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My friend has a great vocabulary but is also quote humble.

Every time we play Scrabble he wins easily. He says he tries his best, with one exception:

  • If the opportunity ever arose, he would never play the highest possible scoring move in the game of Scrabble, because he thinks that would be "showing off
  • If multiple Scrabble moves have the same maximum possible score, he would consider them all tied for 1st and only be willing to play the next highest

Using standard Scrabble rules and a standard dictionary what would be the highest scoring play my friend would be wiling to make in a game?

Count no only the letters values of highest scoring word but also:

  1. All secondary words created during the turn
  2. All the maximum possible bonuses based on the location of the words earning a score.

Edit: Although I believe the problem can be "solved" if some basic assumptions are made regarding the need to use certain bonus squares thereby severely restricting the number of possible (primary) scoring words to be played, I have made the question open ended in case there is room for further improvement.

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    $\begingroup$ This looks like quite the task. Do you believe you have the correct answer? $\endgroup$ – Roland Jun 13 '16 at 2:02
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    $\begingroup$ The open-ended tag is probably appropriate until someone can prove an absolute maximum $\endgroup$ – humn Jun 13 '16 at 5:30
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    $\begingroup$ +1 because there is a lot of interest in questions such as "what's the highest possible score in Scrabble for a) a turn b) the whole game?", and because, as far as I know, this particular question is original. $\endgroup$ – Rosie F Jun 13 '16 at 8:29
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As a baseline answer:
1780 points from this placement of oxyphenbutazone, or if this is somehow proven to be the best with an English standard dictionary, without the circled "S" for 1779 points.

enter image description here

Since there is a lot of confusion over the wording of the puzzle, I'll give my interpretation:

  • By "highest possible scoring move in the game of Scrabble", I understand that this player will consider any move that is not equal to or tied with a record score. The alternative is that he avoids the best possible move each turn, which means there are myriad avoided scores ranging from as low as ~20 to as high as a record move.

  • The puzzle does not say "what is the highest scoring move my friend would make, given the opportunity to make the highest scoring move". It asks "what is the highest scoring play my friend would be willing to make", which by the above logic, is any move that is not the highest possible in the game of scrabble.

  • I've also assumed for now that the OP's friend is playing in North America, and is thus using the TWL dictionary. The highest score using the Sowpods dictionary would be higher than with TWL.

See this site for further exploration with non-standard dictionaries.

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    $\begingroup$ This doesn't answer the question. The two situations you describe (with and without that S) denote identical plays on slightly different boards. What we need are two different plays, scoring differently, from the same rack on the same board. $\endgroup$ – Rosie F Jun 13 '16 at 8:16
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    $\begingroup$ @RosieF It says he would never make the highest possible scoring move in the game of Scrabble, and this is not one of them, so it is valid, correct? I'm sensing ambiguity in the use of "possible". Does the OP mean in any Scrabble game ever or for each turn with the current board and rack? $\endgroup$ – Roland Jun 13 '16 at 12:58
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Extension on Roland's answer:

Hypothetical Records
NOTE: These hypothetical records were established before the introduction of OSPD 4 and have not been update for OSPD 4.
Highest Single Play
1,778 points: OXYPHENBUTAZONE, found by Dan Stock (OH) in 1996
Other words formed were (O)PACIFYING, (Y)ELKS, (P)REInTERVIEWED, (B)RAINWASHING, (A)MELIORATIVE, (Z)ARFS, and (E)JACULATING.

SOW PODS record
1,790 points, BENZOXYCAMPHORS
Highest Single Play Using Any Dictionary
2,069 points?, SESQUIOXIDIZING, found by Josepha Heifetz Byrne (CA)

Byrne found this play in 1982 using words from unabridged dictionaries. The word itself is from her own book Mrs. Byrne's Dictionary of Unusual, Obscure, and Preposterous Words The word isn't found in that form in any standard unabridged dictionary, though the OED lists SESQUIOXIDIZED and SEXQUIOXIDIZATION.

If we only allow words that actually do appear in standard dictionaries, then BENZOXYCAMPHORS for 1,962 points - found by Darryl Francis, Jeff Grant, and Ron Jerome c1986 may be the record.

From this source pg. 68.

However I do not think that this can really be considered a puzzle then, since it's more just trivia.

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    $\begingroup$ The question is about the second highest scoring play on a particular board. It wouldn't necessarily involve any of these record examples. $\endgroup$ – user21939 Jun 13 '16 at 10:58
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Here's one to give a rough idea of how high a score is possible:

a: AFILQUY 8D QUALIFY +114 114
b: EGINR 8B RE.......ING +29 29
a: ENOR G4 ENRO. +6 120
b: DEIMRX 4B REMIX.D +38 67
a: EIN H1 NIE. +15 135
b: ACGHIKL 1B HACKLI.G +71 138
a: ?EU 2A UEy +15 150
b: AERS 3B ARES +27 165
a: ?DEELOR B7 E.E +3 153
b: HIN A5 HIN +8 173
a: Y 9A Y. +5 158
b: APSW J8 .AWPS +21 194
a: AEEGMT 12D GAMETE. +22 180
b: OO 12B OO....... +12 206
a: ADFJSTT 11A AT +4 184
b: OO 13A OO +5 211
a: N A13 .N +2 186
b: ORT H12 .ORT +12 223
a: AIL 15F LA.I +4 190
b: ACJNOSU 15B JACU....ONS +74 297
a: ?ELPRSZ A1 S.LP...p.R.Z..E +1502 1692

That is, the high-scoring player plays

SULPHINPYRAZONE for 1502 using a blank for a P. Now he could have placed the P tile on the triple-word square A8, but instead places the blank there and the real P at A4. I'm sure other people can squeeze a few more points (or a few 27s of points) out of this.

