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Boldest January signings of this century

Mega-deals, extensions frequently occur during first month of year
MLB.com @mattkellyMLB

The holiday season is finished, and as the country gets back to business, there is still plenty of work for MLB teams to do on the free-agent market.

Many marquee position-player free agents remain available, as do big-time starters like Jake Arrieta and Yu Darvish. After one of the slowest Decembers in recent memory, January is shaping up to be a frenetic time on the Hot Stove.

The holiday season is finished, and as the country gets back to business, there is still plenty of work for MLB teams to do on the free-agent market.

Many marquee position-player free agents remain available, as do big-time starters like Jake Arrieta and Yu Darvish. After one of the slowest Decembers in recent memory, January is shaping up to be a frenetic time on the Hot Stove.

We've yet to see a true mega-deal this winter, but recent history says this month can yield plenty. The following is a retrospective of the biggest January contracts signed this century.

2016
Jan. 6: Royals sign Alex Gordon for four years, $72 million
Jan. 20: Tigers sign Justin Upton for six years, $132.75 million
Jan. 21: Orioles sign Chris Davis for seven years, $161 million
Jan. 26: Mets sign Yoenis Cespedes for three years, $75 million
Kansas City selected Gordon with the No. 2 overall pick in the 2005 MLB Draft, and it rewarded the foundational member of its back-to-back American League pennant-winning clubs two years ago at this time. Gordon captured his fifth AL Gold Glove Award in left field this past season, but he has struggled to a .214 average and league-adjusted 73 OPS+ since re-signing with the Royals.

Two weeks after the Gordon deal, one of the Royals' AL Central rivals made a huge splash by inking Upton. The Tigers had finished near the bottom of the AL in offense in '15, and envisioned Upton bolstering the middle of their lineup beside Miguel Cabrera and J.D. Martinez. Upton performed ably, if not tremendously, in '16, but Detroit's tough start to '17 -- along with Upton's looming opt-out clause -- brought about his trade to the Angels at the Aug. 31 waiver deadline.

Baltimore's top priority was re-signing Davis, and it gave the fan favorite the most lucrative contract in team history. Davis responded with a 38-homer campaign in 2016, but declined to 26 dingers while batting .215 this past season at age 31. His deal includes $42 million in deferred money that will be paid to him over a 15-year period after his contract ends in 2023.

Both the Mets and their fans had appeared to have given up hope for Cespedes' return after his heroic close to 2015, but an offer from the rival Nationals spurred New York's front office into action. The Mets convinced Cespedes to ink a three-year deal that included an opt-out clause after the first season. The star outfielder opted out in the fall of '16, before inking a four-year, $110 million deal to stay in Queens.

Video: ARI@NYM: Cespedes belts a solo homer to left-center

2015
Jan. 18: Nationals sign Max Scherzer for seven years, $210 million
The Nationals' pitching staff led the Majors with a 3.03 ERA in 2014, but general manager Mike Rizzo still acquired the top free-agent starter in Scherzer. The righty is on Washington's books through 2028 with deferred money, but it's hard to imagine a mega-deal starting much better. Scherzer finished fifth in the National League Cy Young Award vote with a 2.79 ERA in '15, and then went on to capture the award in each of the past two seasons. Scherzer's overall numbers with the Nationals so far: A 50-25 record with a 2.76 ERA and 11.3 strikeouts per nine innings.

Video: Scherzer talks about winning his third Cy Young Award

2014
Jan. 15: Dodgers sign Clayton Kershaw to seven-year, $215 million extension
Jan. 22: Yankees sign Masahiro Tanaka for seven years, $155 million
Jan. 26: Brewers sign Matt Garza for four years, $50 million
It's truly hard to imagine Kershaw pitching in any color besides Dodger Blue, and Los Angeles locked down Kershaw -- at least temporarily -- with a deal that paid him a $30.714 million average annual value and made him the highest-paid pitcher in history. Kershaw's leverage couldn't have been any better; he was coming off his second NL Cy Young in a three-year span, as well as his third consecutive ERA title. But intrigue may be coming soon for the Dodgers and Kershaw, whose opt-out clause could put him back on the market next offseason.

