Drake certainly could and did win in the East. But the initial question posed by Jimbo was who would win a KHJ vs. WABC battle in the same market. I'm assuming we're not bending timelines and that WABC would begin in 1960 and KHJ in 1965.
My answers remain...in L.A., WABC would have been old news (maybe older with KFWB having done personality top 40 two years longer, beginning in '58), and KHJ would have wound up the winner.
In New York, KHJ would probably have not been able to overcome WABC's head-start and listener loyalties. Most likely, it would have split the WMCA listenership and allowed WABC to be king of the hill sooner (ironically the same thing Drake's K-100 did in Los Angeles in 1974, splitting KKDJ's audience, allowing KHJ to stay on top despite declining shares and delaying the rise of FM Top 40 in that market).
Something to consider (and this is from someone who's a big Drake fan): Bill Drake never won a battle against an established competitor with a vastly better signal, except one: San Diego, where KGB (5kw at 1360) knocked off 50,000 watt KCBQ (1170). And the Q was highly directional at night, which affects some of your morning and afternoon drive a third of the year.
In L.A., KRLA (1110) was 50,000 watts, but had issues, and KFWB (980) was 5,000 watts like KHJ, with a similar dial position. And KRLA had weakened KFWB but had not yet risen to dominance (as The Real Don Steele said: "The joint was ripe.")
San Francisco: KEWB (5 kw at 910) was just about over and KYA had an inferior signal (5kw at 1260) to KFRC's 5,000 watts at 610 with the towers virtually in the bay.
Boston: WBZ was already on their way to Adult Contemporary, leaving WMEX down at 1510 on the dial. Easy pickin's for WRKO at 680.
Detroit: WXYZ at 1270 and WKNR at 1310. CKLW was already Top 40 with a monster signal. Drake just refined it and won.
Point is, none of those stations that had their tails handed to them by Bill Drake had the advantages of WABC. Again (among other reasons), probably why RKO didn't give him WOR-AM.
---Michael Hagerty