# Who is the biggest what-if in men's tennis history?

> Injuries, walk-aways and talent that never quite converted. The careers that leave you wondering.

*By YPB Team · Published August 23, 2026 · https://youpick.best/ranking/who-is-the-biggest-what-if-in-mens-tennis-history*

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## Current results (no votes yet)

1. **Bjorn Borg** — score 1000/1000
   Won eleven majors and walked away from the sport at 26.
2. **Juan Martin del Potro** — score 512/1000
   Won the US Open at 20, then lost years to wrist and knee surgery.
3. **Goran Ivanisevic** — score 512/1000
   Lost three Wimbledon finals before finally winning as a wildcard.
4. **Milos Raonic** — score 444/1000
   One of the great serves of his generation and one major final.
5. **Richard Krajicek** — score 444/1000
   Won Wimbledon in 1996 and lost years to knee and elbow trouble.
6. **Gustavo Kuerten** — score 363/1000
   Three French Opens and a world No. 1 ranking, ended early by a hip injury.
7. **Marat Safin** — score 363/1000
   Beat Sampras and Federer in major finals, and won only two titles.
8. **Nick Kyrgios** — score 363/1000
   Beat every member of the Big Three and reached one major final.
9. **Andre Agassi** — score 363/1000
   Won five of his eight majors after turning 28, having fallen to No. 141 at 27.
10. **Ernests Gulbis** — score 266/1000
   A French Open semi-finalist whose talent never settled into a career.
11. **Tommy Haas** — score 148/1000
   Reached No. 2 in the world and spent much of his prime injured.
12. **Robin Soderling** — score 148/1000
   The only man to beat Nadal at the French Open before illness ended his career.

Tags: sports, tennis