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Fun with OOTP: Jeter and Gehrig face off in upset special

The final batch of first-round matchups also feature the M&M boys of 1961 and 2009’s monster offense

Derek Jeter #2...

We have arrived at the end of the first round of our All-Time Yankees Fantasy Showdown, punctuated by some scrappy underdog performances.

For the uninitiated, we’re using Out of the Park Baseball 21 to stage a simulated tournament between the Yankees’ best teams to see who reigns supreme. You can check out summaries of other first-round action here, here, and here.

Let’s see who will join the field for the second round.

(1) 1961 vs. (8) 2001

The 2001 Yankees were no strangers to postseason drama. They dropped the first two games of the ALDS that year to the Oakland A’s, at home no less. But Game 3 provided the stage for one of Derek Jeter’s most iconic moments, and the Yanks never looked back, winning three straight to advance. Then they batted aside the 116-win Seattle Mariners in the ALCS before falling to the Arizona Diamondbacks in a thrilling seven-game World Series that, disappointment not withstanding, still featured some of the most thrilling moments Yankee Stadium II had ever seen.

But in this series, they stood opposite to one of the most iconic teams in franchise history — the ’61 Yanks, featuring the M&M boys, Mickey Mantle and Roger Maris.


Sixty-one got off on the right foot, cruising to a 3-0 Game 1 victory behind a silky starting performance from Whitey Ford. They followed it up with two more wins to give themselves a stranglehold on the series, but 2001 wouldn’t exit the stage without a fight. Third baseman Scott Brosius kept them alive with a four-hit, four-RBI performance in a 7-5 Game 4 win. Down 4-1 in the bottom of the eighth inning of Game 5, the ’01 squad rallied for four runs to win 5-4 and force a Game 6.

Did they have enough mojo to pull off an epic comeback? Unfortunately for them, not quite. (Come on, 1961’s not blowing a 3-0 series lead).

A Mickey Mantle sac fly in the fourth inning of Game 6 was all ’61 would need as they clinched the series with a 1-0 victory. Mantle’s .409 batting average, one homer and five RBI were good for MVP honors.

1961 wins 4-2.


(4) 2009 vs. (5) 1949

Man, the 2009 Yankees’ offense was deep. Their go-to lineup featured eight players with an OPS+ of 115 or better. (The only one who fell short was Melky Cabrera at 93.) And they had a revamped pitching staff led by new signing CC Sabathia.

The ’49 team was, of course, no lightweight, featuring Joe DiMaggio, Yogi Berra and Phil Rizzuto. They were the vanguards of the franchise’s second streak of five consecutive World Series wins.


Game 1 was a heavyweight bout. After trading jabs in the first four innings, the ’09 Yanks exploded for seven runs in the bottom of the fifth, helped along by a rare Joe DiMaggio error in center field. Melky Cabrera ended up as the prime beneficiary, blasting a grand slam later in the inning off Fred Sanford. The 2009 team went on to win 13-7.

In Game 2, however, Berra smacked a three-run homer to break up a 2-2 tie in the top of the 12th inning, powering ’49 to a 5-2 win. The two squads traded wins in Games 3 and 4, setting the scene for a pivotal fifth game. CC Sabathia didn’t disappoint, tossing eight shutout innings en route to a 4-0 victory for his ’09 squad. They coasted to another shutout win in Game 6, 6-0, behind the pitching of Andy Pettitte and Sergio Mitre. Johnny Damon, who hit .400 with two homers and five RBI, was named MVP.

2009 wins 4-2.


(3) 1938 vs. (6) 1977

The 1977 Yankees entered the series as the last ‘70s-era team standing in this tournament, so their era’s fate rested on their shoulders. But to survive, they’d need to outlast Lou Gehrig, Joe DiMaggio, Bill Dickey and Joe Gordon.

Game 1 was a 13-inning nailbiter. With the score tied 2-2 in the top of the 12th, Thurman Munson stroked a two-out RBI single to give 1977 the lead. They asked closer Sparky Lyle to seal the victory, but he was entering his third inning of work and promptly gave up a leadoff single to Gehrig, followed by a double to Tommy Henrich, which scored “The Iron Horse.” Catfish Hunter came on in relief and wiggled out of trouble, but in the next inning, DiMaggio absolutely crushed a mammoth 461-foot walkoff homer to left-center off the righthander, handing ’38 a 1-0 series lead.


A 4-3 win in Game 2 followed for ’38, before 1977 answered back with two wins of their own. But the ’38 offense couldn’t be contained in Game 5, as they torched ’77 starter Ron Guidry for six runs en route to a 9-5 win. A resounding 9-1 win for 1938 followed in Game 6, clinching the series and officially killing the 1970s.

Lou Gehrig hit three home runs and drove in four to earn MVP honors.

1938 wins 4-2.


(2) 1936 vs. (7) 1999

I mentioned earlier that the 1949 team kicked off a string of five straight World Series wins, the franchise’s second such streak. Well the 1936 team plowed the road for the club’s first five-title victory parade. Like other teams of its era, the 1936 edition was powered by Gehrig and DiMaggio, who was then a precocious rookie.

The 1999 team, on the other hand, was driven largely by its pitching staff. David Cone, Andy Pettitte and “El Duque” Orlando Hernandez were joined by newcomer, and reigning Cy Young winner, Roger Clemens. It also boasted perhaps the finest season of Derek Jeter’s career.


It was a topsy-turvy series. The underdog 1999 team drew first blood with a 10-4 Game 1 victory, then stepped on the necks of their ’36 counterparts as they won the next two games to take a 3-0 series lead. Thirty-six wouldn’t stay on the mats forever, though, striking back with their own streak of three wins, including a 15-inning thriller in Game 5. That set the stage for a decisive Game 7. With the game tied 4-4 in the top of the eighth inning, catcher Jorge Posada stepped up to the plate against Red Ruffing with the bases loaded and promptly unloaded them with a three-run double. The 1999 squad closed out a 7-5 win to eke into the next round.

Jeter, who hit .333 with a homer and seven RBI, was named MVP.

1999 wins 4-3.