The board after the high-scoring play is

A B C D E F G H I J K L M N O 1 S H A C K L I N G . . + . . # 2 U E y . . * . I . * . . . = . 3 L A R E S . + E + . . . = . . 4 P R E M I X E D . . . = . . + 5 H . . . = . N . . . = . . . . 6 I * . . . * R . . * . . . * . 7 N E + . . . O . + . . . + . . 8 p R E Q U A L I F Y I N G . # 9 Y E + . . . + . + A . . + . . 10 R * . . . * . . . W . . . * . 11 A T . . = . . . . P = . . . . 12 Z O O G A M E T E S . = . . + 13 O O = . . . + O + . . . = . . 14 N = . . . * . R . * . . . = . 15 E J A C U L A T I O N S . . # A B C D E F G H I J K L M N O

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Here's one way to adapt the high-scoring word

OXYPHENBUTAZONE to answer the OP.
a: AGHINSW 8F WASHING +82 82
b: AINR 8B RAIN....... +19 19
a: ?AEERS B3 ERASE.s +8 90
b: Y 3A Y. +5 24
a: H 5A H. +5 95
b: EKR 6B .KER +8 32
a: N 7A N. +2 97
b: ATU A9 UTA +4 36
a: OOT B11 TOO +5 102
b: NO A13 ON +4 40
a: DEEI H4 IDEE. +7 109
b: AFL 4F AL.F +7 47
a: DEEIQU 4B .EQU....IED +96 205
b: FIL F1 FIL. +9 56
a: ACIPY 1B PACI.Y +19 224
b: GIN 1B ......ING +60 116
a: EELV I8 .ELVE +12 236
b: AEGMOST 12B .OGAMET.S +76 192
a: ORT H12 .ORT +12 248
b: AIL 15F LA.I +4 196
a: ACJNOSU 15B JACU....ONS +74 322
b: ?BEOPXZ A1 OX.P.E.B...Z..e +1738 1934

That is, the high-scoring player plays

OXYPHENBUTAZONE using a blank for an E. Now he could have placed the E tile on the triple-word square A15, but instead places the blank there and the real E at A6.

The high-scoring word scores

1738 and produces the following board: A B C D E F G H I J K L M N O 1 O P A C I F Y I N G . + . . # 2 X = . . . I . . . * . . . = . 3 Y E = . . L + . + . . . = . . 4 P R E Q U A L I F I E D . . + 5 H A . . = . . D . . = . . . . 6 E S K E R * . E . * . . . * . 7 N E + . . . + E + . . . + . . 8 B R A I N W A S H I N G . . # 9 U s + . . . + . E . . . + . . 10 T * . . . * . . L * . . . * . 11 A T . . = . . . V . = . . . . 12 Z O O G A M E T E S . = . . + 13 O O = . . . + O + . . . = . . 14 N = . . . * . R . * . . . = . 15 e J A C U L A T I O N S . . # A B C D E F G H I J K L M N O

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If one is playing against an exceptionally cooperative opponent who never challenges any words, no matter how outrageous, I think the maximum would be 2449 when playing against a single opponent. Showing just the tile values, one would start with the rack 10 10 8 8 5 4 4 and the board:

- 4 - - 4 4 4 - 4 4 4 - - 4 -  = 8 tiles
3 0 1 1 1 - 1 3 1 - 1 1 1 0 3  = 13 tiles
3 - 1 1 - - - 3 - - - 1 1 - 3  = 7 tiles
3 - 1 1 - - - 2 - - - 1 1 - 3  = 7 tiles
2 - 1 1 - - - 2 - - - 1 1 - 2  = 7 tiles
2 - 1 1 - - - 2 - - - 1 1 - 2  = 7 tiles
1 - 1 1 - - - 1 - - - 1 1 - 1  = 7 tiles
1 - 1 1 - - - 1 - - - 1 1 - 1  = 7 tiles
1 - 1 1 - - - 1 - - - 1 1 - 1  = 7 tiles
1 - 1 1 - - - 1 - - - 1 1 - 1  = 7 tiles
1 - 1 - - - - 1 - - - - - - 1  = 4 tiles
1 - - - - - - 1 - - - - - - 1  = 3 tiles
1 - - - - - - 1 - - - - - - 1  = 3 tiles
1 - - - - - - 1 - - - - - - 1  = 3 tiles
1 - - - - - - 1 - - - - - - 1  = 3 tiles

Filling in the top row, with the two ten-point tiles on the double letter scores, would yield a total score of:

  • 2727 - The main word would be 20+20+8+8+5+4+4+4+4+4+4+4+4+4+4 times 27 (2727)
  • 180 - Side vertical words would be 8+3+3+3+2+2+9 times 3 (90+90)
  • 156 - Center vertical word would be 5+3+3+2+2+2+9 times 3 (78+78)
  • 58 - Two vertical words would be 20+9 (29+29)
  • 27 - Last two vertical words would be 4+9 and 4+10 (13+14)
  • 14 - Opponent's hand would score 7 times 2 (14)
  • 50 - Bingo would score 50

A total of 3212 when playing against a single opponent. For each additional opponent, move seven single-point tiles from the bottoms of the short columns to gain seven more points. I think the maximum possible number of tiles one can score with on a single play while achieving anything close to this score is 94, since four single-point tiles and two blanks must be used to connect across six of the eight columns where scoring is not possible.

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