Each team's biggest Winter Meetings move

The Winter Meetings are the height of the MLB offseason, becoming synonymous with blockbuster trades and big signings as star free agents, player representatives and team executives come together in one location.

With this year's Meetings scheduled for Monday-Thursday in Nashville, Tenn., here's a look back at the biggest Winter Meetings transaction in each team's history.

AL EAST

Blue Jays: Toronto lands Alomar, Carter in 1990 blockbuster

Blue Jays acquired: Roberto Alomar, Joe Carter
Padres acquired: Tony Fernandez, Fred McGriff

Looking back, this is arguably the best transaction in Blue Jays history, bringing in a future Hall of Famer and the man who authored the club’s most iconic moment, en route to back-to-back World Series titles in 1992 and '93. At the time, though, this trade was a stunner that divided Blue Jays fans, with Toronto sending fan favorites and franchise cornerstones McGriff and Fernandez back the other way. This began a string of timely moves that the Blue Jays made through the early '90s to first build, then complement, those World Series teams. None was bigger than the addition of Alomar and Carter, though, as then-GM Pat Gillick shed his “Stand Pat” nickname and he was rewarded for it.

Orioles: Robinson comes to Baltimore

O's acquired: Frank Robinson
Reds acquired: Milt Pappas, Jack Baldschun, Dick Simpson

More than five decades later, the deal that sent Robinson from Cincinnati to Baltimore during the 1965 Winter Meetings remains one of the most lopsided in baseball history. The Orioles didn’t mind how it worked out, though. Scorned by Reds owner Bill DeWitt’s comments that Robinson was “an old 30” prior to the trade, Robinson responded with the best stretch of his Hall of Fame career upon arriving in Baltimore. He earned the 1966 AL Triple Crown and MVP Award, led the O’s to a World Series title that year and then another in '70. The trade is considered former O’s GM Lee MacPhail’s parting gift to Baltimore and a turning point in the history of the Orioles franchise.

Rays: José Canseco becomes a Ray

During the 1998 Winter Meetings, the then-Devil Rays made their first big free-agent splash since joining the league, signing Canseco to a one-year deal with a pair of club options. Canseco was coming off a 46-homer season with the Blue Jays in 1998, and he carried that power into his time with the Rays. The slugger hit 34 home runs with Tampa Bay during the ‘99 season and made his first All-Star team since ‘92 in the process.

Red Sox: Ramirez signs monster deal

After competing against Manny Ramirez three times in the AL Division Series in the mid-to-late 1990s, the Red Sox went out and signed the star run producer, who would pay major dividends during his time in Boston. Ramirez, who signed an eight-year, $160 million deal on Dec. 19, 2000, joined forces with David Ortiz as one of the best middle-of-the-order duos in history as the Red Sox won the World Series in '04 and ‘07. Ramirez played 1,083 games for Boston, slashing .312/.411/.588 to go with 274 homers and 868 RBIs. While Ramirez’s various quirks always had people talking about “Manny being Manny," that shouldn’t overshadow his consistent excellence in the batter's box.

Yankees: Soto comes to the Bronx

Yankees acquired: Juan Soto, Trent Grisham
Padres acquired: Michael King, Drew Thorpe, Jhony Brito, Randy Vásquez, and Kyle Higashioka

After weeks of the Yankees and Padres going back and forth, the two clubs agreed on a trade that sent the 25-year-old Soto to the Bronx. Set to make over $30 million in his final year under contract before hitting free agency, the Padres opted to trade their superstar to rebuild their future rotation. For the Yankees, Soto represented the latest historically great hitter to don the pinstripes in New York. Unlike previous trades in Yankees history, however, Soto was something like a unicorn given his availability as an all-time great hitter smack in the middle of his prime. When the Yankees acquired him, Soto held a top-10 OPS+ (157) in the expansion era (since 1961, min. 3,000 plate appearances), tied with Hall of Famer Hank Aaron and just behind names such as Frank Robinson and his new teammate, Aaron Judge. With a Judge-Soto duo for the ‘24 season, the Yankees paired one of the best combos of hitters in baseball history.

