by TK Focht, Tanis O’Connor, and Josh Oratz
Answer: CHASE UTLEY
Problem: Valentine’s Day Town/​Arbor Day Town

This puzzle is a criss cross with an added constraint based on its dataset—the nicknames players wore during the 2018 Major League Baseball Players’ Weekend, when MLB players chose their own nicknames for their jerseys and wore uniforms in styles reminiscent of Little League. The dataset is hinted at in the flavortext and through the puzzle’s title. (Bootsie is Ian Kinsler’s Players’ Weekend nickname.)

The full list of names and colors is on MLB’s website.

Each of the marked junctions is a crossing of two players from the same team (as of 2018 Players’ Weekend), and each team is represented once; the Dodgers and the Red Sox are provided to get solvers started. Spaces are removed from names, but punctuation is “regarded,” as noted in the puzzle. There is only one unique way to fill the grid according to this constraint.

W
I
L
D
MHLAD
D.MOUNTAIN
RR
OS
MGESWEETSWINGIN'
AEMINUOAKQ
MILYLURCHBGSEAU
KINGCOBRASBIGMAPLEE
SDSIRPUGRA
SPINRATE-ONPFPHIK
AFDTBIGGERFELLAY
NLDECARILL
GACNPOLLOL
YNCNYMRBA
DCINQUARTERRICANUTLAA
ELLLANERONADCTEXBSHOWTIME
RDSPAGHETTIE
SEMNEGM
FRIICWSFA
IPMANOFSTEALUEC
EASFIHDSH
LLASTNAMEDHSHOUGTI
ADKTIOCTHEDRAGON
ESYSCRRTBHRAE
LWPHAMTASTICITORT
EAUCOLYELBRINGEROFRAIN
CKATLLETTUCECBOSLGS
TROCKKBROCKSTARBPB
RAENAEEHSI
IKNYYRAIREAETG
PICKLESZGGLCHCNREAWSH
INTSPEEDPASSFEDDECCINI
DYAILKG
ABALELNIÑOIAU
DILLYKCTANSS
DDETTCLEGA
THEPLUMBERDIRTBAGEUMIA
UOSTLRALLSTARLIN
WACHAMOLEU
EISS
NU
AP
TEPIT
FLACOFUERTE
RN
O
V
A

Each of the teams’ crossings can be matched with one of the jerseys at the bottom of the puzzle, which match the uniform colors from Players’ Weekend. Not all of the color combinations are unique, but each is unique within its division, and all divisions can be identified. This allows placement of every marked crossing letter in a specific position.

H TEX E HOU S OAK H LAA A SEA
R MIN E DET S CWS A CLE N KC
D BAL E NYY R BOS S TB O TOR
N SF C COL O LAD O ARI P SD
E CIN R PIT S CHC M STL O MIL
N WSH I NYM K ATL E PHI R MIA

The cluephrase HE SHARES ANDERSON COOPER’S MONIKER indicates that the answer is the player wearing SILVER FOX, the Los Angeles Dodgers’ CHASE UTLEY.