The following are some examples of what can be categorized as goodwill.
Brand or trade name recognition
Websites, Domain names
Trade Secrets, recipes
Customer list, Exclusive supplier list
Copyrights, Trademarks, Patents
Licenses, permits, regulatory approvals
Proprietary Designs, Proprietary Know-How
Customized or Proprietary Databases
Published Articles or Industry Press
I'd guess goodwill factors into both Rory Mcilroy Inc (he's likely incorporated himself) and his business ventures. Rory's goodwill is mostly made up of reputation, branding and contracts. His businesses would also reflect his reputation and brand along with the other items.
If his golf performance declines I'd expect his overall value would also decline given much of his goodwill comes from his golf as he's not yet achieved the celebrity status Tiger Woods has.
I usually give them a snide remark or two. Some get it, a few don't. Once an old guy was belittling me about using a colored ball after the round. A total stranger and a poor golfer - worse than my bogey golf. The guy was so out of touch that I didn't think he'd get my hint.
I understand the concept of Goodwill. My question is how did the intangible get generated
In your example, the Habs have been sold to various owners, most recently to back to Molson. Molson's purchase price probably was for more than could be allocated to specific assets (like cash accounts, receivables, fixed assets). The excess is booked to Goodwill. See, it was the sale's proceeds that gave rise to the asset.
In Rory's case, how did the intangible actually arise? This, apparently, was a corporation he set up himself to handle his various business activities. If this number is supposed to represent revenue to be generated in the future (supposing all goes well), it seems like improper revenue recognition.