Let’s take a look at some stats first
Roddick:
493-167, .747 overall
23-49, .319 vs top-5
Medvedev:
385-152, .712 overall
17-38, .296 vs top-5
Medvedev has an extra slam final and 1 extra Masters title. He also has a WTF title. Also, Medvedev has 5 YE rankings in the top-5 to Andy’s 3. However, Roddick has a much better career winning pct, despite playing through a long decline period. Roddick also has a YE#1. And that was well earned, since he won the North American triple(Montreal, Cinci, USO) in a very impressive fashion. Note: includes beating Federer in the semis of Montreal, which seemed to spark Andy. Federer, Djoker, Agassi, and Sampras never won the North American triple. IIRC, Andy received an extra million bucks for his stellar North American swing.
I see an argument for both players. But I have to give this one to Roddick for the win. However, Medvedev could pass Roddick. Let’s see what the rest of his career brings him. He’s not done yet. Another slam title, or another WTF title, or 2 more Masters titles, or 1 more top-5 YE rankings, or 2 more YE top-10 rankings would do it. He doesn’t need to do much to pass Roddick. It’s close.