PUKE! Worst Endings to Historic Careers Ever, Ranked
WSD Note - this was written by Dante, long time friend of the program. He worked his dick off on this and there wouldn't be a Barstool Chicago without him. I just read the entire thing and it did, in fact, make me wanna puke as a sports fan. Dante's a huge Pats fan, so Brady going to Tampa was a real kick in the nuts for him
Yesterday was a rough one. On top of the worldwide pandemic, waking up and seeing Tom Brady announce he’d no longer be a New England Patriot, I, like millions of others around the globe, felt somebody had knocked the wind out of me. It’s been nearly 2 full decades since you could picture the Patriots separate from Thomas Edward Brady.
Like most sports fans most of us selfishly wanted to see the guy go out not just a champion, but more importantly a Patriot. I’d be lying if I said watching him these next few years in different colors won’t induce vomiting and spoil the legacy. The gag reflex kicks in even now just thinking about it. But I’ll be damned if I’m not rooting like hell for the guy to light it up next year.
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I held it together for a while yesterday but sometime in the afternoon around the hundredth or so text from one of those people who only texts you on Christmas, asking me “what do you think about Brady?” I snapped. But it got me thinking about how many other greats chose to keep it moving, literally, rather than hang it up and call it career with one team.
I started with the obvious ones then fell down a real rabbit hole. I went a little crazy posting on twitter but I’m glad I did because people tweeted some incredibly obscure ones I either completely forgot or never even knew about.
Below is a list I compiled of the top 29. Warning in advance this blog is long as hell. But what the hell else does anybody have to do right now?
Feel free to weigh in or add anybody I forgot in the comments.
29- Sammy Sosa (Texas Rangers)
Man. For a guy who arguably had the world by balls 5 years prior, things got rough and they got rough quick for Slammin’ Sammy. Exiled by the team for which he was the poster boy of, helped save baseball with, and almost took to the World Series, the Cubs, in 2006 Sosa found himself back where it all started for him 18 years earlier; the Texas Rangers. Not only did Sammy not get to go out a Cub, but to this day he’s not welcomed back at what is quite possibly the friendliest place in all of sports – Wrigley Field. That’s like being blacklisted from Disney Land. Fun Fact - Baseball experts to this day are left wondering how a guy who hit 64 home runs in only 577 ABs 6 years prior was only able to manage 14 in 425 plate appearances in 2007. The world may never know.
28 – Shaquille O’neal (Boston Celtics)
Shaq got around. Laker all time great yah yah but did you know he played for 6 teams in his career. Bet you forgot or didn’t know he had a couple lost seasons with the Phoenix Suns in 07 (33 games) and 08 (28 games). Then it was on to Cleveland where he averaged 20 minutes playing and 12 points before getting thumped by the Celtics in the 2nd round of the playoffs. To the luck of Celtics fans and benefit of children in hospitals all around Boston he decided to keep playing and signed with the Celtics in 2010 where he appeared in just 37 games. He was of course a fan favorite and in his short time with the Celtic’s left a huge mark on the city with his charity work and frequent children’s hospital visits.
27 – Phil Esposito (New York Rangers)
I promise this isn’t becoming a Boston-centric blog. Phil started his career in Chicago with his brother Tony but nobody remembers him for that. They remember him for ushering in the era of the Big Bad Bruins in the 1970’s with Bobby Orr. And more importantly for his hair. Look at this guys perfectly coiffed do. And those sideburns. Damn. Phil Esposito was sex on skates. Legend has it that Espo and Derek Sanderson took down ¾ of the New England female population from 1969-1972. But back to hockey. Before Espo became crazy in his later years, he was a stud on the ice too. In 1973 he was responsible for 135 Points. And that is with Bobby Orr (ever heard of him?) putting up 145 of his own. For some reason the Bruins wanted to cut his shifts the following year so he demanded a trade. They sent him to New York where he continued to light the lamp leading the Rangers in goals each of his 6 seasons there. Fun fact – my first ever hockey game I attended was Phil Esposito night at the old Boston Garden. I had no idea what was going on because I was so young but they retired his number into the rafters and it was a huge deal because the young superstar assistant captain Ray Bourque wore Esposito’s 7 at the time. He took off his jersey to unveil his new number 77 underneath and “give” Esposito his number back. The place went nuts. There was nothing like old sports arenas/stadiums.
