TORONTO — Over the course of 43 years, there’s going to be some good, some bad and, hopefully, if you’re lucky as a franchise, some great.

Since 1977, the Toronto Blue Jays have without a doubt had a mixture of all three, with some good currently on the way if things break right.

The history of free-agent signings and lucrative extensions that helped build those ballclubs of varying degrees of success mirrors the eventual overall outcomes.

Six men have held the title of Blue Jays general manager in franchise history — technically it’s seven, but Tony LaCava’s short stint in 2015 was an interim tag — but one of them built a resume above all others: Pat Gillick, the architect of those great Blue Jays teams and an era of winning that has proven hard to match.

Peter Bavasi (1977) before him, and Gord Ash (1995-2001), J.P. Ricciardi (2002-09), Alex Anthopoulos (2010-15) and Ross Atkins after him, have all tried and failed to replicate that magic in the years since.

Repeatedly make smart moves in free agency, and things have a tendency to turn out well.

Gillick knows that. Spending money was what put his teams over the top in the 1990s.

Swing and miss with your employer’s money and it usually ends poorly – both on the field and in tenure. Anyone who experienced the 2000s as a Blue Jays fan will attest to that.

Over the course of this nine-part series that will take a look at the best and worst in Blue Jays history, we’ll eventually get to the good and bad of three different ways those GMs went about building the teams on the field, starting with the best and worst signings today, followed by trades and draft picks in the coming days.

This list is made up of work in free agency, so you won’t find Jose Bautista’s contract extension prior the 2011 season, Joe Carter’s re-signing in the winter of 1992, or Anthopoulos’ $3.9-million coup to get Vladimir Guerrero Jr. to sign as an amateur international free agent in 2015.

There is a lone exception, a mid-2000s extension that was too egregious to ignore.​


The Best and Worst of the Blue Jays on

Mon, April 6 – The five best and worst signings

Wed, April 8 – The five best and worst outfielders

Fri, April 10 – The five best and worst games

Mon, April 13 – The five best and worst trades

Wed, April 15 – The five best and worst infielders

Fri, April 17 – The five best and worst seasons

Mon, April 20 – The five best and worst draft picks

Wed, April 22 – The five best and worst pitchers

Fri, April 24 – The five best and worst moments



5. (TIE) Dave Stewart: Two years, $8.5 million on Dec. 8, 1992; Jose Canseco: One year, $2.125 million on Feb. 4, 1998

Embedded ImageYou’ll notice I cheated away some hard decisions on a few of these lists by using fifth-place ties. No gimmicky shootouts here, just credit where credit’s due.

These two signings couldn’t be more different in terms of defining why I’ve deemed them quote, unquote “successful.”

After the Jays eliminated Stewart’s Oakland Athletics in 1992, they stole Stewart away in free agency a couple months later in December, signing the righty with the intimidating stare to a two-year deal.

In his age-36 season in 1993, Stewart was no longer a top-of-the-rotation force, posting a 12-8 record and a 4.44 ERA in 26 starts, third on the staff behind Pat Hentgen’s 3.88 mark and Juan Guzman’s 3.99 ERA.

But the postseason is where Stewart recaptured his past glory, winning ALCS MVP by allowing just three earned runs over two starts in Games 2 and 6 against the Chicago White Sox.

While he didn’t pitch well in the World Series against the Philadelphia Phillies, he was able to keep his team in the game long enough in Game 6, allowing four earned runs over six innings, to let Joe Carter do his thing in the ninth inning.

Stewart was pretty terrible in the final year of the deal in 1994, but he had earned his money.

Canseco earned his money and spot on this list in a much different way, rebounding from six straight seasons of 119 games or less — in most cases, many less — to amazingly play 151 games in 1998 on a one-year deal from Ash that ended up netting him $2.125 million when all was said and done.

Of course, the Jays only won 88 games that year and finished third in the division, while Canseco was worth just 1.3 fWAR thanks to no defence, leading the league in strikeouts, and a low on-base percentage, but, but, but ... when it comes down to it this sport is about entertainment, and Canseco crushing 46 homers, stealing 29 bases (he was caught a laughable 17 times) and putting together the healthiest season since his Bash Brothers heyday was at least fun – steroids or no steroids.

He was still worth more than a couple million bucks and fans definitely got their money’s worth.


4. Dave Winfield: One year, $2.3 million on Dec. 19, 1991

Brought in as a 40-year-old to help lengthen the Jays’ lineup and provide a presence, Winfield answered the call, slashing .290/.377/.491 with 26 homers and 108 RBI in his swan song as a productive major leaguer.

Going by fWAR, the 3.8 mark he posted in 1992 makes it Winfield’s sixth-best season in his storied 22-year career.

He also provided some Fall Classic heroics, delivering a game-winning two-run double in the 11th inning of Game 6 against the Atlanta Braves.


3. Jack Morris: Two years, $10.85 million on Dec. 18, 1991

Embedded ImageLosing the 1991 ALCS to the Minnesota Twins led Gillick to go out and steal their ace, inking the 37-year-old Morris one day before signing Winfield.

All Morris did in the twilight of his career in his first year in Toronto was finish fifth in the AL Cy Young race with a 21-6 record and a 4.04 ERA.

In completely opposite fashion of Stewart, Morris was great in the regular season but terrible in the postseason, allowing an ugly 19 earned runs over two so-so starts and a pair of awful outings, including one in Game 5 of the World Series.

Just like Stewart, though, Morris cratered in the second and final year of the deal, registering a 6.19 ERA, and he did not pitch in the postseason due to injury.


