If he’s never participated in the pool, he probably shouldn’t get a share. If it’s a one-off miss then he should. A huge win divided by 12 vs it divided by 11 is a minimal difference. You’d each earn that back in interest alone within a year.
I’d base my decision entirely on how we anticipated Jerry might feel for missing out. If he didn’t care, no worries, see ya Jerry. If he was disappointed and would lose his job now we were all retiring, that might make a big difference.
I would tend to go along with the group on this but would resist giving him a full share. If Jerry can come out of this richer by somewhere between 100K and one million bucks then I’d be good with this. If the majority of the group wanted to tell him to take a hike, I’d probably toss him a couple years salary on my own initiative.
One this I have not seen mentioned is what to do with the owner. I’m of the opinion that whatever Jerry gets should also be given to the owner. He’s been fair with us and we’ve enjoyed working there. Our inevitable departure is going to cause him some degree of disruption to his business. I certainly wouldn’t offer a full share but why shouldn’t the owner get some degree of a payday from this?
No way do I give him a full share, not even remotely considering it. However, in the spirit of kindness, I would endeavor to convince my co-winners to pony up $50-100k each to net Jerry a nice boost to his retirement nest egg.
P.S. This was a plot line in the TV show Windfall, about a group of friends who decide to buy a bunch of lottery tickets while they’re at a house party, and wind up winning. IIRC, it was the hostess of the party who didn’t pitch into the ticket pool, so they had a bit more of an incentive (“We never would have even bought the tickets if she hadn’t thrown the party”) to include her.
I would buy his mortgage note and change the terms to 0.05%, with no late payment fee (pay what you can when you can, it is going almost entirely to the principle). That would at least take a lot of pressure off him.
The most I’d give him is the current max yearly amount of the gift tax, because I’m too lazy to do the bookkeeping otherwise. If everyone from the office pool did that, he’d have a few hundred thousand for his non-troubles. I might not do even that, though, I’m not sure.
I don’t actively DISLIKE EVERYONE I work with, but after my last day of work (for whatever reason) I don’t expect to see ANY of them again.
I like to think I’d be extremely generous if I were wealthy. Towards my friends, family, and individuals/organizations/causes I thought worthwhile. But I don’t see any reason to extend that generosity to Jerry.
I get that the office bought tickets as a group, but Jerry chose not to participate and is now in the same group as everyone’s close friends, children, spouses, close family, distant relatives, random strangers.
So whatever the individual winners want to give him is up to them.