What is the greatest possible sum of the digits in the base-seven representation of a positive integer less than $2019$?
$\textbf{(A) } 11 \qquad\textbf{(B) } 14 \qquad\textbf{(C) } 22 \qquad\textbf{(D) } 23 \qquad\textbf{(E) } 27$
Observe that $2019_{10} = 5613_7$. To maximize the sum of the digits, we want as many $6$s as possible (since $6$ is the highest value in base $7$), and this will occur with either of the numbers $4666_7$ or $5566_7$. Thus, the answer is $4+6+6+6 = 5+5+6+6 = \boxed{\textbf{(C) }22}$.
~IronicNinja went through this test 100 times