AL CENTRAL

Guardians: Alomar, Baerga in; Carter out

Guardians acquired: Sandy Alomar, Carlos Baerga, Chris James
Padres acquired: Joe Carter

It was the trade that laid the groundwork for the Cleveland's magical 1990s teams. The franchise-defining trade that sent Carter to the Padres brought in both Alomar and Baerga -- two critical pillars in the foundation of those '90s clubs. General manager Hank Peters had Alomar locked into the trade, and was eventually able to convince San Diego to include Baerga in the deal during the 1989 Winter Meetings in Nashville. The deal worked out quite well for Cleveland. Alomar won the '90 AL Rookie of the Year Award in the first season of an 11-year career with the club, during which he hit .277 with a .734 OPS, 92 homers and 453 RBIs in 985 games. Baerga was a 21-year-old utility player who ultimately hit .299 with a .783 OPS while making four All-Star appearances and winning two Silver Slugger Awards in his eight seasons with Cleveland.

Royals: The Wil Myers blockbuster

Royals acquired: James Shields, Wade Davis, Elliot Johnson
Rays acquired: Wil Myers, Patrick Leonard, Mike Montgomery, Jake Odorizzi

This 2012 deal by general manager Dayton Moore and his staff will go down in Royals folklore as the trade that ultimately pushed Kansas City back into relevance, eventually leading to back-to-back World Series appearances in '14 and '15, the latter of which ended in a championship. Myers, an outfielder, was arguably Kansas City’s top prospect, and columnists and bloggers shrieked in horror at the notion of trading him. But Moore was adamant that it was time the Royals turned the corner from rebuilding to winning, and Shields was a huge influence in the clubhouse and on the field during that transition. Shields helped the Royals reach the '14 World Series. Davis eventually converted from the rotation to the bullpen and dominated as a closer in '15. Davis got the last three outs in Game 5 of that World Series against the Mets to clinch the title.

Tigers: Detroit lands Miggy in blockbuster

Tigers acquired: Miguel Cabrera, Dontrelle Willis
Marlins acquired: Cameron Maybin, Andrew Miller, Burke Badenhop, Mike Rabelo, Dallas Trahern, Eulogio De La Cruz

Even the bellhops at the Opryland Resort knew Cabrera was going to be traded during the 2007 Winter Meetings; the Marlins made it no secret that their All-Star slugger was on the market. The Tigers’ interest, however, was a secret. Owner Mike Ilitch asked general manager Dave Dombrowski about Cabrera over Thanksgiving weekend and gave his GM the go-ahead to see if he could make a deal. It took a package of young talent that included top prospects Maybin and Miller, but the Tigers outmaneuvered the Angels to swing the deal. The talks were so secretive that Dombrowski sequestered the Tigers staff in their hotel suite while they worked out the details. Manager Jim Leyland was the only one let out so he could go outside and smoke. Cabrera, of course, became a Triple Crown winner, two-time MVP and four-time batting champion in Detroit, and he will go down as the biggest move of the Ilitch era for the Tigers. Maybin and Miller both became productive Major Leaguers, but neither did so in Florida.