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26- Patrick Ewing (Orlando Magic)
Tough look for the Hoya Destroya here. But not a surprising one. Coming up just shy of winning a championship in 1994 (Jordan’s off year) losing to the Rockets in 7 games, Ewing never got another shot. So how does the NBA’s marquee franchise treat its face of the franchise for 15 seasons? By shipping him off to Seattle. Where he withered away before winding up in Orlando the following year (2002) where he was even more irrelevant (13 mns/6pts). No bueno for a guy who rescued a team from obscurity and made them a powerhouse every year for a decade while having to go up against MJ, Pippen, and co. For those 6 (yes 6) epic Bulls-Knicks playoff matchups alone from 1988-1996 we owe Ewing a huge thank you for carrying those Knicks teams on his back and giving Jordan’s Bulls a hell of an opponent and the last real “villain” team we might ever see in the NBA. Fun Fact – In the 1st Edition of The NBA JAM arcade game (not tournament edition) the Knicks’ Ewing/Starks team was almost unstoppable. They made video game John Starks way better in that game than he actually was. Guy was unconscious from 3, stole everything, and knocked everybody on their ass.
25 – Deion Sanders (Baltimore Ravens)
One of the greatest athletes of all time just couldn’t walk way from the game. Could anybody really blame him? The guy was the center of attention from his last season at FSU, through the Yankees/Braves/Falcons years (such a fucking awesome 30-for-30), then wound up on the national favorites San Fransisco 49er’s through free agency. While in San Fran the guy won defensive player of the year, pick-sixed (full beer) Jeff George while staring down his old teams sideline on the return. Got in a fight with Andre Rison, and won a Super Bowl. Sprinkle in a few massive Nike ad campaigns and this guy was a household name. As if all that wasn’t enough Prime Time then orchestrated the “Deion Sweepstakes” in which he ended up signing the highest paying defensive player deal at the time to go to Dallas, “America’s Team”. In Dallas he worked out a deal where he would be able to play both ways. He won another Super Bowl with the Cowboys and made 5 pro bowls. In a salary cap move he was released in 2000 and signed to a ridiculous deal by Dan Snyder and the Redskins. Obviously. He could only put up with Snyder’s circus for one year he and retired after a statistically impressive season. (Daniel Snyder has got to be the absolute worst). After being retired for 4 years and at the age of 37 he came back in 2004 to join his friend, alleged murderer Ray Lewis in Baltimore. After two dismal seasons he finally hung em up. Fun Fact – On a network full of huge ego’s and alpha’s (NFL Network) Deion is an absolute delight to listen to. He gives it to the viewer straight, doesn’t have an agenda or ax to grind with anybody, and his predictions are usually spot on.
24 - Pedro Martinez (Philadelphia Phillies)
What is there to say about Pedro Martinez that hasn’t already been said? The greatest pitcher I’ve ever witnessed during my life. What he did in Boston with under dog Red Sox teams in the late 90s-early 2000’s against a Yankees dynasty was incredible. Him coming in from the bullpen in game 5 of the 1999 DS against Cleveland to shutdown a powerhouse Indians lineup who had already scored 8 runs, while injured, over six scoreless innings still gives me chills. Pull it up on Youtube. (LINK https://www.youtube.com/watch?v=8X0EpWLPupI) In 2004 after finally winning a World Series in Boston he left to head to the Mets where he had an injury riddled frustrating 4 seasons. In 09 he signed in mid season with the Phillies where he ended up losing 2 games in the World Series to the Yankees before calling it a career. Fun Fact – 1999 All-Star Game. Fenway Park. (LINK - https://www.youtube.com/watch?v=CD_c-oawu68) Pinnacle of the steroid era. 6 batters up – Larkin (K), Walker (K), Sosa (K), McGwire (K), Williams (E4, CS), Bagwell (K). 5 Strike Outs, 0 Hits. Unreal moment.
