Dash, who co-founded the star's Roc-A-Fella Records and Rocawear clothing line, has been drowning in debt since the old pals parted ways in 2004 and he was recently hit with a new bill from the Internal Revenue Service to the tune of $2.8 million (£1.8 million) after allegedly failing to pay federal taxes on earnings from 2005 and 2011.
He has also been working to pay off a separate tax bill to New York state officials, which stands at over $2 million (£1.29 million), and has been facing legal action over a 2006 loan he reportedly reneged on, in addition to fighting eviction from his home in Carmel after struggling to pay his rent.
However, Jay Z is adamant Dash will find a solution to his money troubles.
During an interview on New York's Power 105.1 station on Wednesday (10Jul13), he said, "Dame's a hustler; Dame will figure it out. Dame's a very smart guy so he'll figure it out."
The Empire State of Mind hitmaker insists he bears no ill will towards Dash and will always be rooting for him because, despite the breakdown of their friendship, they will always share a special bond and a place in hip-hop history.
He explained, "What people gotta (sic) understand is nothing's gonna change the way I feel about Dame; no time or space, no separation or anything. I got love for Damon Dash the same way as I did before (we split professionally).
"I don't know if we can be around each other in the same way because times have changed. He might be a completely different person; I know I'm a completely different person. But nothing can erase that era and those times and those memories and those fights that we had to get Roc-A-Fella where it was. It just is what it is. Nothing's gonna change that...
"The relationship remains and those memories remain. We did something great; we built something that's gonna be here forever, that's gonna be talked about forever so there will always be love there."
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