[3][4] Arnold joined WEEI radio at its inception in 1991, at as AM station broadcasting at 590 kHz, then as Sportsradio 850, then moving to WEEI-FM with other locally produced programs.
On February 11, 2008, Entercom put Arnold on the four-person Boston Red Sox radio broadcast team, working with Joe Castiglione when Dave O'Brien was on ESPN.
[5] In February 2011, WEEI shifted Arnold to weekend duty while Holley became co-host of the Big Show during afternoon drive time.
In the 2011–12 season, Arnold returned to NESN as the in-studio host for Bruins broadcasts, anchoring pregame, intermission and postgame coverage.
Daily and weekly guests of The Dale & Holley with Keefe Show included Terry Francona, Mike Milbury, Bill Belichick, Michael Irvin, Peter King, Patrick Chung, Matthew Slater, Dont'a Hightower, Vince Wilfork, Chris Mannix, Jackie MacMullan, Trent Dilfer, and Pierre McGuire.
On August 13, 2018, WEEI shook up their lineup, moving The Dale & Keefe Show to the midday slot, and moving the midday show, Ordway, Merloni, and Fauria, featuring hosts Glenn Ordway, Lou Merloni, and Christian Fauria, to the afternoon drive time slot.
[11][12] In November 2024, NESN announced that Arnold would return, on an interim basis, to handle studio duties for Boston Bruins pregame and postgame shows, to help balance the workload of other on-air staff members.