23. Frank Thomas (Oakland A’s)
This was one of those head scratchers that somebody sent to me on twitter that I honestly had no idea about. I remember Frank Thomas being unstoppable in the early 90s and then being screwed out of an MVP season and Triple Crown in 1994 by the strike. He sustained success the next couple seasons but then injuries began to catch up to him and his demand to play in the field rather than full time DH set him back. Sadly he fizzled out and wasn’t even on the World Series roster in 2005 when the White Sox smoked the Astros*. He signed an embarrassingly meager deal with Oakland in 2006 and went off hitting 39 HRs and driving in 114 RBI. He finished second in comeback player of the year voting. Coming off this hot season the Toronto Blue Jays signed Thomas to a 2 year $18 million deal. He’d go on to hit his 500th HR before being released and winding up back in Oakland where he wrapped up. (Yah he signed a 1 day contract to retire a White Sox but that’s theatre). Fun Fact – Fairly certain White Sox Dave would lay down on train tracks if Frank told him to.
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22- Nomar Garciaparra - (Oakland A’s) Oakland
Where heroes get put out to pasture? Yes we all know Nomar was victim of one of the most heart wrenching turn of events in baseball history. During his tenure with the Red Sox this guy was inarguably the biggest deal in Boston. This was while Tom Brady was winning 3 Super Bowls with the Patriots. He WAS the Red Sox. For crying out loud the guy held Ted Williams hand at that 1999 All Star Game and helped him throw out the first pitch!
But right before the trade deadline in 2004, coming off a nagging heel injury that dramatically affected his range, the Red Sox packaged him in a 4 team deal and sent him to the Cubs. Ever the professional he thanked the Red Sox and all the fans for everything on his way out. Then sat back and watched the Boston team he led for 8 seasons snap their 100 year curse and win the World Series. Brutal. He stayed in Chicago another year. Suffered more injuries. Headed out west to the Dodgers and eventually the A’s. Fun Fact – Ask anybody in their 30s from Boston to do Nomar’s in between pitch routine and 99.9% chance they know it by heart.
21- Joe Namath (Los Angeles Rams)
Another one I saw a picture of and had to check if it was photo shopped. Only the New York Jets could let the only player of theirs anybody would ever associate with greatness (in reality the guy was a pick machine with a career 65.5 passer rating) leave in his final year to retire somewhere else. Broadway Joe was forced to take his talents to LA after being WAIVED by the Jets. Unbelievable. Fun Fact – Just Watch:
20- Ron Santo (Chicago White Sox)
This guy bled Cubbie blue for 13 years. He patented the heel click. He invented the ear flaps on batting helmets. He was a double play machine. Multiple times setting and breaking his own single season record for third basemen. He did this all while HIDING THE FACT he was diabetic. Think about that. He was so afraid that if his teammates or opponents knew he’d be forced to retire. He was also the first player to ever exercise a trade veto. The Cubs were so intent on trading him that the nice guy he was he requested the team to keep him in Chicago and trade him to the White Sox. Where he rode the bench and occasionally played second base. Poor guy lost his legs in the early 2000’s and lost his battle to the disease in 2004. Fun Fact – I’ve known Barstool Carl for longer than I would like to admit. And his family. They are rabid south side White Sox fans. I could never figure out how or why he was such a diehard Cubs fan. The day I asked him he went into one of the most well-said, beautiful explanations as to why and it all centered around Ron Santo. Gotta get him to tell it sometime if he hasn’t already numerous times on RLR.
19 & 18- Paul Pierce & Kevin Garnett - (Los Angeles Clippers, Minnesota Timberwolves* Brooklyn Nets)
Haters will have a bone to pick with me here. Don’t care. Technically The Truth and KG retired playing for their hometown team (Pierce, Clippers) and the team they came in with and were apart of for 12 years (KG, T’Wolves) but they’ll always be remembered as going out with the Nets. The only guy possibly more ruthless than Bill Belichick might be Danny Ainge (I still love you Perk) and in a coldblooded move he dealt the remaining 2 of the Big Three to Brooklyn for a pick that ended up being perennial Summer League participant James Young (now out of the league). And two other guys named Jaylen Brown and Jason Tatum. Whatever.
