Raised in
Mahwah, New Jersey, Caffery began playing guitar at age 11, but some of his earliest memories include performing
the Beatles song
Help! for a
show and tell in kindergarten. Caffery's favorite bands growing up included
the Beatles,
Kiss,
Black Sabbath,
Judas Priest and
Rush among others. He has cited guitarists such as
Ted Nugent,
Rik Emmett,
Ace Frehley,
Randy Rhoads,
Michael Schenker as influences throughout the years as well. After only 13 months, Caffery grew bored with guitar lessons and decided to teach himself. He was part of a band called
"Blitzkrieg" in middle school and played a few shows, the first of which was at a bar in
Ridgewood, New Jersey when Caffery was only 13. At the age of 14, he and his brother formed a band called
"Anti". Caffery graduated from Goshen Central High School in 1984 and went on to become a professional musician, teaching students during the day and playing shows in the night. Caffery recorded his first demo tape at age 14 and his second at 17, which got him his first national gig. Caffery was in New York City one night, hanging around in a club in the middle of
Times Square, when he met the lead singer of a band called
Heaven named Allan Fryar. They were looking for a guitarist and Caffery asked if he could give Allan a tape. A week later and Fryar called, and it turned out that the band also needed a drummer, so Caffery's brother Phil joined. The band was managed by David Krebs and a certain
Paul O'Neill, who Caffery would maintain close ties for most of his career. Paul O'Neill was later introduced to the Oliva brothers,
Jon and
Criss of Savatage by an
Atlantic Records rep and O'Neill left Heaven to work with
Savatage. Eventually, Paul invited Caffery to New York, where they recorded the CD and introduced Caffery to the band. But, Caffery soon learned that a second guitarist may be needed in Savatage, so he learned all of the Savatage songs he could in time for Savatage's 1987-1988 tour with
Dio and
Megadeth. Savatage hired someone else, which left Caffery very upset and he flew himself down to the audition. Caffery was given the opportunity to perform, played 2 songs before the band stopped and hired him on the spot. The band went on tour, but Caffery was kept on the side of the stage, hidden from the audience. Caffery was only 20 years old and playing arenas and was happy, but miserable. He left Savatage after the arena tour. Caffery bounced between bands for a couple of years until he came into contact with the Oliva brothers once more. They asked Caffery to join them just as the
Gutter Ballet album was finished; despite the fact that he never played on the album, Caffery was credited with guitars and keyboards and is pictured in its booklet "both to prepare the fans for the line-up they'd see on tour and confirm his permanent member status". He agreed to join Savatage, but the road took its toll on the band. With outside pressure to finish their dreams of a band together Caffery regretfully quit Savatage at the end of the tour and formed Witchdoctor, with his brother Phil on drums, Hal Patino of
King Diamond on bass, and future TSO West member Doug Kistner on keyboards. The band played all over America however the brothers were not clicking musically and the band disbanded. Caffery was contacted to perform on Savatage's
Streets tour, but issues meant this did not happen. Caffery soon learned that Jon Oliva had left Savatage. Caffery called Jon, who invited him to Florida, and over "10 bottles of Jack Daniels", Caffery was asked for the fourth time to join Savatage, but Atlantic Records suggested
Alex Skolnick join the band instead. Caffery would later work with Alex on the TSO East touring company. Butcher was signed in Europe and
their debut was recorded in 1994. Jon Oliva left to do the
Handful of Rain tour with Savatage so Butcher never toured. Caffery, this time, enquired about joining Savatage on a more permanent basis with Jon Oliva, as a close friend and student of Criss Oliva he felt he could pay respect to Criss "spiritually" on stage. Jon agreed, and Caffery was joined by
Al Pitrelli, a good friend of his from New York. The two formed a steady partnership for almost 6 years, recording both 1995's
Dead Winter Dead and 1998's
The Wake of Magellan together. During this time, Caffery recorded with
Joe Lynn Turner,
TM Stevens, as well as produced and recorded for
Metalium. Caffery was featured on tribute CDs for
Guns N' Roses,
Accept and
Iron Maiden. The Iron Maiden tribute was recorded with Savatage drummer
Jeff Plate and his "long time and newly re-acquainted best friend", TSO member,
John West. 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. Zak Stevens left shortly after, citing family reasons. Caffery was left as the only guitarist in Savatage and Jon Oliva took up lead vocal duties for the first time in ten years. Caffery played the lead parts with Jack Frost (ironically, who replaced him in Metalium) playing the rhythm parts on a short tour with
Fates Warning and
Judas Priest in support of 2001's
Poets and Madmen. After Megadeth "disbanded" (it later reformed in 2004) in 2002, Al Pitrelli was invited to re-join the band since "he never left the family anyway". as well as several other musical projects. In 2016, Caffery played lead guitar with
thrash metal band
Metal Church, as a touring substitute for regular guitarist, Rick Van Zant, and playing alongside his
Savatage bandmate
Jeff Plate. ==Solo band members==