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2019-2020 Offseason Pick 5!

Will you be the first to get 3 correct?

Chaim Bloom Press Conference Photo by Billie Weiss/Boston Red Sox/Getty Images

It’s that time of year. No, not the time of year where we watch inferior sports. It’s the time of year where we try to guess who is going to join the Red Sox for the 2020 season. This is obviously a very important tradition on Over The Monster, as it has been run every year since 2011 (except for 2013).

Unfortunately, we kind of suck at it. We have never been able to get anyone with three correct picks. Additionally, the last couple of years, we’ve had a lot of ties.

This year, we will be doing everything we can to eliminate ties. More on that later. First, let’s get into the details of how to participate this year.

How to Participate

Create a post in this thread with the names of 5 players that are not currently with the Red Sox organization. Players can be FAs (excluding those with options on the Red Sox) or under contract with another team (tradeable). Once a set of 5 is posted you cannot chose the same 5 players.

For example: If BobZupcic says “Stephen Strasburg/Anthony Rendon/Gerrit Cole/Scooter Gennett/Yoshitomo Tsutsugo as his five, then .406 cannot choose the same five players. Additionally, you cannot choose those same five players in another order (so no Gerrit Cole/Anthony Rendon/Stephen Strasburg/Scooter Gennett/Yoshitomo Tsutsugo list from .406. From here on out, let’s assume .406 chose the same players, except instead of Tsutsugo, he chose Tetsuto Yamada, and that’s the only difference.

The above rule may confuse someone who wants to choose J.D. Martinez as one of their five.

Addressing J.D., you can select him, but he will only score you a point if he opts out of his contract and signs back with the Red Sox as a Free Agent. You will not score a point if he doesn’t opt out.

You can choose any player under contract with another team. You can choose any player who reaches free agency, including players with options on other teams.

How to Win!

As we go through the offseason and players are acquired by the Red Sox either as FA or via trade you will receive 1 pt for each player of your Pick 5 that makes the opening day 25-man roster.

This year, we will be having multiple tiebreakers, to prevent the cluster of a tie we’ve had in recent years.

Tiebreaker #1 will go to the Pick 5 with the highest overall 2020 salary of properly chosen players.

Tiebreaker #2 will go to the Pick 5 with the highest overall AAV for a single player to sign with the Red Sox. (example - if the Red Sox sign Gerrit Cole and he gets $28 million per year, he will beat Strasburg who got $27 million or whatever it is below 28 million)

Tiebreaker #3 will go to a fill-in question. You will submit your Pick 5 with the answer to this question. The question is: Will Mookie Betts be traded? If yes, to whom? If you do not answer this question, you will be ineligible for TB#3 and all further tiebreakers.

Tiebreaker #4 will go to the Pick 5 that has the lowest salaried player chosen (the inverse of Tiebreaker #2. Yes, you can theoretically have both).

Tiebreaker #5 will go to the Pick 5 that is submitted earliest by time stamp. We are doing this, because we really do not want a tie, and there is more incentive to post later in the cycle to have more information to make your picks. As this is the last tiebreaker, we expect this will not have to be used. It will only be used if we still somehow have a tie after all four other tiebreakers have been used.


Deadline to participate will be November 10th, 2019, at 10 PM ET. We are giving you one week to decide. Yes, this means you could wait until after J.D. Martinez’s opt-out date so you don’t waste a selection on him if you are unsure if he opts out. But you run the risk of your five being chosen by someone else.

Deadline for the contest to end will be the first day of Spring Training. Once Spring Training ends, if a player has not signed, you will not get credit for it, since their market probably exploded.

Past Winners with links (Can anyone guess 3?)

2019 Pick 5 Winners: Chris Sanford, crossedsabres8, Dabageldond, Good_Better_Betts, mattowens04, ty42198, and xii_dex (2)

2018 Pick 5 Winners: Chelista625, Bogey2Short, SirBenjaminPK, Ricochet!, crossedsabres8, REDSOXFAN1973, timtime321 (2)

2017 Pick 5 Winners: sguglie2, titio1300, On to Lansdowne Street (1)

2016 Pick 5 Winner: Rick Bentsen (2)

2015 Pick 5 Winner: RogueNine (2)

2014 Pick 5 Winner: .406 (2)

2013 Pick 5: Pick 5 Writer’s Strike

2012 Pick 5 Winner: aubatron2011 (2)

2011 Pick 5 Winner: mg050369 (2)

TL;DR: To participate, select five players and answer the tiebreaker question. You will have one week to make your selections. Do not duplicate someone else’s list. We will only have one winner. There will not be a tie.

Good luck to everyone!

In the interest of fairness, I will not be making my pick 5 until the very end, after everyone else has picked (because I would easily win the fifth tiebreaker since I’m making the post).