Do they really expect me to play baccarat with Count Dracula?

I'm having a hard time figuring out how to make the Gambling skill in Night's Black Agents interesting in play, without breaking the game in any way.

It hasn't really mattered in my previous two campaigns, because no one ever put more than a couple points in it. This campaign, I've got 2 PCs with level 8 Gambling ratings, and while there's some interesting "Cherries" to pick from at that level, it's hard to picture how I'm going to make Gambling be important (or interesting) often enough to make those points feel well-spent.

I guess the right play for the GM is to craft the narrative so the PCs have no stable income and have to rely on periodic Gambling forays to finance their Ops. The game's monetary system is pretty loosy-goosy and avoids dollar signs as much as possible. There's no equipment charts, nor do you have to account for every last gold piece, so there's no mechanical incentive (or method) for, say, making a 20% return on investment. Either it does nothing, or it generates "Excessive Funds" with no real risk, so the needle jumps wildly between "useless" and "broken" depending almost entirely on GM fiat. I'm not happy with that.

What's more, the game's mechanics are set up to encourage PCs have rock solid competence. If you know the difficulty of the roll you're making, and success on the roll is at all important, the right call for the player is almost always to spend enough points that the die is irrelevant.

The only likely reason not to spend enough that even a "1" on the die is a success, is if you're trying to hold something back for later in the session. It's easy to imagine situations where a PC might not want to spend their last point of Shooting, or Driving, to hold on to it in case another gunfight or a chase scene breaks out. But you're rarely if ever going to think "I'd better not spend my last point of Gambling, just in case there's a surprise slot machine ambush!"

If I make all their gambling be one or two high-difficulty rolls, the PC will dump all their points on them and be guaranteed to win big. Calling for a long series of smaller rolls might make the PC's decisions from roll to roll feel more important, and better justify (via hard work) the benefits of gambling-as-finance, but it's probably going to put the uninvolved members of the party straight to sleep. Either way, the rules as written don't really catch the feel of risking everything on a big bet, which is a real shame because that's the appeal of a gambling montage in a spy movie. I suppose you could get that feel by setting really high difficulty numbers, I guess, but then you're looking at a situation where a PC drops 8 or more points on a single roll (which would be overkill on any other skill) to still only have a 50-50 shot at success. More exciting, yes, but again it would feel like those 8 points during Character Creation could have been spent better elsewhere.

I'm starting to think that maybe Gambling should be an Investigative Skill, not a General Ability, in Night's Black Agents. If that were the case, you'd use Gambling to qualify or earn a seat at the table where the Enemy high-rollers were playing, or to locate the floating poker game where the opposition thugs play. Gambling would then pick up clues about NPCs using sleight of hand, or NPCs having suspiciously good luck, or you'd use Gambling to follow the paper trail of the mafioso who owns the track. You'd even be able to spend Gambling to gain a Tactical Fact-Finding Benefit or Tag-Team Tactical Benefit bonus on a skill roll, and retroactively justify it in the narrative as having spent your winnings to have better equipment. (Gambling spent to TTTB on your comrade's Preparedness roll just seems kinda fun.) There's some decent ideas there, so I'm going to try to work some Investigative Spends for this General Ability in my current campaign. It's going to take some significant scenario-design effort on my part to make those 8 points feel as meaningful as they would have been if sunk into Athletics or even Digital Intrusion.

Next campaign, I'll probably shift Gambling to the other column of the character sheet. It seems like that's where it belongs.

If anyone with GUMSHOE experience has any better ideas or advice, I'd love to hear them.