In one of the best games of the 2024 playoffs, Jack Shack took an early lead, Shady Characters later pulled ahead, Jack Shack reclaimed the lead, Shady Characters jumped in front again, Jack Shack evened things up in the sixth, and Billy put Shady Characters a game away from a four-peat with a walk-off solo homer to lead off the bottom of the sixth inning. In a thrilling 6-5 win, Shady Characters took their first series lead with their second consecutive win, moving ahead 3-2 in the best-of-five Wiffle Series with two chances to earn a fourth consecutive championship in games 6 and 7 (if necessary). In addition to the walk-off homer, Billy had three singles and scored a run, and Nate, Thomas, and Lucas each delivered two hits to overcome four doubles from Josh and three runs scored from Jacob. Jack Shack will need a win in game six to remain alive and force a pivotal and decisive game seven.
Tom took the mound for Shady Characters and after striking out Josh to start the game, he allowed a one-out double to Jon M. Tom retired Ryan, however, stranding the runner and ending the inning.
Jon M started for Jack Shack after earning victories in games one and three with dominant outings that quieted the vaunted Shady Characters offense. He allowed a leadoff single to Billy to start the bottom of the first, but stranded him, retiring Nate and Thomas to end the inning.
Jon D led off the top of the second with a double, and he scored when Jacob followed with an RBI single, putting Jack Shack up 1-0. Josh then doubled, scoring Jacob, and Jack Shack led 2-0. Jon M followed with his second double in as many innings, scoring Josh, and Jack Shack had opened up a 3-0 lead. The first four Jack Shack batters had reached base safely to start the second inning, and it looked as if they would blow the game open, but Tom cracked down. He retired Ryan and Jon D to strand Jon M at second, ending the inning, and Shady Characters trailed by three runs.
Jon M rolled through the bottom of the second, retiring Tom and Lucas in order.
Josh hit a one-out double in the top of the third, but Tom stranded him, retiring Jon M to end the inning, and the score remained 3-0.
Jon M retired Billy to start the bottom of the third, and Nate followed with a one-out triple, Thomas put Shady Characters on the board with a two-run homer, cutting the deficit to 3-2. Jon M retired Tom to end the inning, and Jack Shack led by a run.
Tom cruised through the top of the fourth, sending Ryan and Jon D down consecutively.
Lucas led off the bottom of the fourth with a single, and he moved from first to third when Billy followed with a single. Two batters later, with one out and runners on the corners, Thomas singled, scoring Lucas to tie the game at 3-3. Shady Characters once again had runners on the corners with one out, but Jon M avoided further damage, striking out Tom to strand both runners and end the inning.

Billy went 4-for-5 in game five and his walk-off solo homer in the bottom of the sixth put Shady Characters a win away from another championship
Jacob led off the top of the fifth with a double, and Josh followed with an RBI double to score him, putting Jack Shack back in front 4-3. Tom retired Jon M and Ryan to strand Josh at second, ending the inning, and Shady Characters trailed by a run.
Lucas started the bottom of the fifth with a double, putting the tying run in scoring position. Billy followed with an RBI single to score him, and the game was tied at 4-4. Nate singled, putting runners on the corners. Two batters later, with one out, Tom hit an RBI single to score Billy, and Shady Characters once again led 5-4. Shady Characters had runners on first and third with one out, but Jon M stranded both runners, retiring Lucas to end the inning, and Jack Shack would need a run in the top of the sixth.
Tom remained on the mound to close things out for Shady Characters. He retired the first batter he faced, putting Shady Characters an out away from victory. With the game on the line, Jacob came to the plate and launched a solo homer, tying the score at 5-5. Josh followed with his fourth consecutive double, putting the go-ahead run in scoring position. Tom and Shady Characters elected to intentionally walk Jon M, putting two runners on with one out. Tom faced Ryan, and the strategy worked. He got him to fly out to the mound, stranding both runners, and the game was tied heading into the bottom of the sixth.

Jack Shack celebrate at the plate after Jacob’s solo homer with one out in the top of the sixth tied the game and kept his team alive in game five
Jon M also remained on the mound for Jack Shack. He had pitched very effectively through games one and three, but his luck ran out in game five. The first batter he faced in the bottom of the sixth, Billy, launched a homer to deep left-center, giving Shady Characters a 6-5 win in game five and putting Shady Characters a game away from another title.
The walk-off homer and win gave Shady Characters a 3-2 lead in the best-of-seven Wiffle Series.
W: Tom (3-3)
L: Jon M (3-1)
Game Notes:
– Tom pitched the complete game win for Shady Characters, allowing five runs on ten hits and striking out one.
– Jon M took the loss in a complete game effort for Jack Shack, giving up six runs on eleven hits and striking out one in five innings.
– Billy led Shady Characters on offense, going 4-for-5 with three singles, the game-winning walk-off homer, two runs scored, and two RBI. His walkoff homer was the 18th in EWL playoff history, and the first since his teammate Tom hit one in the 2022 playoffs.
– Nate, Thomas, and Lucas each went 2-for-4 in the Shady Characters win. Nate had a single, a triple, and a run scored. Thomas had a single, a homer, a run scored, and three RBI. And Lucas had a single, a double, and two runs scored.
– Josh led Jack Shack in the loss, going 4-for-5 with four doubles, a run scored, and two RBI.
– Jacob also went 3-for-4 in the Jack Shack loss with a single, a double, a home run, three runs scored, and two RBI.


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