The Yankees locked down their ace after sending an eight-person contingent to California to meet with Tanaka and his agent, Casey Close. Not only did Tanaka's contract include $155 million, but the righty also received a full no-trade clause and an opt-out, which he declined this past November. Tanaka has been excellent while pitching in pinstripes, compiling a 52-28 record and 118 league-adjusted ERA+ over his four seasons in the Bronx.

Video: Tanaka declines to opt out, will stay with Yanks

In Milwaukee, the Brewers' rotation ranked near the bottom of the NL in 2013, so a steady innings-eater like Garza seemed like a fit. Garza's deal was the richest in Brewers' history, but unfortunately, the right-hander has been below average while posting an 87 ERA+ and battling injuries over his four years with the Crew.

2012
Jan. 18: Rangers sign Yu Darvish for six years, $56 million
Jan. 24: Giants re-sign Tim Lincecum for two years, $40.5 million
Jan. 26: Tigers sign Prince Fielder for nine years, $214 million
Texas paid a hefty price for Darvish, first winning the right to negotiate by submitting a $51.7 million posting bid to the Nippon-Ham Fighters and then giving Darvish $56 million in guaranteed money. But Darvish was an AL All-Star four times for the Rangers -- pitching around the Tommy John surgery that sidelined him for the entire 2015 season -- and posted an average of 11 strikeouts per nine innings, which has him on track to be one of the best in history in that regard.

The Giants scrambled twice in a span of three years to avoid arbitration with Lincecum, who first asked for a record $13 million in 2010 and then upped the ante to $21.5 million -- another record -- in '12. San Francisco held on to the two-time NL Cy Young winner, but unfortunately, Lincecum's career headed south immediately after the ink was dry. Lincecum posted a 137 ERA+ over five seasons before signing the deal, but has been well below average while struggling with injuries (and later moving on to the Angels) since then.

Darvish and Lincecum were headline deals, but nothing approached the agreement reached by Fielder and the Tigers. The Brewers were out early when agent Scott Boras informed them that Fielder's asking price would start at approximately $200 million, and the Tigers swooped in after Victor Martinez tore his ACL during offseason training. Pairing Fielder with Cabrera made the Tigers a clear favorite after their run to the 2011 AL Championship Series, but he played just two seasons in the Motor City -- albeit strong, All-Star campaigns -- before he was dealt again to the Rangers, along with $30 million, in exchange for second baseman Ian Kinsler. An extremely durable player for his entire career, Fielder underwent a neck surgery that ended his '14 season and allowed himi to play just one more full year in Arlington before he retired in '16.

Video: ALCS Gm5: Fielder singles up the middle in the first

2011
Jan. 5: Rangers sign Adrian Beltre for five years, $80 million
Texas was coming off its first World Series appearance and already had a solid third baseman in Michael Young. But general manager Jon Daniels prevailed in a bidding war that included the Red Sox, Angels and Nationals, signing Beltre and moving Young to designated hitter. It's interesting to think about the trajectories of those clubs had they signed Beltre, whose late-career resurgence ranks among the best in recent memory. Beltre has been the game's third-most valuable player according to Baseball-Reference's Wins Above Replacement (WAR) metric since he first put on a Rangers uniform in 2011 at age 32.

2010
Jan. 5: Cardinals sign Matt Holliday for seven years, $120 million
Jan. 21: Mariners sign Felix Hernandez to five-year, $78 million extension
The A's traded Holliday to St. Louis in July 2009, and his red-hot performance down the stretch (.353 average with 13 home runs and 55 RBIs in 63 games) convinced the Redbirds to make him the highest-paid player in team history. Holliday was expected to be the perfect lineup complement to Albert Pujols, until Pujols left for Anaheim the following winter. Still, Holliday filled in ably as the Cardinals' power threat, posting a 140 OPS+ from 2010-15.

