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Three Cubs winter meetings questions: Is Tyson Ross a possibility?

WASHINGTON, D.C. -- The Chicago Cubs head to the winter meetings as defending champs for the first time, and they are searching for depth in their pitching staff to ensure a good opportunity to repeat. Here are three questions to ponder as agents and team executives descend on the nation's capital.

Will the Cubs pull the trigger on a deal for another young starter, and will they trade from their major league core to do so?

Remember, after several attempts, the Cubs finally got a young, controllable pitcher in Mike Montgomery when they traded prospect Dan Vogelbach to the Seattle Mariners last season. But they undoubtedly want more, as Montgomery might be best used as a sixth man/hybrid who starts the season in the bullpen. Plus, the Cubs have soon-to-be free agents in Jake Arrieta and John Lackey, so planning for the future has always been a priority for the Cubs' front office.

You can bet the Cubs and Tampa Bay Rays are talking about a number of pitchers, from Chris Archer to Jake Odorizzi to perhaps even closer Alex Colome.

The Cubs have shown a propensity to bring in people they know, including personnel who worked with Theo Epstein in Boston and those who worked with Joe Maddon in Tampa Bay. Archer would be the prize, but you better believe the Rays would ask for players such as Javier Baez or top prospect Eloy Jimenez in return. A smaller deal is more likely, as Jorge Soler could be part of a trade for a less-heralded player. You can be assured that the Cubs aren't moving any of their top core players, so Baez could be the carrot -- though there's no reason to believe they're looking to deal him. Anything involving Baez would have to be something the Cubs couldn't refuse.

Is Tyson Ross a possibility?

On Jan. 21, 2004, the Cubs signed Ryan Dempster to a free-agent deal months after he underwent Tommy John surgery. He didn't pitch until August of that season but went on to play for the Cubs until 2012, when he was traded for Kyle Hendricks at the trade deadline. That signing paid off in a big way.

The Cubs can use the same strategy with Ross, whom the San Diego Padres let go after not tendering him a contract for 2017. The Cubs sought him in a trade but can now obtain him for nothing -- though he's coming off surgery for Thoracic Outlet Syndrome, the main reason he was let go. Who knows if Ross can return to the form that produced ERAs of 3.17, 2.81 and 3.26 in three seasons prior to his injury, but the Cubs are the perfect team to allow him to try at his own pace.

In other words, their hopes for 2017 don't hinge on Ross, but a potential multi-year contract with incentives makes more sense than the Cubs rehabbing him and letting him back on the market next winter. Dempster had a team option for Year 2; a similar deal for Ross would make sense.

Is free agency an option after last winter’s spending spree?

The Cubs said they did two offseasons worth of shopping last December, but that doesn't mean they don't have the means to sign a player at a decent rate. They already inked Jon Jay for $8 million and Brian Duensing for $2 million, but that's pennies compared to what the top free agents will receive.

Dexter Fowler is off the books (for now), as is Edwin Jackson (remember him?), and the Cubs get savings on Travis Wood right now as well. With only four arbitration-eligible players getting modest raises, the Cubs should have the ability to sign one of the closers on the market, if they can get one at the right price. Other than that, there isn't a good reason to spend a large amount on anyone else. It's Aroldis Chapman or Kenley Jansen, or the Cubs will fortify with smaller deals.