After putting a little more thought into this I confirmed that the Kelly formula does indeed turn out to be the optimal wagering strategy in this case. The key is that it calls for betting a fraction of your
current bankroll, not of your
original bankroll, so you never really run the risk of ruin, at least not in theory anyway.
I ran a small simulation under which wagers are made only on the rare situation’s like Saturday’s Tenango example, where you have a +100% edge on a 50/50 proposition calling for a Kelly bet of one third of your bankroll. I looked at what would happen if you had a really horrific start and lost the first 6 bets in a row (an extremely unlikely 1.5% chance of occurrence), followed by a more normal 50% alternating win/loss sequence for the next 50 wagers. With a tiny initial bankroll of $1,000, ignoring the effect on the pool, the results would look like this:
1) Wager $333. Lose. Balance: $667
2) Wager $222. Lose. Balance: $445
3) Wager $148. Lose. Balance: $297
4) Wager $99. Lose. Balance: $198
5) Wager $66. Lose. Balance: $132
6) Wager $44. Lose. Balance: $88
7) Wager $29. Win $87. Balance: $175

Wager $58. Lose. Balance: $117
9) Wager $39. Win $117. Balance: $234
10) Wager $78. Lose. Balance: $156
11) Wager $52. Win $156. Balance: $312
12) Wager $104. Lose. Balance: $208
13) Wager $69. Win $207. Balance: $415
14) Wager $138. Lose. Balance: $277
15) Wager $92. Win $276. Balance: $553
16) Wager $184. Lose. Balance: $369
17) Wager $123. Win $369. Balance: $738
18) Wager $246. Lose. Balance: $492
19) Wager $164. Win $492. Balance: $984
20) Wager $328. Lose. Balance: $656
21) Wager $219. Win $657. Balance: $1,313
22) Wager $438. Lose. Balance: $875
23) Wager $292. Win $876. Balance: $1,751
24) Wager $584 Lose. Balance: $1,167
25) Wager $389. Win $1,167. Balance: $2,334
26) Wager $778. Lose. Balance: $1,556
27) Wager $519. Win $1,557. Balance: $3,113
28) Wager $1,038. Lose. Balance: $2,075
29) Wager $692. Win $2,076. Balance: $4,151
30) Wager $1,384. Lose. Balance: $2,767
31) Wager $922. Win $2,766. Balance: $5,533
32) Wager $1,844. Lose. Balance: $3,689
33) Wager $1,230. Win $3,690. Balance: $7,379
34) Wager $2,460. Lose. Balance: $4,919
35) Wager $1,640. Win. $4,920. Balance: $9,839
36) Wager $3,280. Lose. Balance: $6,559
37) Wager $2,186. Win $6,558. Balance: $13,117
38) Wager $4,372. Lose. Balance: $8,745
39) Wager $2,915. Win $8,745. Balance: $17,490
40) Wager $5,830. Lose. Balance: $11,660
41) Wager $3,877. Win $11,661. Balance: $23,321
42) Wager $7,774. Lose. Balance: $15,547
43) Wager $5,182. Win $15,546. Balance: $31,093
44) Wager $10,364. Lose. Balance: $20,729
45) Wager $6,910. Win $20,730. Balance: $41,459
46) Wager $13,820. Lose. Balance: $27,639
47) Wager $9,213. Win $27,639. Balance: $55,278
48) Wager $18,426. Lose. Balance: $36,852
49) Wager $12,284. Win $36,852. Balance: $73,704
50) Wager $24,568. Lose. Balance: $49,136
51) Wager $16,379. Win $49,137. Balance: $98,273
52) Wager $32,758. Lose. Balance: $65,515
53) Wager $21,838. Win $65,514. Balance: $131,029
54) Wager $43,676. Lose. Balance: $87,353
55) Wager $29,118. Win $87,354. Balance: $174,707
56) Wager $58,236. Lose. Balance: $116,471
Comparing the Kelly results to other wagering strategies under this same scenario:
1) Kelly(33% of current bankroll): Min Balance: $88. Final Balance: $116,471
2) Betting 5% of current bankroll: Min Balance: $734. Final Balance: $6,699
3) Betting 2% of current bankroll: Min Balance: $886. Final Balance: $2,288
4) Flat Bet of $50 on each race: Min Balance: $700. Final Balance: $3,200
5) Half Kelly (16.5% of current bankroll): Min Balance: $335. Final Balance: $88,641
Even with an almost impossibly horrendous beginning where you lost over 90% of your original bankroll, you still would come out vastly farther ahead in just 50 bets using Kelly. Other percentage or flat betting strategies don’t even come close.
Although it can be extremely volatile, full Kelly is clearly the optimal course of action
if you have tested the performance of your overlays and are sure your edge is what you think it is.
The benefits of \"half-Kelly\" are also clearly evident. It captures much of the upside of full Kelly, while greatly reducing the volatility and max drawdown, thereby providing somewhat of a cushion for misjudgements in perceived overall edge or final odds, which is why so many practitioners use it rather than full Kelly.
The other thing to note is how quickly you reach pool size limitations when you have such a big edge like this. With a more typical edge like +10% to +25%, the swings would be much more moderate and it would take much longer to reach pool size limitations.