I don't know man, I think the pain and regret of watching your franchise player, who you've followed since A ball, dominate a few years for someone else is much worse. And throwing a ton ton of money at another FA who comes in and hits a cliff in a year is shittier than getting the same outcome with "your guy."
The Yankees did well to just pay the man and keep him. They're a big market franchise who also have the ability to build up a great farm. The Pujols contract gets cited a lot but what's left out is that the Angels have also been fucking atrocious at building a farm system. That's the reason they could never survive the Pujols (and Rendon) contracts.
I understand the signing because of the Yankees' budget, his celebrity/popularity, and the lack of viable alternatives. And, there have been a number of players who have put up really good numbers through their 30's, like Edgar Martinez, Hank Aaron, Paul Molitor. Even guys like Fisk, Yaz, Nelson Cruz and Big Papi show some reasons for optimism looking at Judge's potential production for his age 31-39 seasons.
Baseball-Reference lists Brian Giles, David Justice, George Springer, Jason Bay, and Ryan Howard as Judge's most similar batters through age 30. That's a mixed bag looking ahead.
And, the Pujols comparisons are hard to avoid. Here are their FWAR totals leading up to their age 31 seasons:
Age Pujols Judge
25 7.7 8.7
26 8.1 5.3
27 7.7 4.3
28 8.7 1.1 (2020)
29 8.4 5.5
30 6.8 11.4
Based on those numbers, at age 31, I'd say that Pujols was a "safer" bet to produce through his age 39 season.