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Biggest free-agent deals in Winter Meetings history

MLB.com @castrovince

The Winter Meetings are often the setting in which baseball's Hot Stove activity escalates, and they could be especially enthralling this year. The Meetings officially begin Monday at Las Vegas' Mandalay Bay Resort & Casino, and the availability of Bryce Harper and Manny Machado -- two 26-year-old free agents capable of commanding record free-agents contracts -- raises the stakes in a city known for such action.

Before we find out if the Harper and Machado markets will start to sizzle in Sin City, here's a trip down memory lane to look at the biggest free-agent deals in Winter Meetings history:

The Winter Meetings are often the setting in which baseball's Hot Stove activity escalates, and they could be especially enthralling this year. The Meetings officially begin Monday at Las Vegas' Mandalay Bay Resort & Casino, and the availability of Bryce Harper and Manny Machado -- two 26-year-old free agents capable of commanding record free-agents contracts -- raises the stakes in a city known for such action.

Before we find out if the Harper and Machado markets will start to sizzle in Sin City, here's a trip down memory lane to look at the biggest free-agent deals in Winter Meetings history:

2014: Goodbye, goat
The 2014 Cubs were a last-place team, but the arrival of Joe Maddon, maturation of Anthony Rizzo, readiness of Kris Bryant and breakout of Jake Arrieta all had the arrow pointed upward. Forgoing the offers of his former team, the Red Sox, and the defending World Series champion Giants, Jon Lester opted to reunite with Theo Epstein and join a Cubs club that, billy goat curse be damned, appeared to be on the cusp of something special. The contract announced at the Winter Meetings in San Diego was definitely special -- six years, $155 million. It was the largest in Cubs franchise history and gave Lester what was, at the time, the second-largest average annual value for a pitcher all time.

The Cubs stormed to a Wild Card spot and then the National League Championship Series in 2015. The following year, they ended a 108-year World Series title drought, with Lester providing pivotal relief in Game 7.

Video: A look at Lester's introduction to the Cubs

2012: Small deals, big dividends
The theme here is "big deal," but let's interject a reminder that it doesn't take a blockbuster to build a title team. In the 2013 season, the Red Sox reaped the rewards of two lower-profile signings that both occurred at the Winter Meetings in Nashville, Tenn. Having been recently freed from the entanglement of the Carl Crawford contract with an August waiver deal for the ages, the Red Sox went into the winter of 2012-13 interested only in short-term investments with second-tier free-agent options. At the Meetings, they came to terms on identical three-year, $39 million agreements with Shane Victorino and Mike Napoli (though the Napoli deal would ultimately be reworked because of his hip condition).

In 2013, Victorino (.801 OPS, 15 homers, 26 doubles) and Napoli (.842 OPS, 23 homers, 38 doubles) were instrumental in Boston's third World Series title in a 10-season span.

2011: Halo, Albert
Traditionally, the final day of the Winter Meetings is highlighted only by the Rule 5 Draft, which takes place as many executives are pouring out the doors and headed to the airport. But in Dallas in 2011, many people in the industry were packing up or boarding their flights when word spread that the Angels and Albert Pujols had agreed to a gigantic 10-year, $240 million contract. The deal, which came on the heels of the Halos signing C.J. Wilson to a five-year, $77.5 million deal, upended a Meetings that had been notable mainly for the Marlins' activity (signing Jose Reyes, Mark Buehrle and Heath Bell).

In the end, neither the Marlins nor the Angels got the expected return on investment from signing these stars, but Pujols has reached 500 and 600 homers and many other career milestones with the Angels.

2010: Werth the price?
On the opposite end of the timing spectrum from the Pujols deal was the Jayson Werth deal with the Nationals a year earlier. This one came to light just as folks were arriving to the Winter Meetings in Orlando, Fla. And the news that the Nats, who had lost 93 games in 2010, had inked the 31-year-old Werth to a seven-year, $126 million deal was certainly a stunner.

Whereas the seven-year, $142 million deal the Red Sox agreed to with Crawford later that week can be regarded as a total disaster, analysis of the Werth deal requires more nuance. He was never an All-Star in Washington, but the Nats do credit him with helping them mature into a division winner. He also hit the biggest home run in franchise history in the 2012 NL Division Series.

2008: Leaving Las Vegas
One of the biggest Winter Meetings deals did not actually take place at the Winter Meetings. And that's what made it so captivating.

