Chris came into contact with Savatage and they asked Chris to join them just as the “Gutter Ballet” album was finished. He was part of the recording of 1995's “Dead Winter Dead” and 1998's “The Wake of Magellan”. Chris recorded with Joe Lynn Turner, TM Stevens, as well as produced and recorded for Metalium.
Chris was featured on Tribute CDs for Guns N' Roses, Accept and Iron Maiden.
Savatage was stalled a bit in the recording of a follow up to “The Wake of Magellan”, due to the tremendous success of the then "side project", Trans-Siberian Orchestra. Caffery considers himself the "ring leader" of TSO East when they tour, and he enjoys performing live with the ensemble.
In 1999, Caffery also was a member of the German band Metalium. He is featured on their album “Millennium Metal: Chapter One”, but left after the album and the following tours.
Al Pitrelli left Savatage in 2000 when he accepted an invitation to replace Marty Friedman in Megadeth. Chris was left as the only guitarist in Savatage and Jon Oliva took up lead vocal duties for the first time in ten years.
Chris played the lead parts in Savatage 2001's “Poets and Madmen”. Since the release of Savatage's most recent CD, Chris has appeared on records of Savatage alumni, including Zak Stevens's “Circle II Circle” and on Jon Oliva's “Pain” records. Chris himself released solo EPs and albums in 2004 and 2005, with a follow-up full-length album, “Pins and Needles” released in 2007.
Chris has also worked on TSO's new album “Night Castle”, released on October 27, 2009. In 2011,
Chris released his first commercial hot sauce called "Tears of the Sun".
It was released through a small hot sauce company called High River Sauces that belongs to his partner Steve Seabury and his wife. The sauce won major awards including "The Hot Pepper Award" for best overall Hot Sauce in 2011.
A second sauce called "Grapes of Wrath" was released in 2012. The sauces are gaining a lot of attention world-wide as the venture continues to grow and were included in a featured articles in the "New York Post" highlighting Chris's sauce and at the first ever New York City Hot Sauce Expo!
Musically Chris appeared on several releases as a guest musician. He also toured as the guitarist for the legendary German Metal vocalist Doro as well as a solo tour supporting Heaven and Hell with Tim "Ripper" Owens' band in Europe. He co-wrote and played the guitars on the song "The Shadows Are Alive" on Tim's first solo release entitled "Play my Game". TSO continued its yearly winter tours and also performed three tours for its Beethoven's “Last Night” CD.
The second tour saw TSO cross overseas to Europe for the very first time. In addition to several more guest appearances and collaborations Chris also appears regularly with 18 time Grammy award winner Jimmy Sturr. He also starred as a guest on two episodes of his national TV show. Other current ventures include personal and online guitar instruction, additional culinary adventures, book writing, painting/sketching, photography, musical production and public speaking.