The Sports Illustrated cover with KG, Pierce, Jason Kidd, Joe Johnson, and Deron Williams remains one of the grossest things these eyes have ever seen. Sure Pierce got to go to LA to ride off into the sunset and if you want to call suiting up for 5 games in Minnesota “playing” for the Timberwolves then yah Garnett retired a Timberwolf. But this is the image that will always sting.
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17 – Yogi Berra (New York Mets)
First generation American. The embodiment of the American dream. World War 2 Normandy Beach hero. Purple Heart recipient. Presidential Medal of Freedom Recipient. 10 time World Series Champion. Ten! Hall of Famer. Number 8 retired by the Yankees. World famous “malapropist”. Banished by the Yankees after taking them to the World Series in 1964 as a player/manager to the cross town Mets. A dumpster fire of an organization even back then. Berra once again proved his talent as manager of the Mets taking them to the 1973 World Series coming up short in 7 games to Oakland. Fun Fact – Yogi loved bowling. Big time bowler. Heard that was popular around here. Even opened a series of lanes with former teammate Phil Rizzuto after they both retired.
16 – Martin Brodeur (St. Louis Blues)
I don’t know much about this guy other than that 1- he was a fucking stud. 3 time Stanley Cup Champion, 2 time Gold Medal Winner (Team Canada), 4 time Vezina Trophy winner, all time league leader in wins (691), 2- for a goalie he could dangle (no joke), and 3 – he was teammates with one of the biggest scumbags in the history of the world Claude Lemiuex. In all seriousness Brodeur was a brick wall basically all through the 90’s. After the lockout season in ’95 I remember the Devils developed this trap style of play and dominated. They also pretty much ruined hockey for casual fans because it slowed the game down and cut the ice in half. Miserable to watch. Anyway, Brodeur won 3 Cups with the Devils and racked up almost 7 wins which is insane. There was no falling out and he wasn’t traded. He just didn’t want to retire so he took a try-out with St. Louis in 2014 after their starter went down and retired halfway through the season. Just bizarre seeing him in a Blues jersey.
15 - John Smoltz (St. Louis Cardinals)
Totally forgot about this one. Everybody with a pulse knows John Smoltz as the Braves great/scratch golfer turned soothing voiced announcer on MLB Network. Not everybody remembers his disastrous 2009 season with the Red Sox in which he was DFA’d in August. I thought it was over for him then. But apparently he headed to St. Louis where he was 1-3. He retired at the end of the season. Fun Facts – John Smoltz is BFF’s with Doc Rivers and Jeff Foxworthy. He’s an accomplished accordion player. And Tiger Woods claims he’s the best golfer not on the PGA tour. No big deal.
14- Manny Ramirez (Tampa Bay Devil Rays* Chicago White Sox)
The player many call the best right handed hitter of his generation and possibly ever. 2 time world Champ. All time post season HR leader. Came into the league like a bat out of hell with Cleveland. Signed a huge free agent deal with Boston in 2001 and was a Red Sock til he started to pack on the pounds and his production began to slide in 2008. The Red Sox dealt him to the Dodgers midway through the season for Jason Bay. Then there was this whole banned substance thing… and you know. Manny bounced around towards the twilight of his career between the White Sox, and then Tampa Bay. I claimed he retired a Devil Ray on twitter and White Sox Dave blew up with texts informing me I was wrong. Said that he signed a one year deal to retire with the White Sox and told me “to ask Ozzie” about the story because “its hilarious.”