2. Paul Molitor: Three years, $13 million on Dec. 7, 1992

Aging well into his mid-30s when Gillick tabled him a lucrative three-year pact, the long-time Milwaukee Brewers star went out and delivered in 1993, slashing .332/.402/.509 with a career-high 22 homers to help lead the Jays’ potent lineup to 847 runs scored, third-best in baseball.

Molitor poured it on in the postseason with 21 hits and a .447 average to lock up World Series MVP honours, before batting .341 in 1994.


1. Roger Clemens: Four years, $40 million on Dec. 13, 1996

Embedded ImageWith Boston Red Sox GM Dan Duquette believing Clemens was done in the winter of 1996, Ash swooped in with a four-year, $40-million offer that turned out to be a major bargain.

Removing the emotions of the way he left town and the steroid allegations years later, Clemens was simply dominant during his two years in Toronto, running up a 41-13 record and a stingy 2.33 ERA across 67 starts and an astounding 498.2 innings.

The 1996 and ’97 seasons were worth a combined 18.9 fWAR and produced back-to-back Cy Young Awards, two of the four in the Blue Jays’ trophy case to this day.


Embedded Image5. Corey Koskie: Three years, $17 million on Dec. 14, 2004

Watching homegrown star Carlos Delgado walk as a free agent — he signed with the Marlins for $52 million over four years — and replacing him, in part, with Canadian third baseman Corey Koskie did not work out for Ricciardi.

A well-rounded player with the Twins, the Manitoba product suffered through an injury-plagued debut season with the Jays in 2005, struggling to a .249/.337/.398 slash line in just 97 games.

The Troy Glaus acquisition the following off-season sealed Koskie’s fate at the hot corner in Toronto, and the remainder of his contract was shipped to the Brewers for pitcher Brian Wolfe, who threw 82.2 innings of unremarkable relief for the Jays over the next three seasons.

The Jays also sent $7.1 million to the Brew Crew to take Koskie off their hands.

Koskie retired in 2009 due to the effects of post-concussion syndrome after being hurt in a fall while chasing a pop-up in a game on July 5, 2006.


4. Ken Dayley: Three years, $6.3 million on Nov. 26, 1990

The reason Dayley’s acquisition got attention — still gets, I guess, since I’m writing this — is the fact it was Gillick’s first major foray into free agency as the years of near misses in the AL East started to pile up in the late '80s and into the 1990s.

Dayley, a 32-year-old left-handed reliever who had been the third-overall pick in the 1980 draft, was coming off six straight years of above-average-to-solid work in the St. Louis Cardinals bullpen when Gillick handed him $6.3 million to be a key relief cog for the Jays.

What Dayley ending up giving them, however, due to various injuries and a bout with vertigo, was just five innings over the next three seasons.

It’s not the most lucrative deal on this list even when you consider how much the sport’s financial landscape has changed, but they could’ve set the cash on fire and it would’ve been the same return.


3. Erik Hanson: Three years, $9.4 million on Dec. 22, 1995

Embedded ImageHanson parlayed a 15-5 season, a 4.24 ERA, and 4.1 fWAR with the Red Sox in 1995 into a three-year pact from Ash, who was trying to rebuild the Jays after Gillick’s exit.

Hanson was ... not good.

While he was able to at least be available for Jays manager Cito Gaston every fifth day, making 35 starts and throwing 214.2 innings, Hanson was clocked for 243 hits and a 5.41 ERA, leading to a 13-17 record.

His 3.0 fWAR shows there’s value to being able to amass innings, but Hanson completely fell on his face in the final two years of the deal, making only 10 more starts and finishing with a 5.68 ERA as a Blue Jay.


2. Vernon Wells: Seven-year, $126-million extension on Dec. 15, 2006

It was supposed to be an exciting day when the Jays signed Wells, their franchise cornerstone, to a seven-year, $126-million extension that made him the richest player in franchise history.

After all, Wells was coming off a 2006 season that catapulted him into the league’s elite, a monster 5.8 fWAR year with a .303/.357/.542 slash line, 32 homers and 17 steals.

But with the ink still drying on the contract Ricciardi gave him, the wheels fell off and Wells went from a burgeoning start at the age of 27 to a flawed player who couldn’t get on base enough and was declining defensively in centre field.

Over the next three seasons, Wells was worth a total of 2.7 fWAR and hit 16, 20, and 15 home runs, respectively.

The contract quickly became a burden and was viewed as one of the worst in baseball.

A 31-homer bounce back in 2010 shockingly allowed Anthopoulos to unload Wells and the nearly $90 million remaining on his deal in January of 2011, and he’d end up getting paid $21 million for the 2014 season despite not playing a game after being released by the Yankees in January.

While we’re at it, the 2008 extension Ricciardi handed outfielder Alex Rios didn’t work out much better, and only a Chicago White Sox waiver claim allowed them to escape the nearly $60 million owing on that one.


1. B.J. Ryan: Five years, $47 million on Nov. 29, 2005

Embedded ImageThese days, contenders would salivate over the prospect of a left-handed power reliever coming off a 2.43 ERA and 2.6 fWAR being a free agent, as Ryan was after the 2005 season.

But even now, 15 years later, both the term and the total value of the largest contract ever handed to a closer at the time would be a bit much.

While it’s easy to forget Ryan was lights-out dominant in his first season in Toronto, saving 38 games with a minuscule 1.37 ERA, it was mostly downhill from there and the final four years of Ryan’s deal provided zero value.

Tommy John surgery got in the way in 2007, but he struggled with control when he returned and was eventually released in July of 2009, collecting $10 million from the Jays to not pitch in 2010.

All told, the Jays got 155.1 innings and 75 saves out of Ryan in exchange for $47 million.​