(MONEY Magazine) – Sure, mob boss Tony Soprano enjoys a six-figure income from his waste-management firm and the Bada Bing strip club (plus various less public enterprises). But his financial planning is so bad, it's downright criminal.

• SAVINGS Tony socks cash away in non-interest-bearing duck-feed bags under his utility shed. To avoid a hit from inflation, Chris Cordaro of RegentAtlantic Capital in New Jersey suggests a municipal bond portfolio with staggered maturities of up to five years for flexibility. Tony would earn 3% to 4% triple tax-free, and Tony likes tax-free.

• TAXES Soprano gets whacked by the alternative minimum tax, which won't let him deduct Jersey's state income tax (tiered up to 8.97%) or property taxes. By contributing more earnings to retirement plans (profit sharing from the Bing and a pension from Barone Bros. Sanitation), Cordaro says, Tony could reduce taxable income and maybe avoid the AMT.

• LIFE INSURANCE "He's certainly at risk for premature death," says Paul LaViola of Financial Planning Solutions in Media, Pa., who recommends that Soprano fund an irrevocable life insurance trust with annual gifts. The trust would technically own and pay for a multimillion-dollar policy, so it would pass to Tony's kids, A.J. and Meadow, free of estate taxes.

• HEALTH CARE A flexible spending account could cut taxable income by $5,000 and help pay for prescriptions or, oh, perhaps pricey top-secret psychiatric sessions.