Is Ice Cube facing a “damned if you do, damned if you don’t” time in his life? We are sure, as a Black man, he has had many, but maybe not particularly when it comes to politics, which many critics say he should have steered far away from –especially during this critical election period.

Cube has been taking a beating by many African Americans who feel that he is supporting President Donald Trump, but the legendary rapper says, that is NOT SO, and in fact, he is only trying to support and advance his people.

The legendary rapper who changed the face of hip hop as we know it, being one of the most powerful forces behind the iconic rap group “NWA,” shook up fans after it was recently revealed he spoke to people in the Trump organization about implementing his “Contract with Black America.”

All hell broke loose across “Black Twitter, then sweeping to mainstream media, after Cube tweeted that the Trump campaign made adjustments to “their plan” for Black America after talking to him.

The “F*** tha police” rapper was referencing his own “Contract With Black America,” calls for “a blueprint to achieve racial and economic justice” through polices that promote wealth creation, home ownership, small businesses criminal justice reform, and voting rights. Small parts of the “Contract” are reflected in what the Trump administration has dubbed its “Platinum Plan” with election time appeals to Black voters.

Now to be fair, Cube reached out the both Democrats and Republicans and while he said the Democrats put off meeting with him for a later time, Republicans were willing to talk.

“I’m not playing no more of these political games, we’re not part of a team … so I’m going to whoever’s in power and I’m going to speak to them about our problems, specifically,” Cube said in an interview with CNN’s Chris Cuomo. “I’m not going in there talking about minorities, I’m not going in there talking about people of color or diversity or none of that stuff. I’m going there for Black Americans, the ones who are descendants of slaves.”

Though he denounced Trump in 2016, Cube’s “willingness to work with” the administration is confusing to some, who feel he should not be affiliated in any shape, form, or fashion with a man whom many feel is leading the war against Blacks and other people of color, promoting racism and allowing police brutality.

Adding fuel to the power, rapper 50 Cent sent more shockwaves after announcing plans to vote for Trump after previously criticizing him. 50’s endorsement was reportedly in response to Joe Biden’s tax plan.  50 Cent posted on social media: “I don’t care if Trump doesn’t like black people.”

It has been reported that more Black men are coming out in support of Trump, who has stronger polling numbers on issues dealing with the economy, while Black women support the Democratic Party.

Black women are blazing more a trail these days in politics, with the obvious excitement behind Sen. Kamala Harris’ historic vice presidential run, in addition to others like Rep. Ayanna Pressley in Massachusetts, Congressional candidate Cori Bush in Missouri and former gubernatorial candidate

Stacey Abrams in Georgia. Black women are on the forefront of helping to transform the political climate of America.

Noted in an op-ed by Peniel E. Joseph, history shows us that Black leaders have tried, and failed, to bridge the gap between racist organizations and Black America. Malcolm X and the Nation of Islam privately met with representatives of the Klan to speak on racial integration, but their well-intended efforts were morally compromised and ended with no positive results.

And in the aftermath of Martin Luther King Jr.’s assassination, Black Power activist and Black Studies scholar Maulana Karenga was pilloried for attending a private meeting in the late 1960s with then-California Gov. Ronald Reagan.

Congress of Racial Equality leader Floyd McKissick went from marching alongside Stokely Carmichael and King in Mississippi to publicly supporting Richard Nixon, whose broken promise to support an all-Black “Soul City” in North Carolina is a tragic exemplar of what negotiating with groups hostile to the idea of Black citizenship and dignity actually achieves.

Ice Cube’s “Contract With Black America” contains some important policy recommendations that, if achieved, would help millions of African Americans enjoy better access to wealth, economic justice, voting rights, and less punishment at the hands of the police, but Joseph feels his “blueprint” falls short of the radical policy recommendations championed the Black Lives Matter Movement, in addition to other Black activists, organizers and everyday people fighting for equal rights.

Even though it may have been a noble effort, critics say Cube was not politically educated, did not reach out to other leading Black organizations for assistance and should have just stuck to entertainment.

But at the end of the day, he did TRY to help and a conversation HAS BEGAN….. so is it a “damned if you do, damned if you don’t” kind of teachable moment?