Inside story of 5 Winter Meetings blockbusters

December 8th, 2019

The Winter Meetings have long been viewed as the biggest event of baseball’s offseason, though some years have provided more fireworks than others.

Some of the game’s biggest deals – both in terms of free agency and trades – have gone down at the Meetings, so the Executive Access podcast took a closer look at a number of them in a special Winter Meetings episode.

Here are five of the transactions featured on the podcast, which is available for download now:

Rangers sign A-Rod to a biggest deal in sports history
The biggest contract in baseball history was signed at the 2000 Winter Meetings in Dallas, when Mike Hampton inked an eight-year, $121 million pact with the Rockies.

By the time everybody left Dallas, that record had been shattered.

Alex Rodriguez’s historic contract with Texas was the biggest in North American sports history at the time, doubling Kevin Garnett’s deal with the NBA’s Timberwolves. T.R. Sullivan, MLB.com’s Rangers beat reporter, was covering the club for the Fort Worth Star-Telegram at the time, breaking the story that A-Rod was going to sign with Texas.

As ESPN and other outlets reported the news, a problem arose as agent Scott Boras told Sullivan late that night that no decision had been made.

“About 1:00 in the morning, Scott Boras comes into the press room and I asked him, ‘Is it a done deal?’” Sullivan recounted. “He said, ‘Nope, that’s not true.’”

Rodriguez agreed to terms the following day, capping a week during which Texas signed A-Rod, Andres Galarraga, Ken Caminiti and Mark Petkovsek.

Sabathia signs seven-year, $161 million deal with Yankees
In December 2008, the Winter Meetings made their Las Vegas debut, sending the baseball world to the glitziest city in the world for the first time.

As executives, agents and media types roamed the Bellagio, one notable general manager departed the premises to take care of business.

“It was in Vegas, so there was a lot of noise, the bright lights,” recalled Bryan Hoch, MLB.com’s Yankees beat reporter. “Not that you got to get out of the hotel very much, but [Yankees GM] Brian Cashman did.”

Cashman snuck out of the Meetings to fly to Northern California, where he met with CC Sabathia, who was the biggest free agent on the market, both literally and figuratively.

Sabathia had met with Cashman and the Yankees twice in Vegas that week, but the GM hopped on a flight to try closing the deal like a college basketball coach looking to lock up a blue-chip recruit.

“There’s so much buildup to the Winter Meetings, where all the executives are going to be under the same roof,” Hoch said. “Not having Cashman under that roof, you knew he was off doing something and you knew it was going to be big.”

The trip paid off as the Yankees got their man.

Pujols shuns Cardinals, signs $240 million deal with Angels
When the 2011 Winter Meetings began in Dallas, it looked like the Cardinals’ primary competition for Albert Pujols would be the Florida Marlins, who were prepared to offer the three-time MVP a deal worth more than $200 million.

St. Louis was still hoping to retain Pujols – one prominent writer even reported during the Meetings that the two sides were closing in on a deal – but the Marlins were making a big push.

“It was frantic in a way that the Winter Meetings aren’t always,” said Matthew Leach, MLB.com’s NL executive editor, who was on the Cardinals beat at the time. “It was trying to get that read as to what’s real and what’s not.”

As it turned out, the Angels were certainly the real deal. They swooped in with a monster offer, securing Pujols’ services for the next decade as the slugger left St. Louis following a decade-plus of excellence.

“They had no desire to play in the end of the pool that the Angels ended up going to,” Leach said. “If you had told them at any point that that was what it would take to get a deal done, they would have said, ‘Good luck.’”

Crawford inks seven-year, $142 million deal with Red Sox
Just three years after the Red Sox had won their second World Series of the decade, Boston entered the 2010-11 offseason with some urgency.

The Red Sox had missed the postseason for the first time in four years, and the core that had led the team to the World Series championship in 2007 was getting older, while the farm system was not producing the type of talent Boston needed to replace its aging stars.

“They had to do something to cause some excitement,” said Peter Abraham, national baseball writer for the Boston Globe. “They just started going for the big-ticket items.”

Add in the fact that the Yankees had reloaded a couple years earlier with Sabathia, Mark Teixeira and A.J. Burnett, and the Red Sox felt some pressure to make big moves.

“That was at a time that the Red Sox had to counter what the Yankees did,” Abraham said. “If the Yankees had a big offseason, the Red Sox had to either counter that offseason or come back strong the following season.”

The first came before the Winter Meetings, when Boston acquired All-Star first baseman Adrián González in a trade with the Padres. As the baseball world descended upon Disney World the following week, it was clear that Carl Crawford – who had always thrived against the Red Sox during his years in Tampa Bay – was Boston’s top priority at the Meetings.

“That’s where it really stated to percolate,” Abraham said. “It became very evident that he was the guy they were focused on.”

The two sides agreed to the mega-deal, which didn’t work out as well as either had hoped. Crawford played two seasons in Boston without reaching the playoffs, then was traded to the Dodgers following the 2012 campaign.

Tigers acquire Miguel Cabrera from the Marlins
Everybody in baseball knew the Marlins were willing to trade Miguel Cabrera after the 2007 season, but his ultimate destination came as a shock to most.

“Covering the Winter Meetings with Dave Dombrowski was never boring; you were always on guard for something,” said Jason Beck, MLB.com’s longtime Tigers beat reporter. “Even going into that, Dave was downplaying things, so there was a little bit of a calm going into those Meetings.”

The Angels appeared to be the frontrunners to land Cabrera that offseason, even as the Winter Meetings began in Nashville.

“Nobody really saw the Tigers as being seriously interested,” Beck said. “And nobody saw the Tigers as being that team that would go all-in to make a deal like this.”

Yet on the second day of the Meetings, Dombrowski and the Marlins spoke for the first time about a potential Cabrera deal. Florida set its asking price, and within hours, Cabrera – and fellow Marlins All-Star Dontrelle Willis – were set to become members of the Tigers.

The price was a six-player package led by Andrew Miller and Cameron Maybin, the Tigers’ top two prospects.

“This was kind of the dividing point where they went from a team looking to win from the long term into a team looking to win now,” Beck said. “That philosophy carried them really for the next decade.”