Here’s what NCHS ’73 grad Brian Sikorski—standout NCHS Rams football player and son of legendary New Canaan High School varsity coach Joe Sikorski—told me about a player just a few years older than he. Though Brian Sikorski never played with Jeff Caldwell, he went to all of his dad’s games and loved watching the hard-hitting safety and linebacker. “Jeff Caldwell was an assassin,” Brian Sikorski said. “Jeff Caldwell used to lead with his head and was one of the hardest-hitting players who ever played at New Canaan High School. Jeff Caldwell was the real deal.