(CNN) -- Chris Brown's nightmare cross-country trip to face trial in Washington ended Monday five days after it began in Los Angeles.
The singer's "Con Air" flight landed in the D.C. area, and he was escorted by U.S. marshals to a local jail where he will be locked up until his assault trial later this month, according to a Marshals Service spokesman.
He had been chained at his ankles, waist and arms much of the time since marshals took him into custody from the Los Angeles County sheriff last Wednesday.
Brown's lawyer failed to convince a judge at a hearing Monday that his assault charge in Washington should be dropped because of prosecutors' misconduct. Judge Patricia Wynn rejected the argument by Mark Geragos that the U.S. attorneys abused the grand jury process in preparation for Brown's trial.
The singer and his bodyguard, Christopher Hollosy, are charged with hitting a man on a sidewalk just blocks from the White House in October.
But Wynn did grant Geragos' request to hold separate trials for Brown and Hollosy. The bodyguard's case will be tried first on April 17, with Brown's trial to follow on April 21, Geragos said. The would permit Hollosy to testify for Brown, he said.
Although the charge is a misdemeanor and is unlikely to carry jail time for Brown if he is convicted, the arrest has put him behind bars because of his probation for an attack on ex-girlfriend Rihanna five years ago.
Brown, 24, did not attend a hearing Monday in a Washington courtroom because he was still on his way to the nation's capital through the Justice Department's prison transport system.
Even if Brown is acquitted, he could still have to return to Los Angeles the same way he got there -- in custody. Geragos could be expected to ask the Los Angeles judge to let Brown return to California on his own in that case. It's the difference between flying five hours in first class or spending five days in chains with federal prisoners as seat mates and marshals as flight attendants.
He was ordered to jail after he was booted from a court-ordered rehab program last month, complicating his travel arrangements for the assault trial. A Los Angeles judge refused to release him to travel on his own because his California probation had been revoked as a result of his arrest in Washington.
U.S. marshals picked Brown up in Los Angeles on Wednesday for the start of the trip to Washington. Con Air -- the nickname for the federal government's Justice Prisoner and Alien Transportation System -- involves heavily guarded passenger planes that hopscotch the country, picking up and dropping off prisoners.
Brown's legal troubles began five years ago when he beat Rihanna as the two were in a rented Lamborghini on a Hollywood street. He pleaded guilty to felony assault in June 2009, which resulted in a sentence of five years of probation and 1,400 hours of community "labor-oriented service."
The judge has revoked Brown's probation twice in the past year, most recently because of his Washington arrest.
Brown voluntarily entered a rehab program a day after being released from a Washington jail in October, but he was kicked out a few days later for "throwing a rock through his mother's car window" after a family session at the center, a probation report said. Brown was upset because his mother said she wanted him to stay in treatment, the report said.
Brown proceeded "to walk outside and pick up a rock and threw it through his mother's car window and it shattered," according to a letter from the rehab center included in the probation report.
His probation was revoked in November, but the judge allowed him to stay out of jail by entering a 90-day anger management and drug rehab program. Although he completed that program last month, the judge ordered him to remain a resident at the Malibu, California, treatment facility until another hearing April 23.
Brown's probation officer reported at a February hearing that the singer "continues to make great improvement" in dealing with anger, stress and drugs, but the judge decided he could not go free until after his trial for an assault charge in Washington on April 17. If he is convicted in that case, the judge would decide at an April 23 hearing whether Brown should complete his probation in jail.
He was sent to jail March 14 after he was kicked out of the second rehab program for rules violations.
The judge said he was concerned about a "provocative" statement that counselors said Brown wrote on a card at the Malibu rehab center. "I am good at using guns and knives," according to a document read in court.
The rehab program told Brown to leave because of that statement and two other rules violations, the document said. Brown refused a drug test -- which his lawyer denied -- and he touched elbows with a female patient, according to the document.
Brown had been working on a highway cleanup labor crew in Los Angeles three days a week to fulfill the 750 hours of service remaining in his probation requirements, his probation report said. At that rate, Brown could complete the labor in mid-October and possibly be free from probation requirements by the end of the year. With his community labor work now on hold, his probation is expected to extend into 2015.
CNN's Carolyn Sung contributed to this report.