What is the likelihood of a Kris Bryant trade to the Phillies?
-- @mcnultyk9 via Twitter

I touched on this in last week’s Inbox, but I think it’s worth revisiting: It’s difficult to see how the Phillies match up with the Cubs (or other teams potentially trading a superstar this winter) unless they decide to gut their farm system. The organization has three players ranked among MLB Pipeline’s Top 100 Prospects: infielder Alec Bohm (No. 34), right-hander Spencer Howard (No. 88) and shortstop Bryson Stott (No. 89). Figure the Cubs require at least two of them to be included in any deal for Bryant. If the Phillies agree to that, their system takes a crippling hit, because it is so top-heavy. Philadelphia's farm system ranks somewhere in the No. 16-20 range largely because of Bohm, Howard and Stott. If other recent top Draft picks and international free agents had developed as hoped (e.g. Mickey Moniak, Cornelius Randolph, Jhailyn Ortiz, Kevin Gowdy, Cole Stobbe, etc.) or not stumbled in 2019 (e.g. Adonis Medina) the Phillies might be more willing to include one of their top three -- or one of those other players could be included instead. Alas, it is not the case.

The Phillies have financial flexibility, so they can take on a bad contract to help ease their prospects burden, but I’m not sure the Cubs deal Bryant without a significant return. It would be a tough sell to their fans. Never say never, but don’t bet a mortgage payment on it, either.

Will the Phillies sign Didi Gregorius? If so, they can shift Scott Kingery or Jean Segura to third and get rid of Maikel Franco. Will they resign Corey Dickerson?
-- @Lucky4583 via Twitter

MLB.com’s Mark Feinsand and Jon Paul Morosi both reported the Phillies have interest in Gregorius. It’s an intriguing possibility, because Gregorius is entering the market following a down year, but he has plenty of upside. Gregorius would bump Jean Segura to second base or third base. In that scenario, Scott Kingery plays the remaining infield position. Or the Phillies move Segura to third, keep César Hernández at second and play Kingery in center field. Regardless, I don’t see Franco returning in 2020. I don’t see Dickerson returning, either. The Phillies already have Bryce Harper, Andrew McCutchen and Jay Bruce to play the corners. Adam Haseley, Roman Quinn, Nick Williams and Odúbel Herrera are on the 40-man roster, too. (I don’t expect Herrera to be back in 2020.)

What do you think the Phillies chances are of landing one of the big free agents such as Gerrit Cole or Anthony Rendon are?
-- @bsp1952 via Twitter

The Phillies are not in the same position as last winter, when there appeared to be few suitors for Harper and Manny Machado. Think about it: Harper’s decision came down to only three teams: Philadelphia, Los Angeles and San Francisco – and the Dodgers only made a short-term offer. I suspect there will be more competition this time, or at least more aggressive suitors. It means the Phillies might not be able to count on free agents coming to them like last winter.

Which hitter is most likely to see a positive impact from a new hitting coach? Which pitcher is most likely to see a positive impact from a new pitching coach?
-- @DroppedStrike3 via Twitter

Pitching coach Bryan Price should be able to help everybody on a pitching staff that took a collective step backward last season. Even though the Phillies might not be counting on Nick Pivetta and Vince Velasquez to round out the rotation in 2020, they still have a lot of talent, and it will be interesting to see if Price can tap into it. Hitting coach Joe Dillon seems to have a healthy mix of modern and traditional approaches to hitting. Imagine if he gets Rhys Hoskins back on track after struggling in the second half. Mix in a third baseman like Mike Moustakas, and the Phillies’ lineup becomes much more potent.

I’ve seen a lot of people calling for Kingery to have an everyday spot. I was under the impression they signed him specifically to be the Swiss Army knife-type of player. Do the Phillies care if he never plays second?
-- @trevorpjames via Twitter

The Phillies’ front office believes pushing somebody to play only one position is antiquated, even if Kingery’s best position is second base. They believe he is an above average defender wherever he plays, so they feel no need to force the issue to play him there. I can see Kingery playing regularly at one of three positions next season: second, third or center.