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So as we head into trading season the question that comes up is what did the Jays do in other years when they contended? What did they give up, what did they get back? Did it work?

For sake of argument we'll say it worked in '85, '91, '92, '93, '15, '16, '22, '23 as they made the playoffs all those years. Super worked in '92, '93 as they won the WS those years, '15, '16 also saw them win some division series. I ignored the bizarre 2020 season (non-standard deadline, short season, so many weird things) at first, but added after a request (why not?) all deals were August 27-30th that year. I'm using July 15-August 5th as the trade deadline, but will see if other significant trades happened close to that range (July 1st to August 31st). I'll try to avoid minor leaguer for minor leaguer trades (ie: for AAAA types to fill in depth stuff).

YearTraded awayReceivedWAR awayWAR hereNotes
2023 Trent Thornton Mason McCoy 0.1 0.0

Sem RobberseAdam Kloffenstein Jordan Hicks --, 0.1 (1 game) 0.5 Good catch dalimon5

Sammy Hernandez Génesis Cabrera -- 0.1 -0.2 for Cabrera post Toronto

Matt Svanson Paul DeJong + cash 0.3 -0.8 0.5 post Toronto for DeJong
2022 Moises BritoNick Frasso Mitch WhiteAlex De Jesus --, -- -1.6, --

Jordan Groshans Anthony BassZach PopEdward Duran -0.1 1.5, -1.2, --

Max CastilloSamad Taylor Whit Merrifield -0.5, -0.2 0.8
2021 Rowdy Tellez Bowden FrancisTrevor Richards -0.5 (0.5) 1.7, -0.8 July 6th

Riley Adams Brad Hand 1.8 -0.6

Yaifer PerdomoJ.J. D'Orazio Joakim Soria --, -- -0.3

Austin Martin, Simeon Woods Richardson  José Berríos -1.0, 2.6 7.3 (0.9) Berrios 0.9 is for 1st year+
2020 Griffin Conine Jonathan Villar  --  -0.2 Good idea to add back in hypobole

Kendall Williams, Ryan Noda Ross Stripling --,  1.3 (1.6) 3.7 (2+ years) 
  Travis Bergen Robbie Ray & cash 0.7 (0.1)  7.1 (0.2) Bergen did the extra 0.6 here the next year, Ray became a free agent and resigned here for 1 year
  Alberto Rodriguez Taijuan Walker  -- 1.0 
2016 Drew Storen Joaquín Benoit 0.1 1.4

Hansel Rodriguez B.J. Upton + cash -- -0.5

Jesse Chavez Mike Bolsinger 9.0 (2.5) -0.5

Lupe Chavez Scott Feldman -- -0.6

Drew Hutchison Francisco Liriano, Reese McGuire, Harold Ramírez 0.1 0.4, 1.1, -- Liriano traded later for Teoscar
2015 Miguel Castro, Jeff Hoffman, José Reyes, Jesús Tinoco LaTroy Hawkins, Troy Tulowitzki 3.2 (-0.4), 3.6 (-1.5), -0.3, 1.8 (0.2) 0.1, 5.2

Matthew Boyd, Jairo Labourt, Daniel Norris David Price 11.8 (9.3), 0.1, 4.9 (6.5) 2.6 23 IP in playoffs, 16 ER allowed

Nick Wells, Jake Brentz, Rob Rasmussen Mark Lowe --, -0.9, -1.1 0.1

Alberto Tirado, Jimmy Cordero Ben Revere --, 0.6 0.7
2006 Vinnie Chulk, Shea Hillenbrand Jeremy Accardo 0.9 (2+ yrs), -0.6 1.8 (4+ years)
2000 Darwin Cubillán, Michael Young Esteban Loaiza -0.2, 24.7 (25.9, 14.1 1st 6 years) 3.7

John Sneed Rob Ducey -- -0.2

Brent Abernathy Mark Guthrie, Steve Trachsel 0 (1.0) 0.2, 0.8

Peter Munro Dave Martinez 1.1 0.8 Aug 4th

Rob Ducey Mickey Morandini 0.3 -0.2 Aug 5th
1999 Pat Lynch Brian McRae -- -0.3 Aug 9th
1993 José HerreraSteve Karsay Rickey Henderson -0.7, 11.1 (2.4) 0.5
1992 Rob Ducey, Greg Myers Mark Eichhorn 2.4 (-0.5), 6.5 (0.9) 1.7

Ryan ThompsonJeff Kent  David Cone 3.5 (3.4), 54.2 (8.4) 1.6 Aug 27th
1991 Steve WapnickShawn Jeter Cory Snyder 0.0, -0.3 -0.7

Bob WishnevskiWilliam Suero Candy Maldonado --, 0.0 3.8 (1+ years) Aug 9th
1990 Nelson Liriano, Pedro Muñoz John Candelaria 0.8 (0.9), -1.3 -0.2

Mauro Gozzo Steve Cummings Alex Sanchez Bud Black -1.0, --, -- 0.2
1989 Mike Brady, Jeff Musselman Mookie Wilson --,-0.5 1.5 (2+ years)

