AITAH - Best Friend Loan

5yrs ago loaned him 5k with a notarized legal agmt stating no interest, repayment within 7 days of law suit settlement. (Hurt on the job - he was drowning financially out of work) loan was repaid 72hrs after settlement 3yrs later. Two yrs after, he was living out of his means and there was no talking to him. He called, he overspent and asked to borrow $400 for car pymt. Said check due in 10days repayment right after. Have never seen a dime. Lesson learned. Today, 2 yrs from that loan, he’s completely blown thru 6 figure legal settlement. Yesterday he asked for $270 to cover concert tix for son he paid for 2 weeks prior, but now short for living expenses. I had some words said id think about it but have decided no more loans moving forward. He’s furious. I loved our friendship for decades but his finances are getting worse fast and he’s unhealthy and always looking for the easy way. AITAH for not loaning the cash? Can our friendship survive this? It’s just getting a point I am weary to even take his phone calls anymore.