Usher Raymond was spotted out and about on the streets of NYC recently with his current boo, Grace Miguel.

The multi-talented singer apparently has a habit of falling for older women and letting them affect his business decisions.

When he chose to marry Tameka Foster Glover Raymond, she put her foot down and fired his entire staff, including his mom/manager Jonetta Patton, who he subsequently rehired after realizing his mistake.

Well now it looks like history is repeating itself for poor Ursh.

Word on the curb is that his current lady love, 43-year-old former Def Jam executive, Grace Miguel has filled Meka’s shoes quite nicely. Grace, who reportedly acts as Usher’s co-manager and stylist, has urged the R&B superstar to cut his entire team and replace them with her people of her choosing!

Details below:According to PageSix:

Usher’s longtime agent, Mark Cheatham of CAA, is the first victim of his much older girlfriend. Usher, 32, started his career with Cheatham and introduced him to teen sensation Justin Bieber, whom he currently represents.

Cheatham was tight-lipped when we contacted him. “I don’t know anything about it. I’ve been with Usher for a long time,” he told us. “I’ve been on great terms with Usher. Talk to my publicist.”

A CAA publicist never got back to us, but Usher is no longer listed on their client list.

A source close to Cheatham tells us, “Mark is really upset. He’s been with him from the beginning. He thinks Usher will come back, He’s just waiting.”

Usher has a history of mixing business with pleasure. In 2007, he married his stylist, Tameka Foster, with whom he has two children. He filed for a divorce in 2009. When Foster was at odds with his mother and manager Jonetta Patton, Usher showed his mom the door.

Usher explained to Vibe: “[I paid her] the ultimate compliment — to retire her to be a full-time grandmother.”

Now it’s Miguel who’s apparently got his ear. A source told us, “Usher will do whatever she wants him do right now.”

Is Grace Miguel ‘Tameka 2.0’?

What is it about Usher and these cougars? He must have some serious mommy issues…