There have been countless players better and more talented than Dr. Randy Gregg – certainly many more than the 11 names above him on this Top 100 list – who’ve played for the Edmonton Oilers since 1979. That said, I can’t think of anybody whose path to the NHL and five Stanley Cup parades with the Oilers is as unlikely or as fascinating.
Gregg played 453 regular season games with the Oilers and 130 more in the playoffs on the way to those five Cup celebrations. No small feat for somebody who considered hockey little more than a pastime he’d eventually have to give up when he was accepted into medical school at the University of Alberta. Hardly. Before he was done, Gregg would win two CIAU national titles with the Golden Bears, play for Canada’s Olympic team twice and hoist those five Cups with the Oilers. Oh, and he became a doctor.
Randy Gregg
Defence — shoots L
Born Feb 19, 1956 — Edmonton, ALTA
Height 6.04 — Weight 210 [193 cm/95 kg]

BY THE NUMBERS

Season
Age
Tm
GP
G
A
PTS
+/-
PIM
S
S%
1982-83
26
80
6
22
28
15
54
94
6.4
1983-84
27
80
13
27
40
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40
56
91
14.3
1984-85
28
57
3
20
23
27
32
58
5.2
1985-86
29
64
2
26
28
30
47
55
3.6
1986-87
30
52
8
16
24
36
42
59
13.6
1987-88
31
15
1
2
3
4
8
20
5.0
1988-89
32
57
3
15
18
-9
28
42
7.1
1989-90
33
48
4
20
24
24
42
41
9.8
1991-92
35
21
1
4
5
-3
24
19
5.3
8 yrs
EDM
453
40
148
188
167
309
460
8.7
1 yr
VAN
21
1
4
5
-3
24
19
5.3
Career
474
41
152
193
164
333
479
8.6

PLAYOFFS

Season
Age
Tm
GP
G
A
PTS
+/-
PIM
S
S%
1981-82
25
4
0
0
0
-2
0
5
0.0
1982-83
26
16
2
4
6
14
13
16
12.5
1983-84
27
19
3
7
10
16
21
32
9.4
1984-85
28
17
0
6
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6
19
12
17
0.0
1985-86
29
10
1
0
1
3
12
6
16.7
1986-87
30
18
3
6
9
8
17
29
10.3
1987-88
31
19
1
8
9
17
24
22
4.5
1988-89
32
7
1
0
1
4
4
8
12.5
1989-90
33
20
2
6
8
1
16
17
11.8
1991-92
35
7
0
1
1
3
8
3
0.0
Career
137
13
38
51
83
127
155
8.4

NOTABLE

That Gregg became a reliable and somewhat unheralded member of the Oilers’ blueline at all is remarkable, given the road he took to get to the NHL. His studies, he’d promised himself and his family, would come first. That didn’t stop Gregg from trying out for the Golden Bears. Four years and two CIAU titles later, Gregg joined the Canadian national program and played in the 1980 Olympics. Later, he’d play in Japan. All this before he even accepted a contract offer from Oiler GM Glen Sather.
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“I knew it would be impossible to do medicine and hockey, too, but I also knew that I’d be cut from the team long before it made any difference or before my brother found out,” said Gregg, who couldn’t have been more wrong about not even being good enough to make the Bears. “In a nutshell, two or three practices became ten, then twenty, then we had exhibition games, and, well, four years of university hockey later . . .”
Gregg had three teams bidding for his services, including the Oilers, Calgary Flames and New York Rangers, when he decided to turn pro. He picked his hometown team, leaving a medical internship in town and getting into four games with the Oilers in the 1982 playoffs – he was partnered with Paul Coffey — without having played a regular season game. Gregg became a full-time Oiler in 1982-83. The following season, 1983-84, Gregg enjoyed the best NHL season of his career with 13-27-40 and the Oilers went on to win their first Stanley Cup. Gregg had a career-high 10 points in those playoffs.
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THE STORY

Unlike the stars dotting Edmonton’s line-up, Gregg was never a player who pulled you out of your seat. He didn’t jump into the attack like Coffey did. As big as Gregg was, he wasn’t a banger who punished opposing forwards. He didn’t fight. What Gregg did effectively – most often paired with Don Jackson – was get in the way, concentrate on his own end of the rink, move the puck and make the right play. Gregg was decidedly un-spectacular but unquestionably effective playing behind the big guns up front.
There were some bumps in the road during Gregg’s tenure with the Oilers to be sure. There would be contract holdouts. With the option of a medical career, Gregg retired, however briefly, more than once. He played with Canada in the 1988 Olympics down the road in Calgary. Truth is, Gregg didn’t much like the way the Oilers were being run as owner Peter Pocklington’ financial house of cards began to collapse and players were sold off. Gregg hung on through the 1990 playoffs, becoming just one of seven players to have his name on all five of Edmonton’s Cups.
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Gregg finished his career with the Vancouver Canucks, playing just 21 regular season games and seven more in the playoffs in 1991-92. His last NHL game was May 12, 1992 and it was against the Oilers right here in Edmonton in the second round. The Canucks lost in six games. It just didn’t look right seeing Gregg in Vancouver colors that spring or watching him shake hands with the few remaining former teammates he’d toiled so long and so well with when Game 6 was done. All told, a wonderful and unlikely career as a five-time Stanley Cup champion.
This series will look at the top 100 Edmonton Oilers from the NHL era 1979-80 to 2014-15, starting with 100 and working up.

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