Landlord issues

I’ll probably have to take some sort of legal action to get my security deposit back from one of my old roommates (who paid the original $1600, then other roommates paid him to make it even).

• Option 1. My landlord pays the money directly to me since I have check scans proving that I paid for the deposit. If Kevin, the other roommate, decides to sue the case gets thrown out in 10 minutes with any slightly more than half-assed lawyer. This plan is supported by two lawyers, one who specializes in rental property disputes, and a real estate developer/manager who owns over $50 million in properties across the midwest.
• Option 2. My landlord gives the entire deposit back to Kevin. I would have to sue Kevin for the money, which would be a much longer and drawn-out deal for everyone, including the landlord. People who back this plan: my landlord. 

GGGAAAAHHH.