The semitragic history of this puzzle is brief—a New York Times rejection last Spring, with a note that solvers would not readily equate an "O" with a RAIN DROP in each of the four down theme entries. Hard to argue with that, but I still enjoyed creating this puzzle, and trying to have fun with it.
I saw the puzzle, physically, as the roof of a house—we're looking down on it, seeing LEAKY_ROOF along the ridgepole, and four "leaks" scattered about [asymmetrically—just like real leaks!].
In the photo, you see our house under construction in the Spring of 2012, on a tidal cove in Midcoast Maine (So. Thomaston), with sandwiched 2x12s as the ridgepole. Our house is enormously well-insulated and very dry—no leaks—but other houses aren't so well built. Hence the puzzle.
I made two versions of the puzzle, before continuing the process with George and his team. One has OIL(O)PRICES at 30-Down, while in the other, this entry is replaced by GAS(O)PRICES. I prefer the latter, since the "O" in OIL disrupts theme consistency [none of the other themers has an "O," except for the "drop"]. This change forced an overhaul of the NE corner, resulting in one "Natick" of an entry, Broncos' former star lineman Tom NALEN [replacing the former partial, A_NAIL]. I suppose there might be another NE solution, but the ANCHORS, BALONEY, BLITZEN stack appealed too much to me.
The revised version incorporates several changes, all thanks to comments I've received and George's editing and input. Comments were a huge help—PAOLO, ROK, ROCCO, STONERS, ASHCAKE, and TEAC from earlier drafts have all been replaced. I'm still not fully impressed with "DROP-in CLINICS" which reads CLINIC(O)S in the answer grid. Where the "O" fits cleanly between two parts of an entry in the other three themers, the "O" placement here feels arbitrary in a word that doesn't "break" cleanly.
So with further prodding, I pursued yet another version, using "DROP-in-DAY CARE" which Googles nicely ("Handy option for a toddler's parents") and is entered into the grid as DAY(O)CARE. As of a few days ago, I had all new fill in the NE, with one pretty ugly word that I was still trying to repair. A final intense back-and-forth push with George, covering several days including the weekend, resulted in the final final version found on this puzzle's main page, and yet another version.
The key to making the DAY(O)CARE versions work was to identify 20-Across. In the version that uses GLAMORISE (British spelling), ATMAN at 7-Down is the weak sister [despite several Shortz-era hits], but I feel that it's slightly better than Tom NALEN in the original grid. In the second alternative, FLY_NO_MORE seemed to me a 9-letter partial (unacceptable in my book), until we discovered RAF test-pilot Brian Davies' memoir of the same name. It's still a bit Natick-y, but gettable through the Down crossers and a measure of inferential common sense. I do think either grid is a big improvement over the old CLINICS version.
In the last year or so, I've tilted more toward themed puzzles, away from themeless, and have been aiming more for "smile value" instead of construction virtuosity. Too bad this one didn't make the cut at the Times, but I'm sure we all have those stories to tell.
GB adds: It's a pleasure to be able to provide a home to this quirky theme, and to synchronize its posting with Ned's themeless puzzle published on the same day. I enjoyed working with Ned on tweaking both the fill and the clues, and the no-holds-barred suggestions from our vaunted beta testers (listed on the puzzle's main page) contributed to an improved version that we hope solvers will enjoy! Of course, it would have been nice to have no other O's in the puzzle, beyond the four theme answers and the DROP reveal, but one can't have everything.
I think that the disparity in home run production between twin brothers and one-time teammates 64-Across must be some kind of record, 462 regular-season for Josˇ, and 0 for Ozzie. I also found it amusing that ST_CYR is considered the French equivalent of the USMA, so we had to clue the former word for the burlesque queen instead. ARMY_ONE was the helicopter that transported private citizen Richard M. Nixon off the White House premises after the dramatic events of August 1974. Finally, I would like to thank Ned for calling to my attention pioneering confrontational talk show host JOE PYNE [of many YouTube clips readily available, I found this one to be particularly fascinating].