Can March Madness Pools Land You in Jail?

As March Madness gets going in full today and tomorrow, the brackets will be finished and dollars (allegedly) collected for the office pools, but what about all those online pools, even the ones managed by the guy down the cubicle.

Can the manager, with a simple intonation of receiving a few bucks, be converged upon by the Feds, or are there ways around running the pool and staying free of the laws of internet gaming and gambling for the estimated 58 million brackets that are filled out this week?

Or, as in the case of a fifth-grader in Omaha, can it land you in the principal's office?

Some of the answers were presented in Ira Boudway's piece in this week's Bloomberg Businessweek.

Boudway looked back at as far as 1996, when Chris Hehman built one of the first online bracket managers for the NCAA men’s college basketball tournament, and how he wrote a program that scored the 63 picks on every bracket automatically. 

Since his company, Nortel, owned the original software, he rewrote it from scratch and put it online.

In that first year, a few dozen people paid $9.95 to use the service to run a pool.

That site graduated into Pickhoops and was the forerunner of the 5.9 million that use ESPN or the 4.5 million at CBSSports. 

For those who do collect fees, are they breaking a law or two, or following the guidelines?  And can companies like PayPal, who provide back-end services for any kind of payment, be responsible as the Federal Government cracks down on internet-related gambling of all kinds?

It poses all kinds of questions for those around the office, and for those holding the envelope.