Twins: Santana arrives in Rule 5 Draft deal

Twins acquired: Johan Santana, cash
Marlins acquired: Jared Camp

Every now and then, the Rule 5 Draft yields a productive Major League player for a team. It's incredibly rare to see the process produce a franchise-changing talent, but that's exactly what the Twins got when they made a quick swap with the Marlins following the 1999 Rule 5 Draft on the final day of that year's Winter Meetings. The Twins, with the first pick, took right-hander Jared Camp from Cleveland. The Marlins picked second and selected Santana from the Astros. The clubs then made a pre-arranged swap, with the Marlins sending Minnesota some cash with Santana. Camp never made it to the Majors. Santana, on the other hand, broke out with a 2.99 ERA in 2002 and began his string of perennial Cy Young Award contention as one of the most dominant aces in the league. He won his first AL Cy Young Award in '04, was robbed of another in '05 despite almost certainly being the most deserving candidate, and won another in '06, nearly joining Greg Maddux and Randy Johnson as the only pitchers to win three straight. Santana ranked fourth in Twins history in ERA (3.22) and fourth in strikeouts (1,381) over eight seasons -- helping the club to four division titles in that span -- before being traded to the Mets.

White Sox: Podsednik, Vizcaino come aboard

White Sox acquired: Scott Podsednik, Luis Vizcaino, Travis Hinton
Brewers acquired: Carlos Lee

There were rumblings of the White Sox interest in Podsednik on the second day of the 2004 Winter Meetings in Anaheim, but it wasn’t until the Winter Meetings were literally coming to a close that this deal was executed. In fact, general manager Ken Williams spoke of this acquisition at a press conference in front of only a handful of reporters still remaining. Podsednik was one of the many pieces added to reshape a 2004 White Sox team that came close to the postseason but was ultimately knocked down by key injuries to Frank Thomas and Magglio Ordonez. Podsednik picked up 59 stolen bases in 2005 and scored 80 runs at the top of the order with a .351 on-base percentage. It was not uncommon for Podsednik to reach base to start a game, steal second, move to third behind a Tadahito Iguchi grounder to the right side and then be driven home for an early lead. Vizcaino also became a valuable middle reliever for the White Sox, an unsung hero who threw 70 innings in 65 games. Lee hit 60 home runs over two seasons with the Brewers, but the move proved to be key to the White Sox winning the '05 World Series.

AL WEST

Angels: Halos land Downing

Angels acquired: Brian Downing, Dave Frost, Chris Knapp
White Sox acquired: Bobby Bonds, Thad Bosley, Richard Dotson

The Angels made a big trade on the first day of the 1977 Winter Meetings, sending a package highlighted by Bonds to the White Sox for Downing and two others. Bonds was coming off a year in which he hit 37 homers and stole 41 bases, but Downing proved to be one of the best players in Angels history. Downing's 38.0 career bWAR ranks fourth among all Angels position players behind only Mike Trout, Jim Fregosi and Tim Salmon. Downing was an All-Star in 1979 and was inducted into the club's Hall of Fame in 2009.

Astros: Scott deal proves to be steal

Astros acquired: Mike Scott
Mets acquired: Danny Heep

Heep was a struggling reserve player for Houston, while Scott was a fledgling starter who had posted a 5.14 ERA with the Mets in 1982. Scott was added as rotation depth, but he eventually became the ace of the staff. It wasn’t until Astros general manager Al Rosen suggested Scott meet with Tigers pitching coach Roger Craig that the pitcher's career took off. After going 5-11 with a 4.68 ERA for Houston in '84, Scott sought out Craig that winter to learn to throw the split-fingered fastball. The results were immediate. Scott went 18-8 with a 3.29 ERA in 1985 and quickly became a star. He went 18-10 and led the league in ERA (2.22), shutouts (five), innings pitched (275 1/3), and strikeouts (306) in 1986 en route to winning the NL Cy Young Award. He sewed up his Cy Young case when he pitched a no-hitter to clinch the NL West division title against the Giants on Sept. 25, 1986, at the Astrodome. Scott also beat the Mets twice in the NL Championship Series to be named the NLCS MVP, despite the Astros losing the series. Scott won 110 games in nine seasons with the Astros, winning 20 games in '89 and making the All-Star Game for the third time. The Astros retired his No. 33 in '92.

