The flaw in your argument, IMO, is that the Betts and Machado trades occurred before COVID-19. The world has since changed and MLB economics have been completely upended, particularly for small market teams.
I understand your point for making trades now .... but, the question is by July, the worst of this COVID should be over and spending a few million by a top market team for a playoff birth should have started to return to the Machado rental return. ... I didn't even bring up Betts; I knew we wouldn't have gotten that at this point of time.
I was starting to think that the Indians might have kept Lindor and Carrasco due to the light return market as we saw with Darvish and Snell. Yet, Dolans are really financially tied as from a financial perspective ... what would the $20 million for Lindor and $12 million for Cookie gotten you down the road?
a) An increase in fan base this summer when they could start drawing crowds ... now come July, we will be talking a Ramirez trade in offseason versus a playoff race
b) An increase in your TV market share -- 2 years out from a deal renewal
Now, I said this elsewhere, from a business sense, if they could have kept there market share up during negotiations, Lindor's $20 million spread over 10 years is really $2 million ($5 million if you could have paid him $30 for 2022 as a one year deal). Now, if they could have locked in new TV deal after 2021, that small change (increase in market share) should have gotten you another $2-$5 million per year at least on a $60+ million per year deal than see your market share crash by 20-30% due to lack of excitement/playoff run and try to maximize your deal on that share drop. Now, this wasn't that realistic as the deal expires after 2022 so Lindor was going to be gone anyway. Yet, to trade your 2nd/3rd best pitcher as well and drop out of any playoff run for sure, it makes the viewer anger and careless even greater. Look at other sports viewership drop during COVID mess ... Indians didn't do so bad comparatively as we were in a playoff run last year. Watch this potential TV deal to start to crater as well. Don't expect the deals signed a few years ago by Tampa and others to provide the extra money we need to sign Bieber and next round of talent long-term. This downward spiral could be the beginning of the end to the Dolans and possibly Cleveland. If you couldn't even afford $60 million .... that means the financial situation is not just tight but dire.