The Cubs have had a knack for striking it big at baseball's winter meetings, as they did in December 2014 when they signed free-agent left-hander Jon Lester to a six-year, $155 million contract.
And they can strike quickly, as they did a year later when they signed Ben Zobrist to a four-year, $60 million contract and traded infielder Starlin Castro in a span of less than two hours.
But with so many issues to address, the Cubs could work at a more deliberate pace and let the market dictate some of their moves.
Nevertheless, the need for pitching is so urgent that you can expect them to be linked to several starters and relievers from the time the winter meetings begin Sunday in Orlando, Fla., until after the Rule 5 draft Thursday.
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The Cubs on Thursday signed free-agent right-hander Tyler Chatwood to a three-year, $38 million deal, filling a back-of-the-rotation spot behind Lester, Kyle Hendricks and Jose Quintana. Chatwood, 27, is 40-46 with a 4.31 ERA in 130 major league appearances – including 113 starts – with the Angels (2011) and Rockies.
But with the likely departures of free agents Jake Arrieta and John Lackey – 40 percent of their rotation over the last two seasons – the Cubs still need a starter.
They wouldn't mind paying a $20 million posting fee to the Nippon Ham Fighters for Shohei Ohtani. The 23-year-old Japanese star – a right-handed power pitcher and left-handed-hitting outfielder – selected the Cubs as one of his seven finalists, though they are the only one located east of the Mississippi River.
Right-hander Alex Cobb, 30, who pitched for manager Joe Maddon and pitching coach Jim Hickey with the Rays, remains on the Cubs' short list but is entertaining interest from several teams.
The Cubs would like to re-sign closer Wade Davis, who had 32 saves and a 2.30 ERA last season. But Davis, 32, likely will command a multiyear contract at about $15 million annually. Maddon has handled bullpens with more than one closer, and the Cubs need multiple relievers to replace Hector Rondon and probably Davis.
The Cubs also are putting a premium on control pitchers because their relievers last season walked 264 batters – the fourth highest total in the National League. That's why right-hander Brandon Morrow, who has closing experience and walked only 1.9 batters per nine innings with the Dodgers in 2017, is an attractive option. Other free-agent relievers with exceptional control are righty Brandon Kintzler, who has a lifetime 2.2 walks per nine innings, and lefty Jake McGee, who pitched for Maddon and Hickey with the Rays.
Even if the Cubs don't make another big splash at the meetings, they could lay the groundwork for future deals, as was the case in January 2015 when they acquired leadoff hitter Dexter Fowler from the Astros.
The Cubs and Rays have scouted each other's players closely, from right-handed starters Chris Archer and Jake Odorizzi of the Rays to shortstop Addison Russell and infielder Javier Baez.
But youngsters Kyle Schwarber, 24, and Ian Happ, 23, could be targets for interested teams, with Schwarber potentially helping an American League team in need of a left-handed power hitter and the switch-hitting Happ's versatility as a second baseman and outfielder making him an attractive option.
Cubs management understood the 2017-18 offseason would be one of their most challenging – and the process could seem as lengthy as the mission they started in 2012.