Athletics: Welch joins Oakland in three-team blockbuster

A’s acquired: Bob Welch, Matt Young
Dodgers acquired: Alfredo Griffin, Jay Howell, Jesse Orosco
Mets acquired: Kevin Tapani, Wally Whitehurst, Jack Savage

In an offseason when then-general manager Sandy Alderson bolstered the A’s offense with the additions of Dave Henderson and Dave Parker, the acquisition of Welch from the Dodgers in a major three-team trade involving eight players may have been the key in setting up the club for one of its most impressive three-year runs in franchise history. The A’s reached the World Series in each of Welch’s first three seasons with Oakland, with the right-hander anchoring the rotation each year as he quickly acclimated to the AL by establishing himself as one of the league’s best pitchers. The A’s won the World Series in 1989, and Welch won the AL Cy Young Award in ‘90 after going 27-6 with a 2.95 ERA. Welch finished his career with the A’s, going 96-60 with a 3.94 ERA over seven seasons. After retirement, Welch returned to the organization as a Minor League pitching coach before passing away in a tragic accident in 2014.

Mariners: Canó's historic signing

This one comes with a bit of an asterisk as the official press conference announcing Robinson Canó's signing of a 10-year, $240 million free-agent contract was held in Seattle on the final day of the 2013 Winter Meetings. But all of the club officials and media covering the team flew back from Orlando, Fla., to take part in the biggest announcement in franchise history as general manager Jack Zduriencik finalized a blockbuster contract after outbidding the Yankees for the five-time All-Star second baseman. Canó, along with his agents -- hip hop star Jay-Z and future Mets general manager Brodie Van Wagenen -- were all smiles that day. So was Zduriencik, who called himself “the other J.Z.” Canó wound up playing five years and earning three more All-Star honors for Seattle before being traded to Van Wagenen’s Mets in 2019.

Rangers: 1988 deals change the franchise

Rangers acquired: Rafael Palmeiro, Drew Hall and Jamie Moyer (from Cubs); Julio Franco (from Indians); Nolan Ryan (free agent)
Rangers trade away: Luis Benitez, Pablo Delgado, Paul Kilgus, Curt Wilkerson, Mitch Williams and Steve Wilson (to Cubs); Jerry Browne, Oddibe McDowell and Pete O'Brien (to Indians)

The Rangers had grown stale after going 87-75 in 1986 with an impressive group of young players. Texas followed that up with two straight losing seasons, and general manager Tom Grieve felt the organization needed a major shakeup. By adding Franco and Palmeiro, the Rangers became an offensive powerhouse and maintained that reputation for the better part of 30 years. Adding Ryan was a huge boost to the club's credibility and created the momentum that led to the opening of the Ballpark in Arlington in '94.

NL EAST

Braves: Maddux chooses Atlanta

Hall of Fame executive John Schuerholz went to the 1992 Winter Meetings thinking that reigning NL Cy Young Award winner Greg Maddux would likely end up with the Yankees. As the Meetings progressed in Louisville, Ky., Yanks GM Gene Michael traveled back to New York to show Maddux around town. But New York's $34 million offer wasn’t enough to prevent Maddux from accepting Atlanta’s five-year, $28 million deal. The Braves had won the past two NL pennants, and Maddux felt signing with the Braves gave him his best chance to win a World Series. He would realize this thrill in '95, a year in which he also won his fourth consecutive NL Cy Young Award.

Marlins: 2017 blockbuster in the Cards

Marlins acquired: Sandy Alcantara, Magneuris Sierra, Zac Gallen, Daniel Castano
Cardinals acquired: Marcell Ozuna

The return for Ozuna, at the time coming off back-to-back All-Star selections, makes this trade the biggest Winter Meetings transaction in franchise history. And the good news for the Marlins is that they are still reaping the rewards. Alcantara won the 2022 NL Cy Young Award, and although Gallen has blossomed into an ace following a trade to the D-backs in 2019, the Marlins got back 2022 NL All-Star Jazz Chisholm Jr. As for Ozuna, he spent two seasons with the Cardinals and hit .262 with 52 homers and a .777 OPS before signing with the Braves as a free agent.

