25 entries under shrewd topic. ×

24
crafty(noun, adjective, smooth, negative, cunning)
20
sly(noun, adjective, smooth, negative, cunning)
16
cunning(adjective, negative, deceitful, devious)
15
wily(adjective, smooth, sharp, negative, cunning)
12
scheming(adjective, negative, deceitful, tricky)
10
conniving(adjective, negative, deceitful, wily)
8
calculating(adjective, negative, deceitful, tricky)
4
guileful(adjective, smooth, sharp, negative, deceitful)
3
astute(adjective, scheming)
3
contriving(adjective, scheming, manipulative)
2
canny(adjective, smooth, sharp, devious)
2
manipulative(adjective, negative, deceitful, wily)
1
politic(scheming, manipulative)
1
sharp(smooth, deceitful, devious, wily)
1
wary(smooth, sharp, devious, scheming)
0
careful(scheming, manipulative)
0
cautious(scheming, manipulative)
0
chary(scheming, manipulative)
0
circumspect(scheming, manipulative)
0
considerate(scheming, manipulative)
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APASmart Define. (2016). machiavellian thesaurus. Retrieved October 1, 2026, from https://smartdefine.org/machiavellian/thesaurus/synonyms
ChicagoSmart Define. 2016. "machiavellian thesaurus" https://smartdefine.org/machiavellian/thesaurus/synonyms (accessed October 1, 2026).
HarvardSmart Define 2016, machiavellian thesaurus, Smart Define, viewed 1 October, 2026, <https://smartdefine.org/machiavellian/thesaurus/synonyms>.
MLASmart Define. "machiavellian thesaurus" 24 March 2016. Web. 1 October 2026. <https://smartdefine.org/machiavellian/thesaurus/synonyms>