On the second day of the 2008 Meetings at the Bellagio in Las Vegas, word spread that Yankees GM Brian Cashman was so encouraged by conversations with CC Sabathia that he had left the building and flown to the Bay Area to make his final pitch to the big left-hander. Sabathia's first inclination had been to return to his California roots, but a record-setting seven-year, $161 million deal lured him to the East Coast. The Yanks won the World Series in Sabathia's first year with the club.

2000: Big deals in Big D
If Harper and Machado both sign in Vegas, it will be a throwback, of sorts, to what went down in 2000. Prior to the 2000 Winter Meetings in Dallas, baseball had never had a player making $20 million a year. By the end of those Meetings, there were two -- Manny Ramirez and Alex Rodriguez.

Ramirez's eight-year, $160 million deal with the Red Sox and A-Rod's record-setting 10-year, $252 million deal with the Rangers were announced within 24 hours of each other. Nobody knew at the time what repercussions those two contracts would have in the game's greatest rivalry, as it would be three seasons before Rodriguez was dealt to the Yankees. But over the life of that initial 10-year contract, A-Rod won three AL MVP Awards and the 2009 World Series, while Ramirez won six straight Silver Slugger honors and two World Series in his colorful and memorable time in Boston.

1998: The $100 Million Man
The Winter Meetings have proven to be a place where teams push contractual boundaries over the years. In '98 in Nashville, the Dodgers did it with their seven-year, $105 million offer to Kevin Brown, whose single season in San Diego had resulted in a third-place finish in the NL Cy Young voting and a World Series appearance. The deal even included 12 roundtrip charter flights from Georgia to L.A. so that Brown's family could travel to watch him pitch.

This was baseball's first nine-figure deal, and, though Brown did have two seasons in which he got some down-ballot Cy Young support in L.A., it is generally regarded as the first nine-figure bust. Brown was traded to the Yankees five years and one day later, after posting a 2.83 ERA in 137 appearances for the Dodgers, none of which occurred in the postseason.

1992: Bonds yield
When the Winter Meetings came to Louisville, Ky., a free-agent derby (appropriate to the location) broke out. There were north of 30 pacts that week, including the five-year, $28 million deal that wooed future Hall of Famer Greg Maddux, who was fresh off his first of four consecutive NL Cy Young Awards, from Chicago to Atlanta with the richest pitching contract in history to that point.

That Maddux deal was pretty big, but the biggest deal at the epic '92 Meetings was signed by one Barry Lamar Bonds with the Giants. You know all about the records Bonds would go on to break during his time in San Francisco, but at the Winter Meetings the only record that mattered was the one Bonds set with a $43 million commitment spread over six years (he was even the first player to negotiate a hotel suite on the road). That paycheck might look paltry by today's blockbuster standards, but it was a huge investment at the time for a Giants team that had just survived the threat of a move to Tampa., Fla., when a local group of investors stepped up to keep the team by the Bay. The Giants would eventually get a new ballpark, where Bonds hit No. 756 in 2007.

1988: Express delivery
The Rangers really went for it at the Winter Meetings in Atlanta, making three trades in the first three days of the event, including bringing in Julio Franco and Rafael Palmeiro. But their biggest score was 41-year-old Nolan Ryan, who was already the game's all-time strikeout king and had five no-hitters under his belt. The Rangers' one-year, $1.8 million guarantee to Ryan was actually less than what he was offered by the Giants and Angels, but the deal kept him in the state of Texas after nine seasons in Houston and began the final chapter of his legendary career.

Ryan would go on to pitch five more seasons with two more no-hitters for the Rangers, though the club's Winter Meetings aggression did not lead it to October.

1980: Narrowing down the (Win)field
By the end of the 1980 season, Dave Winfield was fed up with the Padres, and the feeling was mutual. He embarked upon a free agency the likes of which the game had not yet seen -- one that would set a template for countless other blockbuster deals to come. Winfield had many suitors that winter, including both New York clubs. The Mets were the team that pushed bidding up to $1.5 million per year (a staggering sum at the time), but Winfield was leery about their lack of lineup protection.

So Mets GM Frank Cashen spent the week of the Meetings trying to make a trade for Fred Lynn and others, to no avail. Winfield's camp also had serious negotiations with the Indians that week. But one day after the Meetings wrapped, it was the Yankees who landed him with a record-shattering, 10-year, $16 million deal -- one that would grow quite contentious and lead to a major public feud between Winfield and owner George Steinbrenner because of cost-of-living escalators that actually pushed the value closer to $23 million.

Anthony Castrovince has been a reporter for MLB.com since 2004. Read his columns, listen to his podcast and follow him on Twitter at @Castrovince.