彼がしくじったら気の毒だ。

彼がしくじったら気の毒だ。

It'll be a pity if he fails.

彼(かれ)がしくじったら気(き)の毒(どく)だ。

Kare ga shikujittara kinodoku da.

彼 (かれ)

he; him; his; boyfriend

が (が)

indicates sentence subject (occasionally object); indicates possessive (esp. in literary expressions); but; however; still; and

しくじる (しくじる)

to fail; to fall through; to blunder

気の毒 (きのどく)

pitiful; unfortunate; (a) pity

だ (だ)

be; is; indicates past or completed action; indicates light imperative

Readings: ヒ、かれ、かの、か.の

Meanings: he, that, the

Readings: キ、ケ、いき

Meanings: spirit, mind, air, atmosphere, mood

Reading: ドク

Meanings: poison, virus, venom, germ, harm, injury, spite