Alright, I'm going to bump this thread in hopes of a CBA being agreed to in the next week. From my perspective, I think the Sox will have five priorities heading into part two of the offseason:
Add a left-handed power bat, preferably one that can play a solid RF
Acquire a #3 type SP via trade, likely on a one-year deal to limit cost
Sign or trade for a cheap 2B, possibly one who can platoon with Leury
Trade Kimbrel for salary relief and major league depth / role players
Sign a decent reliever to fill-in behind Hendriks, Bummer, & Graveman
With those focus areas identified, here's how I could see Hahn addressing them. As I've stated numerous times, Michael Conforto is a perfect fit for this roster as he's elite against RHP (our biggest weakness on the positional side) and is more or less average in RF (a massive upgrade from Vaugh / Sheets though). He should without question be the number one priority when a CBA is agreed to and I truly believe he ends up on the South Side. To round out the lineup, I'd go ahead and sign Brad Miller to a cheap deal to be the strong side of a 2B platoon with Leury. Miller posted a 123 wRC+ against righties last year and has been solid at 2B from an advanced metrics perspective. Combine him and Leury and I think you can easily get two wins out of the position for dirt cheap.
From there, the focus turns to the rotation. The challenge addressing this need is twofold. First, free agency is running out of quality options. The only two guys I'd argue are #3 starters or better are Kershaw & Rodon. Both have serious health concerns and we already passed on the opportunity to lock Carlos in via a QO. As such, that pretty much forces us to go the trade route unless we're willing to bank on a guy whose stuff continues to regress each year (Keuchel) and a guy who will be on an innings limit (Kopech) to cover 40% of our rotational needs. The problem here is we have the worst farm system in baseball. I'd love to go out and acquire Sonny Gray, but we don't have the pieces to get such a deal done unless we absorb a bad contract (say Moustakas) or are willing to give up Vaughn. That basically leaves guys who are on one year deals with rebuilding clubs. The A's have a couple of these guys and I really think Bassitt could be had for a package built around Burger & Dalquist.
Finally, the Craig Kimbrel situation has to be addressed. I supported the trade at the time, but it was an unmitigated disaster in hindsight. However, the reality is we need to move on (we simply can't afford both him & Hendriks) and recoup whatever value we can, even though it will certainly be less than what we gave up. I still see the Phillies as the likely landing spot here. In terms of return, I'd expect us to get a couple of major league role players. The main piece I could see happening is Rafael Marchan, a 23 year old, defensive oriented switch-hitting catcher who can immediately challenge Collins for the backup spot behind Grandal. A second piece that seems possible is Jose Alvarado, a 26 year old, left-handed reliever with big stuff but who has struggled with control the past couple years. He's definitely a project but one worth seeing if a change of scenery with Katz can unlock his 2018 form (2.27 FIP | 2.1 fWAR). I know many here would be disappointed with that return while others will think it's unrealistic, but it feels about right to me given the Phillies' desperate need for a closer. Regardless, moving Kimbrel requires us to add a reliever IMO and I think bringing back Tepera makes the most sense. His age and lack of track record should keep the price reasonable and he showed some serious stones in game 3 against the Astros.
Make these moves and I think we've got as strong of a roster as any team in baseball.