A: I just couldn’t believe it when I heard Michael is in jail. He’s the brightest in our high school class.

B: What a shame! The judge sent him up the river for five years due to blackmailing a famous singer.

Note: This idiom means “to sentence one to prison” or “to cause one to go to prison.” This phrase originates from the fact that convicts from New York City would be sent up the Hudson River to Ossining State Prison (“Sing Sing”). The maximum-security prison is located in the village of Sing Sing on the east bank of the Hudson River, some 48 kilometers north of NYC.