Francisco Cabrera, Tony Castillo Jim Acker 0.5, 6.8 (-0.3) 0.3 (2+ years) Aug 24th
1988 No trades at all this calendar year  


1987 Luis Aquino Juan Beníquez 10.7 (8.0) 0.2 (1+ years) July 14th

Darryl LandrumDon Gordon Phil Niekro -0.4 -0.3 Aug 9th

Oswaldo PerazaJosé Mesa Mike Flanagan -1.1, 11.4 (-0.9) 4.1 3+ years Aug 31st
1985 Len Matuszek Al Oliver 1.0 (2+ years) -0.6 July 9th

Matt Williams, Jeff Mays, Greg Ferlenda Cliff Johnson 0.9, --, -- 0.8 over 1+ years Aug 28th

Note: No trades in 1983 or 1984 or 1986 as all 3 years few thought the Jays still had a shot come August 1st.  Pre 1994 was all Pat Gillick, 1999 + 2000 was Gord Ash dreaming in technocolor, 2006 was JPR doing a deal while 5 1/2 out, 2015 was AA's only contending year, 2016 and beyond were the current crew.

In brackets I added WAR for the team they were traded to if they had significant time elsewhere post Jays (WAR listed is post Jays or as a Jay depending on situation).  So in all those years of contention and many trades the biggest losses were Jose Mesa (who didn't become good until he switched teams again), Luis Aquino, Jeff Kent (mostly after he left the Mets), Steve Karsay (again, post leaving the team he was traded to), Michael Young (the biggest loss outside of Kent), Matt Boyd, and Jesse Chavez (again mostly post team he was traded to).  Mid-season trades have only really cost big time with one guy then (with what he did at the team he was traded to) and that was Michael Young by good ol' Gord Ash (no bad deal list is complete without Ash being mentioned).

Contending trades: Atkins: 20 deals, leading to 3 playoff appearances and 1 oh so close. AA: 4 deals, 1 playoff in the only year he made mid-season adds. JPR 1 deal, 0 playoffs in 1 sorta try. Ash 6 deals, 0 playoffs in 2 tries. Gillick: 14 deals, 5 playoffs, 2 WS titles, twice not making playoffs.

Going by pure WAR (not a good method) the Jays 'won' 23 of these 46 trades - better than expected given how often they were 'potential' for under 1/2 a season.  I only counted WAR for the team they were traded to, or for their first 6 full years there (Michael Young) as otherwise the WAR totals would be silly for guys like Mesa, Kent & Young when they did a lot post their first 6 years.  Net total WAR was 61.5 given up for 35.0 returned, resulting in 10 playoffs and 2 WS titles (both heavily impacted by trades mid-season).  Looking through you can see LOTS of flops, and just a few guys who blossomed away from Toronto (Kent, Young, Mesa, Aquino, Karsay, Boyd, Jesse Chavez).  A few showed hope post Toronto like Tellez but flopped shortly after that hope (sucks as I am a fan of Tellez).

If anyone can think of other trades that should count please mention it in the comments.  I tried to catch everything that was July/August ignoring September trades (not qualified for playoffs) and June/earlier (too soon to count as deadline deal imo).  I looked at other years just in case the team did deals to try to sneak in but didn't see anything beyond dumps (1998 and 2024 being the biggest ones). 1984/1983 were the first years in contention but Gillick didn't feel it was the right time to deal I guess (both years some relief help would've gone a long way to helping).
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dalimon5 - Saturday, July 05 2025 @ 12:44 PM EDT (#463079) #
Nice summary John. I think you're missing the Jordan Hicks trade though.
hypobole - Saturday, July 05 2025 @ 02:23 PM EDT (#463083) #
2020 - Walker, Stripling, Ray and Villar. I'm rarely opinionated about trades as I usually give the benefit of the doubt to the FO, but the one trade I hated at the time was the Villar deal, and not because of Conine who I agreed with almost everybody that his K issues would be a killer. Villar was a bad makeup player who the Marlins were more than happy to get rid of. Our FO got what they deserved
John Northey - Saturday, July 05 2025 @ 02:47 PM EDT (#463087) #
2020 was a weird one which is why I didn't list it. Maybe I should add it in though. As to Hicks I could've sworn I had it in there. I'll add it back in.
John Northey - Saturday, July 05 2025 @ 03:11 PM EDT (#463088) #
Basically, from how these have worked out you can expect a 50-50 result for net WAR lost vs gained, but likely to lose twice as much WAR as gained since any WAR gained will mostly be for 2025 (thus of high value towards making the playoffs) vs future value (lord knows the situation then).  1992's loss of Kent hurt a bit after '92 but not much (in '93 the only year that mattered post 92, he was worth only 0.3 WAR as a full time 2B - if signed long term he'd have been very helpful in 2000 and might have saved Ash's job with a 7 WAR season but would've he had that without being in SF with Bonds & BALCO?  Who knows?).  Michael Young would've helped make the 2000's a bit less depressing, but his best chance to help would've been 2006 probably (3.8 WAR) but the Jays were out of the playoffs by 8 games that year (as close as they'd get in JPR's time).  Boy, forgot how far out the Jays were in the 00's - they never were close at the end.
Marc Hulet - Saturday, July 05 2025 @ 08:32 PM EDT (#463120) #
How about a trade with the Pirates: David Bednar (high leverage arm), Caleb Ferguson (lefty with good stuff and playoff experience) and Ke'Bryan Hayes (Gold Glove 3B defence and take his remaining contract off their hands) for Khal Stephen, Alan Roden, and Ryan Jennings.