Fun Fact – People forget that out of all the crazy shit Manny’s done perhaps the best and most under rated was the time he auctioned his grill off on eBay. This was during the early internet days. I think Dave was still just doing Daily Thoughts back then but this was peak Manny being Manny. Check out these pictures. (https://www.cnet.com/news/update-manny-ramirez-goes-from-rbis-to-ribs/)
13- Hakeem Olajuwan (Toronto Raptors)
Wanna talk about ruthless? This one was tough. After emigrating from Lagos to Houston to play college ball at The University of Houston, he was mentored by Moses Malone, formed Phi Slamma Jamma with Clyde the Glide and went to two straight NCAA Title Games (lost both). He got drafted #1 overall by the Rockets where he helped them win back to back NBA Championships and played his entire career. Until 2001 when he was negotiating a new deal and turned down a 3 year $13 million deal and the Rockets turned around and dealt him to the Raptors for a couple draft picks. Fun Fact – Olajuwon didn’t pick up a basketball until he was 16 years old.
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12- Jeremy Roenick (San Jose Sharks)
One of the greatest American born hockey players of all time. Also one of the toughest guys to ever lace them up. Burst into the league in 1988 with the Blackhawks and making a Stanley Cup Final in 1991. He showed real promise as a great all around player and scored 50 goals in 2 of his first 4 full seasons with the Blackhawks. Monster hits, mainly from Derian Hatcher, derailed his career along with the misfortune of playing for one of the worst owners in sports. The Hawks sent him to Phoenix which later found him in Philadelphia, then LA, then Phoenix again, and finally in San Jose where he was a checking line center. Beloved teammate on the ice and loved just as much off the ice it’s sad to think about what could have should have been for Roenick.
11- Chris Chelios (Detroit Red Wings* Atlanta Thrashers)
This ones going to be controversial. I’m well aware. Here’s the deal with Chelios. Everybody wants to argue he is remembered more for his time and success in Detroit than in Chicago. The issue is he was born in Chicago. Grew up here. Grew up hating the Red Wings. When he was captain of the Blackhawks he despised the Red Wings even more. And rightfully so. They were basically the Red Army. I can’t find the quote anywhere but I remember him claiming if the Blackhawks ever traded him (which they did) the only team he wouldn’t want to play for was Detroit. Of course he ends up getting dealt to Norris Division rival Detroit and immediately becomes Mr. Red Wing. Opens up a really sweet shit hole dive bar named Cheli’s in a spot that would eventually become prime real estate next to Ford Field and Comerica Park (rumor is Red Wings & Tigers owner Mike Ilitch owned the property before Chris. Weird). Am I jealous of this? Yes, very.
He refuses to retire at age 50 so he plays for the Chicago Wolves and somehow the Atlanta Thrashers but I’m refusing to acknowledge them as an NHL team. Then he goes back after retirement to join the Red Wings coaching staff. I get Bill Wirtz was as bad as bad gets in terms of owners. But come on man, come home at some point.
10- Willie Mays (New York Mets)
Obviously I never got the honor to watch Willie Mays play baseball. But man do I wish I did. My uncle claims he was the only player he ever saw who was better than Mickey Mantle. His stats attest. Speed, power, range for days, glove and arm off the charts. Guy was the epitome of a five tool player. Hand up I had zero idea Mays went out a Met. Upon reading why it was pretty heartbreaking but not surprising given the life players had back in 60s and 70s. In 1972 the Giants were losing money and afraid they couldn’t make payroll. They couldn’t guarantee Mays a pension after he retired. He was 41. In 1963 Mays signed a record setting deal for $105,000. Yes, one comma. That was after winning the first of two MVP’s and a World Series title. So hard up for financial security he accepted a trade back to New York. His body was failing him but he still managed to appear in 133 games over a season and a half with the mets. Reading stories of him falling down in the outfield, and struggling to run out in field ground balls sucked to picture. Reading him comment "growing old is just a helpless hurt." sucked more. Good news is after he retired he got a big endorsement deal with Bally’s in Atlantic City which cost him his standing temporarily with MLB (shocker) but secured him financially. He’s also a special assistant with the Giants so its good to know they made right by him later in life. Fun Fact – Mays still holds the record with 7,095 putouts. Let that number sink in. Insane.
