Bob Whitsitt was active at the Midseason Trade Deadline, except in his last Blazer years when the Oregonian was wearing him down. In 16 Midseason Deadlines (plus a 50-game season), he had 9* major trades, which qualifies as a bunch. Olshey won't be a full-time GM until he trades/signs all year round.
SONICS
1987* signed Eddie Johnson
1988* Sedale Threatt for Sam Vincent
1989 signed Greg Ballard and Mike Champion to 10-days
1990* Steve Johnson and a #2 for Brad Sellers
1990 signed Quintin Daily and Jim Farmer to 10-days
1991* Ricky Pierce for Dale Ellis
1991* Benoit Benjamin for Olden Polynice and #1s (LeRon Ellis, Brooks Thompson)
1992 signed Tony Brown to a 10-day
1993* Sam Perkins for Benoit Benjamin, rights to Doug Christie
1994 signed Alphonso Ford to 10-day
BLAZERS
1995* Thorpe and a #1 (Childress) for Drexler and Murray
1996 signed Rumeal Robinson to a 10-day
1997* Augmon for McKie and Childress
1997 signed Nembhard 10-day, waived Ennis Whatley
1998* Damon Stoudamire, Walt Williams, Carlos Rogers for Kenny Anderson, Alvin Williams, Gary Trent, #1s (Bryce Drew, Mirsad Turkcan), #2 (Tyson Wheeler), cash
1998 signed Gary Grant 10-day, waived Dontonio Wingfield and Vincent Askew
1999 50-game season
2000 none
2001 waived Gary Grant
2002 none
2003 none