2017 - 2019: Matt goes back-to-back, Jack S represents younger generation


Matt Smith, who had never finished higher than third - but finished in third four times - rang the bell for the first time in 2017. Matt beat out older brother Tom Jr., who finished in 2nd, while budding rivals Austin Haskell and Jack Sullivan finished 3-4. Husband-and-wife team Sandra Smith and Tom Smith Sr. finished 5-6.


With Tom Jr. holding on to a trade until nearly the last minute, younger brother Matt Smith stayed paranoid until the end, but wound up with a convincing victory - a 6.44% margin, good for 5th all-time, and the most since Sandra Smith's legendary victory over her husband Tom Sr. in 2006.

This was the second year in a row that Matt and his brother Tom Jr. finished first and second.

And, it had been fourteen years since the League had had a repeat champion. Way back in 2003-2004, the first years of the League, Matt's father Tom Sr. won back-to-back.

Notably, Sandra Smith finished 3rd, marking the 4th year in a row that she finished in the top 5.


Wow, what an end to the 2019 season. In one of the most exciting finishes in league history, Jack Sullivan traded first place with his grandfather, Tom Smith Sr., throughout the last weeks of the season. As Jack’s father Ray noted, a walk-off hit by the great Rafael Devers on the last day of the season helped Jack fend off his conniving grandfather and take first place by only 5 points. It was the second-closest finish in League history, behind Shannon Sullivan's 2001 defeat of Tom Jr.

At the age of ~22, Jack becomes the second-youngest owner to ever win the league, behind Austin Haskell, who won the league in 2014 at the age of ~20. This continues a nice rivalry in the “great-grandchildren” generation of Diffendorfs: Jack finished 2nd in 2013, Austin finished 1st in 2014, Austin and Jack finished 3-4 in 2017, Austin finished 6th in 2018, Jack finished first in 2019. So far their rivalry has been much more civil than their legendary grandfathers’, but perhaps age will introduce some bitterness.

Getting back to 2019: Gayle Diffendorf shrewdly picked up rookie phenom Peter Alonso - who no one else picked - to solidify her hold on 3rd place. Mick Sullivan couldn’t quite keep pace with his older brother Jack, but turned in a solid season at 4th place. Tony Burns, no stranger to the top 10, finished 5th.

Matt Smith, the winner of the previous two seasons (just ask him) sailed through most of the season firmly in first place again, but dropped like a stone in August and barely held on to the last money spot (6th).

Sam Smith had a very respectable finish in 7th, and may have overtaken his uncle Matt if not for a panicky early-season benching of Brock Holt.

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