9- Emmitt Smith (Arizona Cardinals)
This was a weird one. I was always indifferent towards Emmitt Smith. I hated the Cowboys but didn’t hate him. I thought he was good don’t get me wrong but not great. I thought he benefitted from an incredible line and team in general and I thought Thurman Thomas was better. And that Barry Sanders was better than both of them. But back to Emmitt. He still holds the all time rushing record, which he passed Walter Payton for in 2002. That’s obviously big time and worthy of admiration. But when Bill Parcells rolled into town that offseason and in classic Parcells fashion announced “We’re going with younger players.”, why not just call it career? There was nothing else to prove. He was able to eek out 1000 yards over 2 seasons in Arizona but was it worth having these images in these red jerseys forever?
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8- Brett Favre (Minnesota Vikings)
Talk about indecisiveness. You think its impossible getting your girlfriend or wife to pick a place she wants to go to dinner? Or make any simple decision in general so that you aren’t forced to and inevitably get crucified for it later? Show me the most indecisive woman in the world and Brett Favre will ask you to hold his spitter. The guy spent the last ten years of his career holding the country hostage (via his pals at ESPN (they lie)) on his “Decision”. Everybody knew he was going to play but what fun would it be to just sign a multi-year deal, or announce at the end of the season you’ll be back at training camp in a few months? Nah, you gotta milk the shit out of it media wise, keep your teams front office up in the air in terms of draft preparation, and keep your backup QB, who you treat like shit, wondering if and when he’s going to be handed the reigns. (PSA – Fuck Aaron Rodgers, but fuck Brett Favre for treating him even worse than Tom Brady treated Jimmy G). This went on for years. Seriously, remember back. It was nauseating. He actually retired at one point which was really confusing because he was crying saying he knew he could still play. Then a few months later asked the Packers to release him. Um what? Then went on Fox News with Greta Van Susteren (yes this really happened) and said he was “guilty of retiring too early” because “the Packers had pressured him into it” and the proceeded to throw the entire organization under the bus. Somehow he had the balls to roll into training camp. But Mike McCarthy and Ted Thompson finally grew some balls and told Favre to hit the bricks.
To the mighty New York Jets Favre went. Where he threw 22 picks with a record of 9-7.
From there it was on to Minnesota where he had one of the best seasons of his career in 2009 leading the Vikings to an NFC Championship overtime loss against the Saints. So it wasn’t a complete wash-out for Favre in terms of life after Green Bay. But the way he dragged everything out and went about it will be what everybody remembers.
Fun Fact – Brett Favre is an accomplished self portrait photographer. Google his work.
7- Ray Bourque (Colorado Avalanche)
I know I’m going to get killed by the Boston people on this one but hear me out. This wasn’t bad for the reasons you’re thinking. Did Ray Bourque deserve to win a Cup? More than anybody. Was it criminal that he wasn’t able to do it in Boston because Harry Sinden threw nickels around like they were manhole covers? Absolutely. So it took trading him to a startup team named the Avalanche for him to do it. If the Nordiques had stayed in Quebec and the Bruins sent him to win one where he grew up that would have been poetic. But this one just seemed cheap. Like KD winning with the Warriors,or Revis winning with New England. Hammer me all you want.
6- Karl Malone (Los Angeles Lakers)
Speaking of cheap titles how about Karl Malone? Malone was always a stand up guy and one of the best players of all time with the Jazz. But he could never get over the hump. So in what he decided would be his final year he decided to go all in and join the Lakers (along with Gary Payton) to win a title. Small problem was they ran into a buzzsaw in the Detroit Pistons. They were almost swept in the Finals and Malone called it a career.
Fun Fact – Karl Malone wrestled in a WCW Bash at The Beach Pay Per View match in 1998 with Diamond Dallas Page vs Dennis Rodman & Hollywood Hulk Hogan. (LINK - https://www.wwe.com/videos/karl-malone-diamond-dallas-page-vs-dennis-rodman-hulk-hogan-bash-at-the-beach-1998)
5- Jerry Rice (Seattle Seahawks)
When you think of the words “No quit” you need to think of Jerry Rice. This man had to be dragged off the field pretty much. Everybody knows about his fairy tale career in San Francisco teaming up with Joe Montana and Bill Walsh to solidify himself as the greatest receiver of all time. But many forget that in 2000 the writing was on the wall that the Niners were looking to make Terrell Owens their featured receiver so Rice bolted across the bay to Oakland. There he put up 1000 yard receiving seasons and even made the pro bowl in 2002. In 2004 he was traded to the Seahawks for a 7th round pick (insulting). Seatlle wasn’t interested in bringing him back the next year but the Denver Broncos were, even though was 42 years old. Learning that he’d be at the bottom of their depth chart made him change his mind and pulled the the one day contract with San Fran move.