Mets: Carter comes to Queens

Mets acquired: Gary Carter
Expos acquired: Hubie Brooks, Mike Fitzgerald, Herm Winningham, Floyd Youmans

Early in the 1984 Winter Meetings in Houston, the Mets traded starting pitcher Walt Terrell to the Tigers for a young slugging infielder named Howard Johnson. That trade would prove to be fruitful for the Mets, but at the time, it was a relatively minor deal. It was not, as manager Davey Johnson told the New York Times, the “big deal'” that could transform the Mets “from a contending team to a dominant team.” That big deal came three days later, when the Mets gave up four players for Carter, an elite catcher who was coming off his sixth consecutive All-Star season. Mets GM Frank Cashen, who had negotiated the trade at the Winter Meetings before flying to Florida to gain Carter’s approval, called it “a banner day for the New York Mets.” He wasn’t wrong. Combined with the team’s acquisition of 1979 NL MVP Keith Hernandez one year earlier, the trade indeed turned New York into one of the NL’s top teams. Less than two years later, it was Carter who leapt into Jesse Orosco’s arms as the Mets celebrated their second World Series title.

Nationals: Wheels put in motion to acquire Turner

Technically, Trea Turner was not acquired by the Nationals until June 14, 2015, but the deal that ultimately landed the star shortstop came during the 2014 Winter Meetings. On Dec. 19, 2014, the Nats made a three-team trade with the Padres and Rays that brought a player to be named later and right-hander Joe Ross to Washington from San Diego. The Nationals sent outfielder Steven Souza Jr. and Minor League left-hander Travis Ott to Tampa Bay in return. That player to be named later ended up being Turner, the Padres' 13th overall pick in the '14 Draft. Turner made his Major League debut two months later, and he helped the Nats win a World Series title in 2019 before being traded to the Dodgers in 2021.

Phillies: Rose joins the Phils

The Phillies needed a jolt after losing in the NLCS three consecutive seasons from 1976-78. They figured Pete Rose could help. Their pursuit of Rose began before the Winter Meetings, with the Phils reminding Rose in Philadelphia that if he signed as a free agent in the AL he could never pass Stan Musial as the NL's all-time hits leader. Rose wanted to make history, but he also wanted to be paid. The Phillies offered a three-year, $2.1 million contract. It was the worst offer Rose received, but he remained interested. Rose’s agent Reuven Katz told the Phillies if they found an extra $100,000 per season, he could convince Rose to sign. Executive vice president Bill Giles got WPHL-TV, which broadcast Phillies games, to kick in an extra $600,000 over the next four years to help pay Rose's salary. Rose signed a four-year, $3.24 million contract, which was announced at the Meetings in Orlando.

NL CENTRAL

Brewers: Crew lands massive haul from Cards

Brewers acquired: Rollie Fingers, Ted Simmons, Pete Vuckovich
Cardinals acquired: Sixto Lezcano, Lary Sorensen, Dave LaPoint, David Green

Milwaukee netted a seven-time All-Star catcher (Simmons) and the next two AL Cy Young Award winners (closer Fingers and starting pitcher Vuckovich) -- not to mention a pair of future Hall of Famers (Simmons and Fingers) -- in a 1980 swap that sent the Brewers on a path to their only AL pennant. A Sports Illustrated headline the following March called it "The Trade That Made Milwaukee Famous." In hindsight, it was a one-sided deal. Fingers won the AL MVP Award and AL Cy Young Award the following season, and he was inducted into the Hall of Fame in '92. Vuckovich tied for the Major League lead with 14 wins in '81 and was the '82 AL Cy Young winner, while Simmons made two All-Star teams with the Brewers and, following a long wait, finally was elected to the Hall of Fame in 2019. Meanwhile, Lezcano and Sorensen never came close to matching the production they'd posted in Milwaukee, pitching prospect LaPoint was a journeyman for 12 Major League seasons, and injuries and off-field troubles contributed to Green, a premium prospect at the time, never making a significant impact.

