A couple things to think about ...
1) "We have a chance this year" ... and so do the Rockies. It's kind of like saying Mavs or Cavs have a chance to win against Lakers. The average sports book is 1:38 this year for us to win WS, 1:30 last year (average of just being in MLB) and 1:10 in 2019.
2019 was year to go all in and we tried to split the Trevor trade in MLB guys (Puig and Reyes) and prospects (Allen, Moss, Nova) -- similar to Clev trade MLB guys (Naylor, Quant, Hedges) and prospects (Cantillo, Arias and Miller). This is spreading out your bets between now and future. For a team with limited resources, in my mind, they got to either go all in or pull back resources for later. Indians try to split the difference to stay competitive but not really have a chance to compete in October.
2) "Rather be winning than losing" -- "just making playoffs is good enough". Imagine asking the Cubs (if they lost Game 7 to us instead) if it would have been good enough to get to game 7 and lose while going onto a 110 year WS drought this year. Ask a Bills fan about 4 SB appearances in a row and "wide right" if that was good enough. We are still living in Cavs glory. Yet, think about if Cavs lost that last game to GS, how would be feel about being the proverbial "Bridesmaid"/ 2nd Best in Cleveland. When will this 70+ year on-going drought start dragging down Indians fans (if Browns don't win -- it will be soon).
3) "But we were 1 game from having 2nd best record in AL last year" -- partially due to Central sucking. The strength of the central is the reason why Cards and WSox only won 1 WC game and Twins and Indians won 0 WC games last year (2 out of 10 games - odds should have been that 2 teams moved forward if evenly competitive). Teams that won were all from East and West because they are better.
4) "We just need one more good hitter to protect Jose" -- I like our top 3 in Cesar, Jose and Eddie. Yet, after than it becomes slightly above average AAAA roster at best -- in Reyes (a 1-2 WAR DH -- not Cruz or Stanton type), Naylor (hope he gets his Top 100 prospect luster back), Perez (defense only), Mercado (don't get me too down or I will be sent down again), Bradley/ Bauers/ Johnson, Rosario/ Gimenez at SS. You need 3 of them to break out to even come close to a Twins/Sox/Yankees or Dodgers line-up. And, unfortunately, most teams are also have 2-3 pitchers at their FOR that can compete with ours (if not be better like Dodgers/Padres). We can't even say that our staff is top-5 unlike 2019/20.
5) "We have 2 of the best pitchers/hitters in the league." Unfortunately, this isn't the NBA where LeBron/Kyrie or LeBron/Davis can carry you deep in playoffs not matter the supporting cast.
You can point to Hershiser in 1988 (NLCS - Game 1, Game 3, save in Game 4 and Game 7 ... WS Game 2 & 5) -- carried the weak offense of Dodgers. Yet, when MLB added Central and 3rd series plus WC (vs old 2 series to win it all), the odds of the underdog (David beating 3 Goliaths) went down and days where a pitcher can go on all 3 days rest is long gone. Longer and more series - the more odds start to favor the goliaths vs upsets. Easier to get lucky in 2-4 games to turn 2 playoff series around than 3-6 games needed over 3 playoff series (like flipping a coin and expecting a heads to always appear - more you play the less the unusual happens).
6) "You are going to waste your pitching" --But, If you don't have hitting, you are going to waste your pitching anyways. For me, just appearing in a 1 game WC isn't good enough. For some it is and thus you would want to hold tight and hope that Bieber can pitch a Orel-type 54 innings of shutout ball (3-series for 6-games/9 innings) and hope for Ramirez HR in each game. If it is good enough for you, then we just need to agree to disagree.
Indians are basically already wasting their pitching due to the financial cuts we made (and the 1/2 in - MLB players and 1/2 out - prospects trades). If you think that we can be a better team due to
- Trading Lindor and Cookie for A Rosario and Gimenez (and getting 2 prospects back) -- and even with Rosario and Gimenez, we are only going to see 1 play at SS at a time. A Rosario isn't just going to play SS in April/May then say ... I can play CF with no practice time in ST. We lost immediate value (help) here.
- Switching out Santana (yes he and Lindor had an off year) with E Rosario (isn't an major improvement). There is a reason Santana commanded 2 for $17.5 million vs Rosario 1 for $8 million. Best you can call this is a draw or slight upgrade as we needed an OF (as Naylor, Bradley and Bauers are better at 1st).
- You can say that Clase will be (maybe) better than Hand - but other teams have rookies or 2nd year players coming up too. I just don't see a major upgrade to this team over last year (unlike Sox/Toronto/Padres and others have had). With our better young hitters still 1 to 2 years away, we didn't fill the holes we had -- bottom part of line up (just traded one for another)
7) "Trading Jose will give us too many prospects w Rule 5" -- Issue isn't having too many prospects, the issue is when you trade a damage Clevinger, nut-case Bauer, older Cookie or 1-year of Lindor, this approach doesn't give you enough 50+ FV top-line prospects (the next Lindor, Tatis, ...) but gives you guys with some holes (Arias - contact issues, L Allen - BOR upside , Moss - reliever, Quant - maybe a good MOR starter but still risks,..). And as people say, most prospects won't work out. In todays time, when very few top prospects like Patino and his 60 FV (currently 13th on FanGraph board) are traded anymore, you need to capitalize on the leverage you do have like TB did with Snell (w 2-3 years on contract like Ramirez). Yes, we have a rule-5 roster crunch but if we trade Ramirez this year or next, we should land a 55 FV in Waters and a 45+/50 talent in Langeliers/Contreras at a minimum (plus more) -- if not a Pache or Anderson (top 20) type if done this year. I would gladly risk some 40 FV players in Tena, Fermin, Burgos or cut 35 FV players in Clement, Moss, Broom, Scott because as with college football not all 5 stars hit and some 3-stars will amaze but the more 4/5-stars you have the better odds you have that you will field a good team in the future.
For me, just buying a lottery ticket (long-shot odds) each year isn't good enough (yet many people do like this and thus play it each week). If we have to bite the bullet and have $60-$70 million payroll for next 2 years before going back up to $100 million range, I just don't like our chances of just having Bieber and Ramirez. If we had all of our Valera, Bracho, Jones, other Naylor and Miller prospects ETAs in 2021, that is one thing to bet on and keep Ramirez.
So, if 2 of Miller, Johnson, A Rosario or Jones shows enough in ST to handle OF/CF with 3-4 WAR potential and push Naylor to 1st, great -- we got our lineup fixed over the AAAA players of Mercado, Zimmer, Bradley, etc. Yet, Jones is starting at 3B in ST, Rosario at SS, and we are still pulling from the scrap heap of deferred players because we have little faith in Johnson/Mercado locking down their positions. I am just not confident enough.
So after June of this year, we need to see if value we have in Ramirez is better to make our fans happy in 2021 by keeping him or getting more value in 2022/23 with young players or prospects. Or, we just keep wishing that we get the next Arozarena or Yaz breakout (even though Baltimore gave up on Yaz and STL had surplus OF - gave them their rejects even though they got a great pitching prospects). However, last time we did that, we struck out in Bauers for Diaz & Sulser and only 1-3 of these trades of trades happen each year. It's hard to line up team needs especially as teams favor their prospects (that they know) over other that they just scout.