Biggest free-agent deals in Winter Meetings history

Biggest free-agent deals in Winter Meetings history

Above the constant hum of rumors pulsing through the Winter Meetings occasionally arises a loud statement in the form of a franchise-altering agreement with a free agent, a bold move commanding the attention of the baseball world.

When representatives from all 30 teams convene starting on Monday, a batch of sluggers -- Jose Bautista, Edwin Encarnacion and Mark Trumbo -- along with stellar closers -- Aroldis Chapman and Kenley Jansen -- give free agency plenty of room at the bargaining table this time around. and MLB Network will have wall-to-wall coverage of the 2016 Winter Meetings from the Gaylord National Resort & Convention Center outside Washington. Fans can watch live streaming of all news conferences and manager availability on, including the Rule 5 Draft on Thursday at 9 a.m. ET.

Setting tone for Winter Meetings

Obviously, groundwork will be laid outside D.C. for deals that come later, and many big past deals have been consummated on the doorstep of the meetings -- last year's megadeal for Zack Greinke with the D-backs, for instance. But free agency has delivered plenty of action at the annual convention over the years.

Here's a look at times when free agency had the biggest impact on the Winter Meetings:

1980: Winfield narrows it down
When Dave Winfield signed the first blockbuster deal ever for a free agent, agreeing to a record-shattering 10-year, $23 million contract with the Yankees, he signed on the dotted line the day after the Winter Meetings were held in Dallas.

For the Mets, those Winter Meetings were the last chance to trade for a player who could complement Winfield, reportedly targeting Fred Lynn of the Red Sox, among others. But the efforts of Mets GM Frank Cashen came up short, and despite extending a 10-year, $12 million offer, the Mets finished out of the running for Winfield, who had insisted on more lineup protection. Cashen was quoted as saying it would be nice to have both Lynn and Winfield, "But who would pay the ushers?"

Five years earlier, in the winter of 1975, Jim "Catfish" Hunter signed with the Yankees on New Year's Eve to usher in the free-agency era. But the Winfield signing really set off the age of bigger and bigger contracts, and it had a brush with the Winter Meetings thanks to the Mets' 11th-hour trade efforts.

1988: Ryan Express to Arlington
At age 41, Nolan Ryan was already the game's all-time strikeout king and had five no-hitters under his belt before signing a one-year, $1.5 million deal with the Rangers at the Winter Meetings in Atlanta. Ryan would go on to pitch five more seasons and deliver two more no-hitters for the Rangers. He wound up with 5,714 strikeouts after retiring at age 46, ultimately becoming a club president with the team.

1992: Two record contracts
The meetings in Louisville, Ky., in '92 featured an avalanche of signings, with some 30-plus agreements hammered out at the session alone. But none were bigger than the Giants getting Barry Bonds to play for his hometown team and the Braves grabbing the best pitcher in the game by signing Greg Maddux.

Shortly after a move to Tampa, Fla., was scuttled and a local group of investors stepped up to keep the team in San Francisco, the Giants went all in to get Bonds, signing him to a six-year, $43 million deal to make him the game's highest-paid player. Bonds went on to a record-setting career that included home run No. 756 at AT&T Park, the ballpark that was merely a pipe dream at that time.

Bonds' 756th career homer

At those same meetings, Maddux left the Cubs behind after his first Cy Young Award and became the highest-paid pitcher in the game with a five-year, $28 million deal. He followed up the payday with three more consecutive Cy Youngs for the Braves en route to a Hall of Fame career.

1998: The $100M barrier
After one season in San Diego and a trip to the World Series, Kevin Brown became the first to break the $100 million barrier for a contract's total value during the Winter Meetings in Nashville, Tenn., when he signed a seven-year, $105 million deal with the Dodgers. Brown was traded to the Yankees five years and one day later, after 58 wins and a 2.38 ERA in 137 appearances with the Dodgers, but none in the postseason.

2000: Big deal in Big D
When it comes to shaking things up at the Winter Meetings, nothing compares to the startling crescendo the Rangers delivered to finish off the 2000 meetings in Dallas. The 10-year, $252 million deal for shortstop Alex Rodriguez, then 25 and already considered the game's best all-around player, was as big a news item as has ever been dropped on the Winter Meetings docket.

Rodriguez won one Most Valuable Player Award in three years in Texas before being traded to the Yankees. He won a World Series ring in 2009, served a 162-game suspension for using performance-enhancing substances, and completed his career in 2016 with 3,115 hits and 696 home runs.

2008: Yankees fly, land CC
Most deals at the Winter Meetings are consummated in a team's suite at the headquarters hotel, or perhaps a restaurant. But Yankees general manager Brian Cashman went so far as to hop on a plane from Las Vegas to the San Francisco Bay Area to close a deal for CC Sabathia in a Winter Meetings coup. The trip landed Sabathia to the tune of a seven-year, $161 million deal -- then the largest ever for a pitcher.

"I told them I would be more than willing to fly from Vegas to continue our efforts by meeting in California," Cashman said. "They welcomed that idea, so I took advantage of it and bolted."

2010: Outfielders go big
Jayson Werth and Carl Crawford were both All-Star performers heading into free agency, but the contracts they found at the Winter Meetings in Orlando, Fla., were shockers. Werth signed a seven-year, $126 million deal with the Nationals at the outset of the meetings, and Crawford followed with an eye-boggling seven-year, $142 million contract with the Red Sox. While Werth has been part of three Nats playoff teams, Crawford was traded to the Dodgers in 2012 and then released last June.

2011: Halo, Albert
The Marlins had made all the news at the meetings held in Dallas in '11, signing closer Heath Bell, veteran starter Mark Buehrle and, finally, shortstop Jose Reyes, awarding him a six-year, $106 million deal to finish off a trifecta of free agents.

But the Angels swooped in and stole the Marlins' thunder as teams were headed out the door with a colossal 10-year, $240 million deal for Albert Pujols. The announcement of that mega-deal was combined with the signing of left-hander C.J. Wilson to a five-year, $77.5 million contract. Much like the A-Rod deal 11 years earlier, this was a last-minute salvo that shook the baseball world.

2014: Building a champion
The Cubs have used the last two Winter Meetings to make free-agent inroads toward their historic World Series victory. Last year, the Cubs did quite well to pick up Ben Zobrist and John Lackey as free agents, but they really hit the jackpot the year before, winning the sweepstakes for left-hander Jon Lester.

Lester signs with Cubs

His former team, the Red Sox, and the Giants were among the suitors for Lester, but he landed in Chicago with a six-year, $155 million contract that is the largest in Cubs franchise history and among the top annual salaries of all time.

Suffice it to say things are working out fine with this foray into free agency, one of several to make noise at baseball's Winter Meetings.

John Schlegel is a national reporter for You can follow him on Twitter @JohnSchlegelMLB. This story was not subject to the approval of Major League Baseball or its clubs.