Homer Bush, Graeme Lloyd and David Wells.

4. Dave Winfield added for World Series run
Dec. 19, 1991

Shortly after signing Jack Morris that offseason, the Blue Jays locked up future Hall of Famer Dave Winfield, whose big bat was just what the lineup needed to put it over the top in 1992. Then 40 years old, Winfield hit .290 with 26 home runs, 108 RBIs and an OPS of .867, finally earning the World Series ring that had eluded him.

These moves marked another shift in philosophy for the Blue Jays who, up until that point, had done most of their work through development or trades. Suddenly, they were throwing dollar signs behind their pursuit of a title -- and it worked.

5. Blue Jays find their first 20-game winner in Morris
Dec. 18, 1991

“At last, Blue Jays have a playoff starter,” read a headline in the Toronto Star on Dec. 19, 1991. That’s exactly why Toronto brought in Jack Morris, then 37, after he had won World Series rings with both the Tigers and Twins. It was a massive deal at the time, too, paying Morris $10.85 million over two seasons after a heavy pursuit.

“The deciding factor?” Morris told The Star at the time. “The smooth talk of [team president and CEO] Paul Beeston. He’s a charmer, all right.”

Morris became the club’s first 20-game winner, going 21-6 in his first season. His numbers wouldn’t be viewed nearly as favorably by today’s standards, and Morris’ postseason performance wasn’t pretty, but this was yet another timely move by the Blue Jays, who have a long history of big surprises.