Cardinals: Herzog shuffles the Cards

General manager Whitey Herzog had been hired halfway into the 1980 season to make the Cardinals a championship-caliber team, and he knew the kind of team he wanted to put together to achieve that goal. His first move at the '80 Winter Meetings was to sign catcher Darrell Porter, the eventual MVP of the '82 World Series. On Dec. 8, Herzog sketched out an 11-player trade with San Diego, sending Terry Kennedy, John Littlefield, Al Olmsted, Mike Phillips, Kim Seaman, Steve Swisher, John Urrea and Bob Geren to the Padres for Fingers, Bob Shirley and Gene Tenace. Four days later, Fingers was traded to the Brewers, along with Simmons and Vuckovich, for the four-player return mentioned above. While that deal didn't pan out quite as well as some of the others, Herzog punctuated the week with a deal to get closer Bruce Sutter, who threw the fastball to Porter that ended the '82 World Series. In all, Herzog made four deals that involved 22 players, turning the Cardinals into a contender -- one that would come to dominate the 1980s.

Cubs: Lester lands on North Side

The Cubs were a young, up-and-coming, prospect-laden club that appeared poised to move out of a rebuild after the 2014 season. That process was accelerated at the '14 Winter Meetings in San Diego, where the North Siders "won the baseball lottery," as former Cubs manager Joe Maddon told reporters at the time. The winning numbers were six years and $155 million, and veteran lefty Jon Lester was the recipient of the biggest free-agent contract for a pitcher in Cubs history. Just like that, there was a true and immediate expectation of not only becoming a winner but contending for a World Series. In Lester's six years in Chicago, the club went to the playoffs five times, won three division crowns, reached the NLCS three times and won the '16 World Series. The lefty was the NL Cy Young runner-up in '16 and the co-MVP of the '16 NLCS.

Pirates: Clemente claimed in Rule 5 Draft

This franchise-changing move didn’t technically take place at the Winter Meetings. According to a United Press story that ran in The Pittsburgh Press on Nov. 22, 1954, the Rule 5 Draft was “generally held in conjunction with the annual Minor League Meetings but … [was] staged separately this year.” Still, the Rule 5 Draft and the Winter Meetings are always associated with one another, so we’re including this transaction here. The Pirates sent Branch Rickey Jr. to those separate “Major League draft meetings” on Nov. 22, weeks before the real Winter Meetings, and paid only $4,000 to select 20-year-old Roberto Clemente from the Brooklyn Dodgers’ Montreal roster. The Dodgers did what they could to hide Clemente and keep him from being drafted, but the young right fielder from Puerto Rico was simply too talented for scouts to not see his talent. Clemente recorded 3,000 hits while winning two World Series during his Hall of Fame career with the Pirates, and he is remembered as the game’s greatest humanitarian.

Reds: Big Red Machine gets key cog

Reds acquired: Joe Morgan, Cesar Geronimo, Ed Armbrister, Denis Menke, Jack Billingham
Astros acquired: Lee May, Tommy Helms, Jimmy Stewart

May hit 39 home runs with 98 RBIs during the 1971 season, but the Reds finished fourth in the NL West after winning the '70 NL pennant. The result was a blockbuster deal at the '71 Winter Meetings that brought Morgan to Cincinnati. He became the catalyst the Big Red Machine needed to reach the next level. Morgan was a back-to-back NL MVP winner in '75 and ’76, the same years Cincinnati won consecutive World Series titles. The Reds’ Modern Era leader with 406 steals, he hit 152 home runs for the club and won five Gold Glove Awards. Morgan was inducted into the Baseball Hall of Fame in 1990, and his No. 8 was retired by the Reds in 1998.

