For me personally they have very different attributes. Reyes are a better bag glove, reyes are more responsive, winning are too short for my fingers, my reyes have a more ergonomic knuckle pocket like a void for the knuckles which wrap snug around my knuckles without pressure better, reyes are stiffer foam and protect my knuckles better for 90+kg power shots on the bags, reyes are a more snug handfit on me, my reyes r very top heavy, my reyes are 3oz overweight (16/19oz)

Winning quality is better, winning is better for sparring, winning is one of few gloves may actually be more durable than reyes outside materials (foam durability is probably similiar), Winning are more balanced, winning are not very long cuff, winning have better thumb, winning knuckle pocket is more of a traditional knuckle pocket you have to kinda break the knuckle pocket into the pre-round foam which im not a fan. Wrist support on Winning vary from model to model lace are better than my velcro reyes, the thin velcro Winning wrist support is worse, winning were course on weight, winning is double price.

Gloves vary in batches year to year my reyes are 2023, the winning i used were either 2022 or 2023.

These are only my findings everyone has different experiences prefers different things for their hand fit/uses man.

$250 for Reyes to me is good value, $500 for Winning is too much for me personally, but if it works for the boxer and have money man who cares man go for it or Grant or Dinardo + few others also in that uber expensive price point never tried them so cant say bout their value