Mike Flanagan is, of course, one half of the two-headed not-GM situation the Orioles have right now. He also had quite an interesting pro career, peaking early and falling apart some due to injury, but hanging on until he was 40 years old anyway.
Flanagan was drafted as a 21-year old in 1973, taken by the Orioles in the seventh round. He was an offspeed guy, relying on the curve and change, similar to Bruce Chen now. The immediate instinct was to say Flanagan was a lot better than Chen, but that could be premature; Flanagan wasn't much younger than Chen when he broke out, just a couple years.
He first came up in '75, at 23, pitching in two games with some lucky results. In '76, he appeared in 20, half of them starts, and put up a 4.13 ERA, which wasn't near as good in 1976 as it is now; his adjusted ERA+ that season was just 79, which is Ponson-like nowadays.
Flanagan became a full-time member of the rotation in '77, pitching 36 games and starting 33 of them, with 15 complete games. He got his ERA (3.64) a little better than league average that season (3.79), and went 15-10. In '78, he was 19-15 over 281 innings. He was again mediocre, really, supported by a good team. He put up an 87 in adjusted ERA+ that year, this pitching most of the time at pitcher-friendly Memorial Stadium.
1979 was Flanagan's breakthrough season. He went 23-9 and won the Cy Young and Sporting News Pitcher of the Year awards. He wasn't really the best pitcher in the league, but that's voting for you. Ron Guidry was, for the second year in a row, the best starter in the league. However, 1979 was Flanagan's best year, and by a lot. He finished fourth in ERA (3.08), fourth in W-L percentage, third in WHIP (1.18), third in strikeouts (190), fifth in adjusted ERA+ (130) and sixth in H/9 (8.30).
After that, Flanagan returned to mediocrity in 1980 and 1981, but had a fair season in '82 and his second-best year in '83, when he made just 20 starts due to injury. Flanagan was healthy and good again in '84. After that, he was hurt the next three seasons, and traded to Toronto for the '87 stretch run. The Orioles acquired Oswaldo Peraza and Jose Mesa (then a "21"-year old starter) in the deal. Flanagan tested free agency, but stayed with Toronto for the next three years. He was a bit below average for the first two, then hurt again in 1990.
For the 1991 season, he signed again with the Orioles, working as a reliever exclusively for the first time in his major league career. He was fantastic in relief in '91, putting up a 2.38 ERA over 98 innings, but imploded in '92. He appeared in 42 games, pitching more as a LOOGY, but just couldn't get hitters out. He retired after posting an 8.05 ERA, playing his final game on September 27, 1992; 17 years and 22 days after he made his big league debut.
Now the interesting thing about Flanagan is that when you stack it all up, he was maybe the most average pitcher to ever live. He had a career 3.90 ERA; the league averaged 3.90 over his career. He struck out 4.84 per nine, and walked 2.89, neither really good numbers. Flanagan really didn't do anything exceptionally well. He had a couple of real good seasons, but even those weren't great by any stretch.
He has always been regarded as very intelligent, so it's not surprise that what was - more or less - a career Oriole would wind up in a position of power with the team. He hasn't had long enough to screw anything up too royally, nor has he had the amount of time needed to consider him really good.
Where does Flanagan rank all-time among Oriole starters?
Well, for modern times, he's behind Palmer and Mussina for sure, but he's not too far behind McNally or Cuellar, both of whom had more wins because they played on better teams, but not so much because they were terribly better pitchers. Basically, if Flanagan had been born ten years earlier, he would've had 180-190 wins, like Cuellar and McNally did. Flanagan was better than Scott McGregor. Orioles-wise, he is better than Dennis Martinez, who had three true stinker seasons in a row before he was sent off to Montreal, where he found himself and became a damn good pitcher. Going back a bit more, he was not in the same class as Milt Pappas.
He ranks fifth all-time in Orioles history in wins (141); third in games pitched (450); fourth in strikeouts (1297); third in games started (328); tenth in complete games (98); tenth in shutouts (17); third in losses (116, behind Palmer and Jack Powell).
But the one that sticks out to me is that he threw more innings in an Orioles uniform than anyone besides Jim Palmer and Dave McNally. For all his faults as a pitcher (and he had plenty), Flanagan was, and is, a Baltimore Oriole.