though would you want to know first or last? Seems first might be the most compassionate.
Well if you're legit asking this and not just being playful the way I look at it is this. It's clear he favors the west coast. So the fact that a FA of his caliber is even considering the cubs is interesting. Admittedly I'm apparently a fair bit different than most sports fans but to me wins and losses aren't zero sum games. The term participation trophy gets thrown around a lot these days by people my age or old but I truly believe if you put your best foot forward and come up second there's no shame in that.
As that pertains to Ohtani, one of 3 things happens. A) he goes to one of the 5 west coast teams in which case i mean what can you really do if you're the cubs? B) he goes to the rangers because presumably they offer him $3.5 mil that no one else can offer. If that happens.... again, what can you do? Obviously if the cubs had known he'd be available during this period they may have adjusted their IFA spending in 2015 but you couldn't have know. C) The cubs out sell in their presentation options A and B.
If I had to hazard a guess, I think it's going to be fairly easy to argue against the rangers. They were a middling team that finished 23! games back of the astros last year. They had 6 hitters over 2 wins(Andrus, Beltre, Gallo, Chirinos, DeShields and CarGo) and of the remaining guys only Mazara is really intriguing. Maybe you argue Profar is but think that's a stretch at this point. They had Darvish as a pitcher over 2 wins but emphasis on had. Beltre is 39! and a FA after 2018. Andrus is there for the long haul(signed thru 2022). Chirinos is 34 and signed for 2 more years assuming they pick up his option. CarGo is a FA this year. They also have Hamels for another two years but at 34 doubt you're expecting too much there. So realistically speaking their core is Andrus, Gallo, Mazara and DeShields. Leody Taveras and Willie Calhoun are decent prospect but neither is likely better than say Happ is.
If you're the cubs I think selling against that is a pretty simple argument. Not one of those players is Kris Bryant. Not one of those players is Anthony Rizzo. Hell I'd probably take Contreras over any one of those players given how hard it is to find a good catcher these days. So if he goes to Texas think the only reason is money. But clearly money doesn't appear to be a high priority for him given the yankees didn't even make the cut and given the majority of the 7 remaining teams can only offer him $300k.
So from my vantage point it comes down to how do you outsell the west coast. My only answer to that is you don't. You sell what you offer that none of those 5 west coast teams can. I've seen some talk of them potentially offering to run a 6 man rotation like they do in japan. Most teams aren't going to do that but frankly the cubs basically were doing that last year anyways. You also can sell him on Maddon doing weird Maddon things like playing a reliever in LF or batting Rizzo lead off. You sell him on the culture Maddon has brought to the cubs(post game victory celebrations and fun ideology).
Ultimately if that doesn't work then it doesn't work but I'd be rather surprised if he ends up in Texas. In my eyes it's either the best west coast team that fits him or the cubs.