Fun Fact – As a kid he developed his speed by chasing down horses in the pasture. He developed his hands by catching bricks. True story.
4- Joe Montana (Kansas City Chiefs)
Of course this is the one everybody is comparing to the Brady situation. It couldn’t be further removed. Montana’s final years in San Fran were spent nursing a really bad elbow injury and watching Steve Young step into the starting role and not missing a beat. The entire team became comfortable with him and assumed they had “moved on” from Montana. Sucks but that’s the way it is. Much like the Drew Bledsoe Tom Brady transition. Circle of life. Montana regained his health and expected to step back into the starting role. Which was a problem considering he was actually then 3rd on the depth chart behind Young and STEVE BONO.
So in typical Notre Dame grad fashion when he didn’t get his way he stomped his feet and demanded a trade. The Niners sent him to the heart of flyover country, Kansas City. Along with newly acquired Marcus Allen, the Chiefs made some noise in Montana’s first year (1993) reaching the AFC Championship where they lost to Buffalo. Montana even made the pro bowl. The following year didn’t go as well as the Chiefs were knocked out of the wildcard by the Dolphins causing Montana to finally say goodbye.
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Fun Fact – Joe Montana was once considered the greatest quarterback of all time.
3- Bobby Orr (Chicago Blackhawks) As Rear Admiral put it yesterday, posting that picture “is a hate crime”
Turns out how Bobby Orr ended up becoming a Blackhawk in the twilight of his career was actually a crime. After a lost season due to knee injuries in ‘74 Orr knew this next contract would be his last. He trusted his agent Al Eagleson to handle all negotiations for him. Never sitting in any of the discussions he was completely unaware that the Bruins were offering Orr not only a multimillion dollar deal (unheard of in that era) but also an 18.5% ownership stake in the team (can you imagine that today?). Eagleson, being a close buddy of Blackhawks owner Bill Wirtz, simply told Orr the Bruins were low-balling him and that Chicago had an offer he couldn’t refuse. Orr was disappointed but trusted Eagleson and signed with Chicago. Karma and the law would eventually come for Eagleson in 1998 as he was sentenced to 18 months in jail and fined $700,000. Once Orr learned the truth he never spoke to Eagleson again. Prolonged knee injuries allowed orr to play only 26 games with the Blackhawks over three seasons having to retire at the age of 30. Robbed of a career and robbed of an ownership stake.
Fun Fact – Bobby Orr was so good that when he retired the Hall of Fame waived the waiting period for him and inducted him that year.
2- Tom Brady (Tampa Bay Buccaneers)
This one stings for a lot of reasons. You might be able to relate to this being a Bulls fan in the 90’s but even that was different because MJ retired and then came back after a hiatus. The thing about this is it isn’t easy to understand unless you’ve been a Patriots fan since before Brady arrived.
I apologize in advance for the sexist metaphor but it’s the best way I know how to describe Patriots fandom in this situation.
Watching Tom Brady leave to go to the Tampa Bay Bucaneers is like watching the girl you started dating freshman year of highschool that started out as innocent girl next door cute (OG Stoolies would call her a potato sack girl), but got progressively hotter every year to the point she now looks like Sierra Skye
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…who would go to parties but never drink, was a 2 sport varsity athlete, was class Valedictorian, went to MIT undergrad, Harvard Law, who won the Nobel Peace Prize, and the Presidential Medal of freedom, break up with you and immediately start dating a meth addict. From Tampa Bay. It fucking hurts. And it hurts bad.
And the worst part of it all?
