The extent to which outsiders could legally meddle with player's finances and free-agency decisions

Suppose some wealthy Washington DC tycoon didn’t want Bryce Harper to leave for the Phillies, and said “Hey I’ll pay you $500 million if you’ll stay here with the Nationals” - would that be permitted according to law and MLB regulations? (assuming there was zero communication/contact/collusion between this wealthy fan and the Nationals organization)

Technically, I don’t think that this would be any sort of violation of any of the rules that any of the major U.S. sports leagues have, though I also imagine that the league in question would want to look very closely at any relationship between the wealthy individual and the team, to make certain there was, in fact, no collusion, and that it wasn’t a clandestine way to circumvent the league’s rules about salaries.

Top-tier professional athletes get big paydays from third parties all the time (and some of them make more money from their endoresment deals than they do from their actual sports contracts), though it’s usually from appearing in advertising and endorsing products. In this case, the payment is in consideration for the player making a particular decision, but I can’t see how it would violate any laws.

If Harper ended up signing a contract with the Nationals that was below market value because of the deal, the MLBPA could veto it like they did when Alex Rodriguez signed with the Red Sox. They are determined to see that players get what they are worth so the market for player contracts doesn’t go down. The Nationals would still have to pay Harper the going rate, so Harper would get paid double.

Good point; it would have to not look like a “sweetheart deal.” But, one should note that it was the players’ association which intervened in that case, not MLB itself.

That was different though - A-Rod was still under contract to the Rangers, who wanted to trade him to the Red Sox. He was willing to take a pay cut to go to the Sox, but because he still had an active contract, the union vetoed it rather than allow the precedent of players “voluntarily” taking a pay cut on their current contract.

Harper was a free agent, not under contract to anyone - so he’s under no obligation to go to the highest bidder, and the union has no power to force him to. If a free agent wants to take the 2nd or 3rd or 5th best offer, because he likes the city/wants to keep his kids in the same school/has a favorite massage parlor nearby, etc. the union has no power to force him to accept a higher offer.

Ah, thanks for clearing that up.

DC Tycoon could also offer $500M to Harper as a lifetime endorsement deal, contingent on his remaining a DC area baseball player.

That’s a good point. In a sense, I think the scenario presented by the OP is not only possible, but is common. If an athlete signs an endorsement deal with a local business to appear in commercials and other advertising to promote a product, then that deal surely depends on their status as a player on a local sports team. If they leave the team and move to another area then their endorsement is no longer valuable, hence they are literally being paid by a third party to stay with the team.

Here’s an example. Troy Brown was released by the Patriots, but resigned with them even though he had a better offer from the Saints, because he had good endorsement deals in New England from TD Banknorth and Dunkin Donuts.

I know the OP was referring to team sports, but in pro golf, is it still common to offer certain golfers appearance fees just to play a particular tournament? Those fees are in addition to any prize money the golfer might win.

Interesting responses, thanks all. Wonder if this applies to incentives as well? Say, some wealthy tycoon now offers all Team USA players $10 million apiece if they win the FIFA World Cup, or all of the players on his favorite team $10 million apiece if they win the Super Bowl.

It appears that appearance fees are against PGA and LPGA Tour policies, but some tournaments appear to find ways around the policies (like pro-ams or “skins games” earlier in the week of the tournament). Also, touraments outside of the US tours apparently still regularly offer such fees to top golfers to attend.