Meanwhile, there had long been speculation that Seattle would not be able to afford, or convince, Hernandez to stay in the Pacific Northwest. But the Mariners have met the call with two massive extensions for Hernandez in recent years. The first came in 2010 following the team's acquisitions of Cliff Lee and Chone Figgins, as well as an extension for Hernandez's close friend, Franklin Gutierrez. Those moves persuaded Hernandez to forgo free agency, and he immediately followed up with an AL Cy Young Award season, in which he led the Majors with a 2.27 ERA. Seattle extended Hernandez again with a seven-year, $175 million deal in Feburary 2013.

Video: OAK@SEA: Felix fans six over six solid frames vs. A's

2009
Jan. 6: Yankees sign Mark Teixeira for eight years, $180 million
Jan. 13: Braves sign Derek Lowe for four years, $60 million
An 89-73 record in 2008 spelled an October without postseason baseball in the Bronx for the first time in 14 years, and the Yankees reacted swiftly. The Yanks signed A.J. Burnett and CC Sabathia for a combined $243.5 million, before also inking Teixeira to man first base. Stepping in for the departed Jason Giambi, Teixeira paired 39 home runs with Gold Glove-caliber defense to finish second to Joe Mauer in the AL MVP race. More importantly, the Yankees captured their first World Series championship since 2000.

Atlanta icon John Smoltz switched to a Red Sox cap in the winter of 2008, but the Braves responded by inking the dependable Lowe. A World Series hero for Boston himself, Lowe averaged 14 wins and 213 innings per season over a four-year tenure with the Dodgers and figured to bolster a Braves club that slipped to 72-90 in '08. Lowe did just that in '09, going 15-10 while throwing 194 2/3 innings, and was even better for the Braves' playoff-bound squad in '10. Lowe's extensive workload finally caught up to him the following year at age 38, and he spent the final season of this contract with the Indians and Yankees in 2012.

2005
Jan. 13: Mets sign Carlos Beltran for seven years, $119 million
Jan. 21: Astros sign Roger Clemens for one year, $18 million
Jan. 26: Marlins sign Carlos Delgado for four years, $52 million
Beltran and Delgado famously occupied the same lineup in Queens, of course, but their paths first diverged in January 2005. A no-trade clause and a recruiting trip to Beltran's native Puerto Rico convinced the All-Star center fielder to leave the Astros after his historic '04 postseason and join the Mets. New York reportedly made the exact same offer as the Marlins did to Delgado, but the Fish prevailed … until they traded the slugging first baseman to their division rival the following winter.

Meanwhile, Clemens convinced the Astros to make him the highest-paid pitcher in history after he'd captured his record seventh Cy Young Award. The only question remaining was if he could convince himself to return at age 42. The answer was yes.

"Here we go again," Clemens said at the official news conference for his record deal. "I've got to go get ready to play again." The Rocket went on to post an incredible 1.87 ERA that year -- giving him his seventh career ERA title -- while helping Houston reach its first World Series in franchise history.

2002
Jan. 9: Astros sign Billy Wagner for three years, $27 million
Jan. 14: Giants sign Barry Bonds to five-year, $90 million extension
Wagner overcame a small frame and a broken right arm to become one of the best left-handed relievers in baseball, and the Astros rewarded him with a deal that put him just behind Mariano Rivera for the highest annual average value for any reliever at the time. He put together two more stellar seasons in Houston before the Astros traded him to Philadelphia to cut costs in November 2003.

Bonds' signing with the Giants in 1992 changed the courses for both San Francisco and Pittsburgh, and this extension allowed both sides to avoid arbitration and keep the legend in a Giants uniform for the rest of his career. After the ink dried, Bonds led San Francisco to within a game of the '02 World Series title, claimed three more NL MVPs and broke Hank Aaron's career home-run record. It's safe to say the extension was a no-brainer.

Video: Bonds holds all-time record for home runs with 762

Matt Kelly is a reporter for MLB.com based in New York. Follow him on Twitter at @mattkellyMLB.