Two years of Bednar, 4 years of Hayes, and Ferguson is a pending FA. Pirates get two prospects close to MLB-ready and an arrow up starting prospect nearing AA.

Hayes doesn't cost a fortune if the Jays can't "Popkins" his bat and gives an IF option if Bichette leaves.
dalimon5 - Saturday, July 05 2025 @ 08:59 PM EDT (#463122) #
That's an intriguing proposal.
Glevin - Saturday, July 05 2025 @ 09:29 PM EDT (#463124) #
Don't want Hayes. Think Gimenez, Clement, and Barger is fine for IF. Adding another great D, horrible offense guy doesn't make sense to me. Bednar would be a good addition though.
John Northey - Sunday, July 06 2025 @ 01:45 AM EDT (#463134) #
An interesting trade proposal Marc. David Bednar would be a GREAT addition to the pen (killer 1/2 punch at the end of games), Caleb Ferguson also would be a positive (give Little a bit of rest), but Ke'Bryan Hayes is more ballast to cut the prospect cost. Hayes is a pure defense guy (lifetime 86 wRC+) without the 'wow' year that Gimenez has. As a RH hitter he would be able to platoon with Barger but then you gotta figure out where to put Clement. Odds are he'd take over the 5th IF role instead (go to 3B when someone needs a day off with Clement going to the other position, thus giving a killer infield defense all the time) - he is sub $10 mil for 4 more years so not a killer to the budget (just a touch more than Straw).

Khal Stephen scares me to trade as he looks damn good this year but is 22 in A/A+ so might not be as good as he seems (pitchers are so damn hard to predict), Alan Roden would help Pittsburgh right away and not hurt the Jays given the depth in the OF, and Ryan Jennings is 26 in AAA in the pen, thus a meh to me (very wild, lots of K's, lots of walks). Anyone 26+ in the minors I won't worry about losing in a trade.
99BlueJaysWay - Monday, July 07 2025 @ 06:18 PM EDT (#463202) #
Thanks John! I forgot how successful the 2020 deadline was.

I’m really looking forward to this deadline. I’m hoping for a surprise and an elite starter. Fingers crossed!
John Northey - Monday, July 07 2025 @ 11:29 PM EDT (#463221) #
In the past we've seen 2-4 trades when contending, but this year I'm expecting the low end, 1 or 2 trades. Not a lot of upgrading possible right now, with the injuries coming back and the like where do you improve? 1 more reliever (ideally a LHP) would be nice, but where else? Checking WAR by primary position...
  • C: Kirk is #3 in MLB for WAR as a C
  • 1B: Vlad is #5 for 1B
  • 2B: Gimenez is #20 at 2B (ick)
  • 3B: Clement is #8, Barger #12
  • SS: Bo is #21 (ick) but ain't going anywhere
  • LF: Lukes is #28, Schneider #31, Roden #45
  • CF: Lukes is #24, Straw #26, Varsho #28 (his pace would be top 10 if healthy)
  • RF: Barger #8, Springer #11
  • DH: Springer #6
Fully healthy it is Kirk-Vlad-Gimenez-Clement-Bo-Santander-Varsho-Barger-Springer with a bench of Lukes-Straw-Schneider-Heineman (#14 at C, doing better on a per-game basis than Kirk) probably. Or Wagner for Schneider. After today I suspect Loperfido is making a case to be kept around too.

Overall WAR by position for the Jays rank 2-7-9-7-17 (SS)-16 (LF)-12-14-12, so bottom half only at SS and LF, close in RF but improving with Barger. Top 10 C/1B/2B/3B, never bottom 10. For hitters the Jays are 3rd best in MLB since June 1st (Tigers, Cubs barely ahead). Since June 1st starting pitchers are 16th (acceptable), relievers 22nd (surprising, 5 guys at -0.2 fWAR in that window in Swanson, Green, Sandlin, Fluharty, and Garcia)

Basically relief help is most needed, followed by Varsho coming back and stabilizing the OF imo. That cuts trades down - can't see where in the lineup you'd add another player, an ace for the rotation would be nice but near impossible to get.
scottt - Friday, July 11 2025 @ 08:58 AM EDT (#463402) #
Bolsinger's career ended in a trash can game in Houston. He sued the Astros but got thrown out of court.  What he really acquired at the deadline?
scottt - Friday, July 11 2025 @ 08:59 AM EDT (#463403) #
Benoit was untouchable but got injured getting of the bench during a brawl.
scottt - Friday, July 11 2025 @ 09:01 AM EDT (#463404) #
I totally hated getting guys having bad year like Hand and DeJong.
It did work with Grilli.
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