Brett Tracy: 303 wins
Some other guys: less than 200 wins
Those "other guys" include a few active pitchers with 190+ wins. 35-year-old Ted Davis has 195 wins but has a 4-10 record in St. Louis this year. 41-year-old Tom Hudler sports 196 wins and a 1-5 record in S19. Although Hudler is an uncertain bet for 200 wins, Davis should crank out a few more productive years and could conceivably end in the range of 220 to 230 wins.
Neither has a prayer of reaching 300 wins.
This is a little exercise about whether Rick "Bridesmaid" Christensen has a legitimate shot at 300 wins. First, a little background. Christensen was drafted in the first round of S9 as a 20 year old, junior college pitcher. He was called up in early June of S12 as a 23-year-old. In his six full seasons since then, Christensen has averaged 19.8 wins per season and is on pace to eclipse that this season (13 wins at the all-star break).
We're going to attempt to project Christensen's career. As comps, we're going to use Brett Tracy and Ted Davis. Neither is a perfect comp, of course, but Davis has a similar makeup and could help us to attempt to predict Christensen's decline phase and Tracy, while mostly incomparable, does serve as our only guidepost to 200+ wins, much less 300.
Davis has continued to pitch without any loss of effectiveness through his current age 35 season. Tracy, with lesser makeup, continued to have "top of rotation" performance and ratings through his age 36 season (S14) and was still very effective in his age 37 season. We'll assume that Christensen's higher makeup (18 points higher than Tracy) and the $20M training budget in Cleveland will extend Christensen's effectiveness at least one additional year.
Let's go to the numbers. We'll assume that Christensen finishes this year with 20 wins and then matches his average of 19 wins per season through age 37. We'll assume that despite 82 health he never suffers a catastrophic injury. After age 37 we'll assume a reasonably steep decline phase. We'll also assume that Christensen remains with Cleveland and that Cleveland continues to employ a team of similar quality.
(Guesstimate seasons are listed in blue italic).
Wins At Same Age
It appears as if Christensen does have a legitimate shot at 300 wins if he continues to go injury free. In the case where a minor injury leaves him just a few wins shy of 300 wins at age 40, Cleveland or some other team will likely bring him back at ages 40+ to reach 300 wins. This might give him a 15 to 20 win buffer on reaching the 300 win milestone.
If Christensen wins 20 games this year, he'll be 23 wins behind Tracy's pace, but he is projected to have an extra season of top-notch effectiveness at the tail end of his career. Christensen also benefits from the expectation that he'll finish his career with a top-tier Cleveland team while Tracy was hamstrung by spending parts of S11 on the 74-win Yanks and S13 on the 61-win Juggernauts, something - hopefully - Christensen can avoid.
Good luck, Rick!