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Watching many of the Raw episodes since starting this project, one thing has struck me most was the genuine friendship that seemed to exist at the time between McMahon and Savage who were regularly a commentary pairing on Raw in 1993 and 1994. This wasn't a pairing that would win any awards for great wrestling announcing, but the two seemed to have great chemistry and you could sense genuine candid moments during squash matches on Raw when Vince would rib Savage about an upcoming link for the USA Network he was about to plug. Savage's departure to WCW is probably the most reliable account of why (up until recently, it seems) Savage's position in the Hall of Fame has been vacant. On a 1993 edition of Raw Vince would call Savage "unquestionably a future WWF Hall of Famer".
Savage's last major feud in the WWF was with Crush, a feud built on the defection of Crush to the dark side with Mr Fuji and Jim Cornette. Savage would play his role very well in a feud that went from late 1993 to Wrestlemania X. The culmination, a falls count anywhere match, was a bit of a disappointment and was largely forgotten in amongst two great matches on the card. Savage would return to his announcing role, but would still have time to play a minor role in the build of Bob Backlund before he would win the WWF Title from Bret Hart.
It's said that Savage's departure surrounded his desire to still be used as an active performer. There were little signs in late 1994 that Savage was been used as anything more than an announcer, and with WCW looking to push the boat out into 1995, and their inability to create any viable contenders to Hulk Hogan off their own back now Flair was "retired", bringing in Savage would be a logical move.
Losing Savage wasn't a big blow in itself to the WWF. He was a familiar face on Raw programming, but he wasn't a great announcer and nor was he likely to play a part in ring going forward. But to lose him to WCW was a big blow, a signal in the slow moving powershift over to WCW that would continue for the next few years. It would be one thing if the WWF were creating newer stars for the New Generation (as they would try and fail at with Diesel for the next 12 months), but to lose an asset that could've righted the ship was a big blow. For Vince, personally, it may also have been a big loss, their friendship seemed strong, and Savage was one of the last remaining big stars in the company from the hot run in the 1980's.