The problem is that winter water arrives all at once and doesn't stick around. When it rains a lot in a short time, especially in areas like Castilla with clay and compacted soils, the water either runs off into watersheds (and goes elsewhere) or evaporates quickly. It doesn't infiltrate the subsoil enough to create reserves that keep the land hydrated throughout spring and summer. It's like if you filled a glass all at once: half of it spills.
What makes it worse is that the months from May to September are increasingly dry and brutally hot. I visited some friends recently who have a small vegetable garden in Toledo and I was surprised how much water they needed to pump in June so nothing would die, despite having decent rain four months before. The soil really dries out, the subsoil gets depleted, and the aquifers don't refill the way they used to.
Your grandfather is right to see it as especially serious. The thing is, you don't just need rain in winter - you need it distributed over time and then to maintain some moisture during the warm months. A drought like the one in 2026 happens when the balance breaks: concentrated winter + scorching spring and summer + less water infiltrating the ground = disaster for crops and livestock.