NL WEST

D-backs: The three-team Scherzer blockbuster

D-backs acquired: Edwin Jackson (from Tigers); Ian Kennedy (from Yankees)
D-backs traded away: Max Scherzer, Daniel Schlereth (to Tigers)

It’s important when assessing this 2009 deal to keep in mind that Scherzer had not yet turned into Scherzer yet. He had just completed his first full year in the big leagues, and the D-backs had some concerns about his ability to stay healthy over a long career given the head jerk that was part of his pitching mechanics at that point. Meanwhile, Arizona was looking to add depth to the rotation and jumped at the chance to add two starters for the price of one. While Scherzer would go on to become a three-time (and counting) Cy Young Award winner, the trade was not a complete bust for the D-backs. Kennedy won 22 games in 2011 to help Arizona win the NL West. The No. 2 starter in the rotation that year was right-hander Daniel Hudson, whom the D-backs acquired from the White Sox at the 2010 Trade Deadline in exchange for Jackson.

Dodgers: The one that got away

Although the Rule 5 Draft has become synonymous with the Winter Meetings, the 1954 version was actually held separately. Regardless, that’s when the Dodgers left Roberto Clemente unprotected and former Dodgers club president Branch Rickey Jr. snagged him for the Pirates in the Rule 5 Draft. Although the Dodgers won four World Series during Clemente’s Pittsburgh career, one can only wonder how much more dominant they could have been with the future Hall of Famer still in the fold.

Giants: Bonds lands by the Bay

The Giants arrived at the 1992 Winter Meetings in Louisville looking to make a splash after a new ownership group, led by Peter Magowan, managed to save the team from relocating to Florida. Magowan immediately ushered in a new era for the franchise by signing superstar slugger Barry Bonds to a six-year, $43.75 million deal, then the richest contract in baseball.

“It’s a lot of money, but there’s only one Barry Bonds,” Magowan said during the introductory press conference.

The move represented a homecoming for Bonds, whose father, Bobby, and godfather, Willie Mays, both played for the Giants. Bonds went on to carve out his own legacy in San Francisco, where he hit 586 homers over 15 seasons en route to becoming baseball’s all-time home run leader.

Padres: Brown deal pays dividends

Padres acquired: Kevin Brown
Marlins acquired: Derrek Lee, Steve Hoff, Rafael Medina

At the 1997 Winter Meetings, the Marlins were looking to sell coming off their World Series title. The Padres were on the cusp of making their own run to the World Series and looking to buy. The two sides came to an agreement on the final day of the '97 Meetings in New Orleans. Brown had only one year remaining on his contract, but he made the most of it. There's an argument to be made that Brown's 1998 season is the most impactful single season in franchise history. He posted a 2.38 ERA with seven complete games and three shutouts, then dominated in the postseason. Brown was the biggest catalyst for the Padres winning their second NL pennant in ‘98.

Rockies: Hampton's landmark contract

Star righty Darryl Kile went 21-30 with a 5.84 ERA for the Rockies from 1998-99 before being traded to the Cardinals -- where he went 20-9 with a 3.91 ERA in 2000. So the Rockies desperately wanted to put a lid on the notion that no one could pitch at the Coors Field altitude. Also, after years of filled stands during the franchise’s early years, ownership saw an inevitable attendance decline coming. So if creating a buzz as the 2000 Winter Meetings in Dallas was the goal, signing Mike Hampton to the then-largest contract ever bestowed upon a pitcher (eight years and $121 million) certainly did the trick. Earlier in the winter, Colorado had signed lefty Denny Neagle for five years and $51.5 million. Neither contract produced the desired results, with Hampton going 21-28 with a 5.75 ERA in two seasons with the Rockies before being traded to the Marlins following the 2002 season (and then to the Braves just two days later). To this day, the team has avoided high-profile free-agent pitchers -- and has seen more success with pitchers they either developed through the farm system or acquired early in their careers.