You can’t even be mad at Brady in this scenario. He gave us everything. Year after year after year. He took pay cuts repeatedly. Gladly. All he asked was spend the money to assemble the best team possible around him. And what did BB and RKK do? Enjoyed being well under the salary cap year after year while trotting out the island of misfit toys for Brady to turn into all pro’s. Supposedly the straw that broke the camels back was Diggs’ getting traded to the Bills after Hopkins went to Arizona. Not the insulting 1 year offer Belichick proposed, but the fact he wants to win SO badly that he can’t bare to sit by another off season and watch the best weapons wind up everywhere else in the league.
Good luck TB12. Sorry it had to end like this.
1- Michael Jordan (Washington Wizards)
The Chicago Bulls, namely Jerry Krause, were lucky in the sense that when they were winning their championships and the squad was disbanding the social media was non existent, and the 24 hour round the clock sports culture was in its infancy. Otherwise there is no chance Jerry Krause would have got the free pass he did. The only real inside details you can get on the behind the scenes dealings that went on between all the enigmatic personalities making up those 1990’s Bulls teams is from the numerous books written about them. “The Jordan Rules”, “Playing For Keeps”, “Blood on the Horns”. All of them carry the same overall theme. Jordan was a prick, Rodman was nuts, Pippen just wanted to be appreciated, Jackson was the peacekeeper, Reinsdorf only cared about winning, and Krause was an enormous piece of shit. Nobody liked the guy. In fact everybody hated the guy. They went out of their way to make it known to him.
Jordan made it abundantly clear that he would come back if Jackson was still the coach. Krause made it clear midway through the season that not only wouldn’t Jackson be back but that he already had his replacement lined up (Tim Floyd). So the band broke up. Jordan kidded himself that he was done with the game for a year before lacing them back up for the Wizards (woof).
The worst part of all this will always be the “what if?”
What if MJ didn’t retire that first time? Do the Bulls win 8 straight? (Yes)
What is Jackson and Jordan stayed on another couple years. Could they have won 10 straight? (Yes)
Like everybody else on the planet I can’t wait for this 10 part Jordan special on ESPN to come out. Not just so we can all stroll down memory lane again and be reminded of how how truly incredible MJ was. But more so that the younger generation that wasn’t lucky enough to grow up watching him can get a real taste of what his true greatness was like. So they never make fools out of themselves asking if Lebron, or anybody for that matter, is better than Jordan again.
Fun Fact – In the original “Jumpman” photo Jordan is wearing New Balance’s.
HONORABLE MENTION
- Dwayne Wade – We all know. Local Chicago (er, Robbins) kid, returns home to finish out career on the team he grew up dreaming to play for. But it doesn’t negate the fact that at the time he swindled Gar/Pax into outbidding the heat and dropping 47 mil over 2 years on him he was about 2-3 years past the point where he should have hung it up. Not only that, but after the Bulls bought him out following a 60 game effort in 16/17 Wade got his buddy Lebron to convince David Griffin to take a flyer on him and bring him to Cleveland. Wade could barely play at that point and dressed for less than half the seasons games and appeared in even fewer. He found his way back to Miami in 2018 and found new life. Playing in 72 games he averaged 15 per game
- Kerry Wood – Did you know Kerry Wood was Yankee? I did not. This picture messed my head up.
- Scottie Pippen – Pippen almost retired a Rocket before the Bulls did the right thing and brought him back.
- Jack Parkman – Poor guy ate shit on all those abysmal Indians teams then leaves to go to the White Sox only to get beat by them in one of the wildest finishes in history.
- Vlad Guerrero – I remembered the Rangers year. Had no clue he finished up in Baltimore. Poor guy.
- Allen Iverson – Bounced around Denver, Detroit, Memphis, and then back to Philly before finally calling it quits. Most underappreciated player of his generation. Warrior.
- Ken Griffery Jr. – It should have been against the law for Griffey to play anywhere other than Seattle. He put the Mariners on the map. His swing. His swagger. His acrobatic catches. The fact that even with all the major injuries he suffered he still hit 630 home runs is mind boggling. Another one of the great “what if” he stayed healthy?