The name CrankMail was coined by Brett Braden, an original member of the Lake Erie Wheelers, while the magazine itself was founded by Harold Albus. The first issue likely came out some time in 1974, but the exact date has not yet been definitively ascertained.

In 1978, a group consisting of Eric Schultz, Diane Romano (then-owner of LBS Bicycles, now Diane Lees, owner of Hubub Custom Bicycles), Al Marcosson (then-owner of Goodstuff, now owner of Pyro Apparel), and David Fortier (founder/director of Tour Along the South Shore of Lake Erie, or TASSLE) approached Albus with some ideas for the magazine. His response was "I wanted some help, not a takeover!," but he nonetheless turned things over to these four.

Fortier assumed the role of general editor, honored CrankMail's founder by posting a caricature of Harold on the masthead, and maintained an "all copy welcome" policy, which led to some interesting submissions, such as the multi-part classic, "Scientific Gear Selection," and the popular cartoon, "A day in the life of . . . Superbikie!!!"

Guilford changed printers upon assuming editorship, reduced the size to an 8.5" x 5.5" "mini-magazine" format, switched to proportionally-spaced fonts, and generally upgraded CrankMail's appearance and editorial standards, as reflected his journalism background. As a result, CrankMail looked less like a newsletter, and more like the "micropress publication" that it was. What would be most interesting about this period are the changes in technology, such as from paste-pots and scissors to electronic copy editing.

Sometime in the late 1990s, Guilford turned over the collating and stapling to the printer. Previous to that, it had been done by a group of volunteers, most of whom were members of the Lake Erie Wheelers, including John, Jane, and Dick Wasko; Tom Nezovich; Carol Petsche; Tom Smeal; and John Whitaker.

In late 2003, Guilford turned over the editing reigns to "two of the best from local cycling leadership" -- Marty Cooperman as copy editor, and Tom Meara for editing and layout. Guilford's farewell can be found here: CrankMail Archives Nov/Dec. 03'.

In late 2006, Meara decided to step down from CrankMail to pursue other interests, including but not limited to doing the Lewis and Clark Ride, and the new triumvirate of editors (Doug Morrison, Cory Smith and Marc Smith) produced their first issue in March 2007, which showcased some of the changes in their master plan: a "full bleed" format and 80# text gloss "magazine" paper.

All three of the new editors are cyclists, currently residing in Medina.