Outstanding post, Max. 100% spot on.
Certainly, paying so much of our spending budget on players not giving us much value, if anything is a major reason for our lack of success. That is on the GM/CBO's. Not spending enough is the other major reason and that is on JH & Co. It has really been a tag team event since and including DD's final year with the Sox.
Here is a look at some of the failed big contracts by year, starting with 2019 (in $millions): 31 Price began his steep decline, 21 Porcello had a god-awful season, 17 Nate (5.99 ERA in just 12 GS), 15 Pedey (nada) and 15 Sale (4.40 in 25 GS) In some ways, the 2019 saw the biggest waste of big money contracts over a long period of time... more than any year of Bloom, Brez and maybe even Ben & Theo.
2020 was a total disaster and was Sale's first extension year (25.6M and 0 GS). Even JD 22M hit .680. 17 Nate did okay but missed 25% of his starts. 14 Pedey gave nada, 8 ERod sat out the year. The 6.5 spent on Martin Perez pales when compared to those listed ahead of him, but was still a bad choice by Bloom.
2021 was the feather in Bloom's cap, but in reality, we still saw a lot of wasted salary, including the $10M Bloom paid Richards and 5.5 on Perez. We also saw... 25.6 on 9 starts by Sale and 8.3 on ERod's 4.74 ERA. The others pulled their weight, so this was one of the better years for least amount of sunken cost, and it's no fluke, we did well.
2022 saw another 25.6 wasted on Sale's 2 GS. 17 Nate did okay but missed 12 GS, 23.3 on Story missed, badly (Bloom,) 22 JD was down at .790. The $12M spent on JBJ and 7 on Kike hurt, as well. The 9 Barnes extension fell apart mid season. (Bloom did okay with the Wacha, Hill, Strahm and Renfroe deals)
2023 saw yet another letdown by 25.6 Sale w only 20 GS and a not-so-great 4.30 ERA. 23.3 on Story was another year missed. Bloom's 18 on Yoshida, 10 on Kluber and 10 on Kike were near or total busts. (Bloom did okay with themis to lower deals like 16 Jansen, 11 Turner, 7.5 Martin & 7 Duvall.
2024 saw a frighteningly low amount of additions, especially large ones. Brez's 19.5 on Gio was a complete wiff. Paying 17 for Sale to win the Cy Young w ATL was worse than a total bust. 23.3 on Story (Bloom) was yet another wasted year. 18 on Yoshi looked a little better, but he missed time and still has not earned his contract for 2024, alone. 16 on Jansen was okay, 7.5 on Martin was not. (Only the 6 paid for O'Neill and 1 for Criswell worked out well.) 5 Hendriks gave us zero for 2024.
I'm not going to total all this up, but it has been a huge percentage of our budget.