I'm the same height and was north of 240 when I got back on the bike. Have him go to a Specialized dealer (or anyone else) who has the ass-o-meter and get his sitz bones measured. Then buy the most padded saddle that's 5mm wider.

Once he's dropped 20 or so pounds, he'll likely need a less padded saddle, but this is a good place to start.

A bike fitter with a BikeFit SwitchIt would be a great option for him. When it comes down to saddle comfort, there are so many variables that it's best to just try different options. Measuring the ischial tuberosities (sit bones) can help identify what saddle will help, but it's only part of the story.

We don't know what aspect of the saddle hurts your brother, other than it hurts. Cycling shorts may do more harm than good, as the thick pad is just more stuff jammed in "down there." At 300 pounds and 6', he could benefit from a lube to overcome friction issues.

Shameless plug: I do saddle testing for free, with about 75 saddles to choose from, a SwitchIt, a SQlab fit bench to measure the sit bones, and a variety of lubricants, if we really need 'em. I'm in central Indiana.

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Travis Rassat
Vector Cycle Works
Noblesville, IN
BikeFit Instructor | FMS | F.I.S.T. | IBFI
Toughman Triathlon Series Ambassador